1888:
1677:, in trans by distinct enzymes, referred to as tailoring enzymes, to become biologically active (Figure 3). To convert the linear heptapeptide to cross-linked, glycosylated vancomycin, six enzymes, are required. The enzymes OxyA, OxyB, OxyC, and OxyD are cytochrome P450 enzymes. OxyB catalyzes oxidative cross-linking between residues 4 and 6, OxyA between residues 2 and 4, and OxyC between residues 5 and 7. This cross-linking occurs while the heptapeptide is covalently bound to the PCP domain of the 7th NRPS module. These P450s are recruited by the X domain present in the 7th NRPS module, which is unique to glycopeptide antibiotic biosynthesis. The cross-linked heptapeptide is then released by the action of the TE domain, and methyltransferase Vmt then
1718:
1643:(PCP) domain, and a condensation (C) domain. In the A domain, the specific amino acid is activated by converting into an aminoacyl adenylate enzyme complex attached to a 4'phosphopantetheine cofactor by thioesterification. The complex is then transferred to the PCP domain with the expulsion of AMP. The PCP domain uses the attached 4'-phosphopantethein prosthetic group to load the growing peptide chain and their precursors. The organization of the modules necessary to biosynthesize Vancomycin is shown in Figure 1. In the biosynthesis of Vancomycin, additional modification domains are present, such as the
824:
866:
InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
745:
722:
40:
1659:
1889:
1779:-Ala peptide motif of the peptidoglycan precursor, thereby preventing its processing by the transglycosylase; as such vancomycin disrupts the transglycosylation activity of the cell wall synthesis process. The disruption leads to an incomplete and corrupted cell wall, which makes the replicating bacteria vulnerable to external forces such as osmotic pressure, so that the bacteria cannot survive and are eliminated by the immune system.
1593:
1670:β-hydroxytyrosine (β-HT) is synthesized prior to incorporation into the heptapeptide backbone. L-tyrosine is activated and loaded on the NRPS VpsD, hydroxylated by OxyD, and released by the thioesterase Vhp. The timing of the chlorination by halogenase VhaA during biosynthesis is currently undetermined, but is proposed to occur before the complete assembly of the heptapeptide.
31:
4210:
1405:
which allows to measure vancomycin levels in the blood and tailor the dosage accordingly. TDM using area under the curve (AUC)-guided dosing, preferably with
Bayesian forecasting, is recommended to ensure that the AUC0-24h/minimal inhibitory concentration (MIC) ratio is maintained above a certain threshold (400-600) associated with optimal efficacy.
1817:
7820:
496:)- 48- {oxy}- 4,5- dihydroxy- 6- (hydroxymethyl)oxan- 2- yl]oxy}- 22- (carbamoylmethyl)- 5,15- dichloro- 2,18,32,35,37- pentahydroxy- 19- - 20,23,26,42,44- pentaoxo- 7,13- dioxa- 21,24,27,41,43- pentaazaoctacyclopentaconta- 3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49- pentadecaene- 40- carboxylic acid
1620:
1494:
Plasma level monitoring of vancomycin is necessary due to the drug's biexponential distribution, intermediate hydrophilicity, and potential for ototoxicity and nephrotoxicity, especially in populations with poor renal function and/or increased propensity to bacterial infection. Vancomycin activity is
1367:
Vancomycin is recommended to be administered in a dilute solution slowly, over at least 60 min (maximum rate of 10 mg/min for doses >500 mg) due to the high incidence of pain and thrombophlebitis and to avoid an infusion reaction known as vancomycin flushing reaction. This phenomenon has
1305:
Importantly, the risk of AKI increases with co-administration of other known nephrotoxins, in particular, aminoglycosides. Furthmore, the sort of infections treated with vancomycin may also cause AKI and sepsis is the most common cause of AKI in critically ill patients. Finally, studies in humans are
1338:
are even more difficult due to the scarcity of quality evidence. The current consensus is that clearly related cases of vancomycin ototoxicity are rare. The association between vancomycin serum levels and ototoxicity is also uncertain. While cases of ototoxicity have been reported in patients whose
1176:
Serum vancomycin levels may be monitored in an effort to reduce side effects. Still, the value of such monitoring has been questioned. Peak and trough levels are usually monitored, and for research purposes, the area under the concentration curve is also sometimes used. Toxicity is best monitored by
1309:
Animal studies have demonstrated that higher doses and longer duration of vancomycin exposure correlates with increased histopathologic damage and elevations in urinary biomarkers of AKI.37-38 Damage is most prevalent at the proximal tubule, which is further supported by urinary biomarkers, such as
1767:
Peptidoglycan is a polymer that provides structural support to the bacterial cell wall. The peptidoglycan precursor is synthesized in the cytoplasm and then transported across the cytoplasmic membrane to the periplasmic space, where it is assembled into the cell wall. The assembly process involves
1666:
A set of NRPS enzymes (peptide synthase VpsA, VpsB, and VpsC) are responsible for assembling the heptapeptide. (Figure 2). VpsA codes for modules 1, 2, and 3. VpsB codes for modules 4, 5, and 6, and VpsC codes for module 7. The vancomycin aglycone contains 4 D-amino acids, although the NRPSs only
1445:
The only approved indication for oral vancomycin therapy is in the treatment of pseudomembranous colitis, where it must be given orally to reach the site of infection in the colon. Following oral administration, the fecal concentration of vancomycin is around 500 μg/mL (sensitive strains of
1404:
Dose optimization and target attainment of vancomycin in children involves adjusting the dosage of the antibiotic to maximize its effectiveness while minimizing the risk of adverse effects, specifically acute kidney injury. Dose optimization is achieved through therapeutic drug monitoring (TDM),
1400:
The recommended intravenous dosage in adults is 500 mg iv every 6 hours or 1000 mg every 12 hours, with modification to achieve a therapeutic range as needed. The recommended oral dosage in the treatment of antibiotic-induced pseudomembranous enterocolitis is 125 to 500 mg every 6
1301:
The extent of nephrotoxicity for vancomycin remains controversial. In 1980s, vancomycin with a purity > 90% was available, and kidney toxicity defined by an increase in serum creatinine of at least 0.5 mg/dL, occurred in only about 5% of patients. However, dosing guidelines from the
6220:
The first reports of vancomycin-resistant enterococci (later classified as VanA type of resistance) involved strains of E. faecium that were resistant to vancomycin and teicoplanin (another glycopeptide) and that were isolated from patients in France and
England in 1986. Vancomycin-resistant E.
6728:
1288:
Historically, vancomycin has been considered a nephrotoxic and ototoxic drug, based on numerous case reports in the medical literature following initial approval by the FDA in 1958. However, as the use of vancomycin increased with the spread of MRSA beginning in the 1970s, toxicity risks were
4718:
Rybak M, Lomaestro B, Rotschafer JC, Moellering R, Craig W, Billeter M, et al. (January 2009). "Therapeutic monitoring of vancomycin in adult patients: a consensus review of the
American Society of Health-System Pharmacists, the Infectious Diseases Society of America, and the Society of
2180:
The compound was initially called compound 05865, but was eventually given the generic name vancomycin, derived from the term "vanquish". One advantage that was quickly apparent was that staphylococci did not develop significant resistance, despite serial passage in culture media containing
1352:
Another area of controversy and uncertainty concerns the question of whether, and if so, to what extent, vancomycin increases the toxicity of other nephrotoxins. Clinical studies have yielded variable results, but animal models indicate some increased nephrotoxic effect probably occurs when
1782:
Gram-negative bacteria are insensitive to vancomycin due to their different cell wall morphology. The outer membrane of Gram-negative bacteria contains lipopolysaccharide, which acts as a barrier to vancomycin penetration. That is why vancomycin is mainly used to treat infections caused by
1302:
1980s until 2008 recommended vancomycin trough concentrations between 5 and 15 μg/mL. Concern for treatment failures prompted recommendations for higher dosing (troughs 15 to 20 μg/mL) for serious infection, and acute kidney injury (AKI) rates attributable to the vancomycin increased.
6889:
1768:
two enzymatic activities: transglycosylation and transpeptidation. Transglycosylation involves the polymerization of the peptidoglycan precursor into long chains, while transpeptidation involves the cross-linking of these chains to form a three-dimensional mesh-like structure.
4540:
1343:
of vancomycin for the purpose of maintaining "therapeutic" levels will prevent ototoxicity also remains unproven. Still, therapeutic drug monitoring can be used during vancomycin therapy to minimize the risk of ototoxicity associated with excessive drug exposure.
6882:
6827:
Martin VT, Zhang Y, Wang Z, Liu QL, Yu B (January 2024). "A systematic review and meta-analysis comparing intrawound vancomycin powder and povidone iodine lavage in the prevention of periprosthetic joint infection of hip and knee arthroplasties".
1688:
Some of the glycosyltransferases capable of glycosylating vancomycin and related nonribosomal peptides display notable permissivity and have been employed for generating libraries of differentially glycosylated analogs through a process known as
5777:
1525:
of 10 to 15 mg/L or 15 to 20 mg/L, depending on the nature of the infection and the specific needs of the patient, may be appropriate. Using measured vancomycin concentrations to calculate doses optimizes therapy in patients with
6875:
4399:"Phase I, Dose-Escalating Study of the Safety and Pharmacokinetics of Inhaled Dry-Powder Vancomycin (AeroVanc) in Volunteers and Patients with Cystic Fibrosis: a New Approach to Therapy for Methicillin-Resistant Staphylococcus aureus"
3853:
Zhang M, Huang L, Zhu Y, Zeng L, Jia ZJ, Cheng G, et al. (January 2024). "Epidemiology of
Vancomycin in Combination With Piperacillin/Tazobactam-Associated Acute Kidney Injury in Children: A Systematic Review and Meta-analysis".
2029:(2003), the widespread use of vancomycin makes resistance to the drug a significant worry, especially for individual patients if resistant infections are not quickly identified and the patient continues the ineffective treatment.
1920:
In the resistant bacteria, cross-links are successfully formed; still, in the nonresistant (sensitive) bacteria, the vancomycin bound to the peptide chains prevents them from interacting properly with the cell wall cross-linking
1898:
Mechanism of vancomycin action and resistance: This diagram shows only one of two ways vancomycin acts against bacteria (inhibition of cell wall cross-linking) and only one of many ways that bacteria can become resistant to it.
3613:"Vancomycin therapeutic guidelines: a summary of consensus recommendations from the infectious diseases Society of America, the American Society of Health-System Pharmacists, and the Society of Infectious Diseases Pharmacists"
1667:
contain 3 epimerization domains. The origin of D-Leu at residue 1 is not known. The three peptide syntheses are located at the start of the region of the bacterial genome linked with antibiotic biosynthesis, and span 27 kb.
4536:
1368:
been often clinically referred to as "red man syndrome". The reaction usually appears within 4 to 10 min after the commencement or soon after the completion of an infusion and is characterized by flushing and/or an
1198:
thrombophlebitis, which is common when administered through peripheral catheters but not when central venous catheters are used, although central venous catheters are a predisposing factor for upper-extremity deep-vein
2118:
Variant of vancomycin has been tested that binds to the resistant D-lactic acid variation in vancomycin-resistant bacterial cell walls, and also binds well to the original target (vancomycin-susceptible bacteria).
4488:
3064:"Safety Alerts for Human Medical Products - Intraocular Injections of a Compounded Triamcinolone, Moxifloxacin, and Vancomycin (TMV) Formulation: FDA Statement - Case of Hemorrhagic Occlusive Retinal Vasculitis"
6364:
Bager F, Madsen M, Christensen J, Aarestrup FM (July 1997). "Avoparcin used as a growth promoter is associated with the occurrence of vancomycin-resistant
Enterococcus faecium on Danish poultry and pig farms".
2431:
4537:"Is there literature describing the efficacy or safety of inhaled vancomycin to treat MRSA ventilator-associated tracheobronchitis? | Drug Information Group | University of Illinois Chicago"
2092:
In enterococci, this modification appears to be due to the expression of an enzyme that alters the terminal residue. Three main resistance variants have been characterised to date among resistant
330:
1499:
of the target organism. Thus, peak serum levels have not been shown to correlate with efficacy or toxicity; indeed, concentration monitoring is unnecessary in most cases. Circumstances in which
2913:
Bruniera FR, Ferreira FM, Saviolli LR, Bacci MR, Feder D, da Luz Gonçalves
Pedreira M, et al. (February 2015). "The use of vancomycin with its therapeutic and adverse effects: a review".
3712:
Fuchs TC, Frick K, Emde B, Czasch S, von
Landenberg F, Hewitt P (2012). "Evaluation of novel acute urinary rat kidney toxicity biomarker for subacute toxicity studies in preclinical trials".
1211:) were side effects of the early impure versions of vancomycin, and these were prominent in the clinical trials conducted in the mid-1950s. Later trials using purer forms of vancomycin found
1313:
The mechanisms that underlie the pathogenesis of vancomycin nephrotoxicity are multifactorial but include interstitial nephritis, tubular injury due to oxidative stress, and cast formation.
4280:
Van
Bambeke F (August 2006). "Glycopeptides and glycodepsipeptides in clinical development: a comparative review of their antibacterial spectrum, pharmacokinetics and clinical efficacy".
1319:
can be used during vancomycin therapy to minimize the risk of nephrotoxicity associated with excessive drug exposure. Immunoassays are commonly utilized for measuring vancomycin levels.
2811:
Mühlberg E, Umstätter F, Kleist C, Domhan C, Mier W, Uhl P (January 2020). "Renaissance of vancomycin: approaches for breaking antibiotic resistance in multidrug-resistant bacteria".
198:
7865:
3071:
2000:
Most Gram-negative bacteria are intrinsically resistant to vancomycin because their outer membranes are impermeable to large glycopeptide molecules (with the exception of some non-
988:. The World Health Organization classifies vancomycin as critically important for human medicine. It is available as a generic medication. Vancomycin is made by the soil bacterium
1263:
265:
1709:. The target was first achieved by David Evans in October 1998, KC Nicolaou in December 1998, Dale Boger in 1999, and more selectively synthesized again by Dale Boger in 2020.
1902:
Vancomycin is added to the bacterial environment while it is trying to synthesize new cell wall. Here, the cell wall strands have been synthesized, but not yet cross-linked.
1835:
1616:-tyrosine is modified to become the β-hydroxytyrosine (β-HT) and 4-hydroxyphenylglycine (4-Hpg) residues. 3,5 dihydroxyphenylglycine ring (3,5-DPG) is derived from acetate.
846:
C1((C(O1)O2(((O2Oc3c4cc5cc3Oc6ccc(cc6Cl)((C(=O)N(C(=O)N5C(=O)N7c8ccc(c(c8)-c9c(cc(cc9O)O)(NC(=O)((c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)(CC(C)C)NC)O)CO)O)O)(C)N)O
1310:
kidney injury molecule-1 (KIM-1), clusterin, and osteopontin (OPN), and in humans, insulin-like growth factor binding protein 7 (IGFBP7) as part of the nephrocheck test.
7840:
4481:
1372:
rash that affects the face, neck, and upper torso, attributed to the release of histamine from mast cells. This reaction is caused by the interaction of vancomycin with
1106:
by intravitreal injection for Gram-positive bacteria coverage; it has been used to prevent the condition, however, is not recommended due to the risk of side effects.
5827:
Pazuki A, Asghari J, Sohani MM, Pessarakli M, Aflaki F (2014). "Effects of Some
Organic Nitrogen Sources and Antibiotics on Callus Growth of Indica Rice Cultivars".
2418:
2143:. In comparison to the unmodified vancomycin the activity against vancomycin-resistant bacteria could be enhanced by a factor of 1,000. This pharmacon is still in
7490:
4237:
Cafaro A, Stella M, Mesini A, Castagnola E, Cangemi G, Mattioli F, et al. (March 2024). "Dose optimization and target attainment of vancomycin in children".
1433:(IV) for systemic therapy, since it is poorly absorbed from the intestine. It is a large hydrophilic molecule that partitions poorly across the gastrointestinal
4866:
Samel SA, Marahiel MA, Essen LO (May 2008). "How to tailor non-ribosomal peptide products--new clues about the structures and mechanisms of modifying enzymes".
2057:
One mechanism of resistance to vancomycin involves the alteration to the terminal amino acid residues of the NAM/NAG-peptide subunits, under normal conditions,
1936:
Vancomycin is one of the few antibiotics used in plant tissue culture to eliminate Gram-positive bacterial infection. It has relatively low toxicity to plants.
113:
1740:
Vancomycin targets bacterial cell wall synthesis by binding to the basic building block of the bacterial cell wall of Gram-positive bacteria, whether it is of
6560:"A redesigned vancomycin engineered for dual D-Ala-D-ala And D-Ala-D-Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteria"
7850:
2980:"Recommendations for preventing the spread of vancomycin resistance. Recommendations of the Hospital Infection Control Practices Advisory Committee (HICPAC)"
838:
1882:-acetylglucosamine (NAG) that form the backbone strands of the bacterial cell wall, and prevents the backbone polymers from cross-linking with each other.
933:
2044:
2037:
2021:
to vancomycin is a growing problem, in particular, within healthcare facilities such as hospitals. While newer alternatives to vancomycin exist, such as
1511:, patients administered high-dose or prolonged treatment, and patients with impaired renal function. In such cases, trough concentrations are measured.
5632:"Different modes of vancomycin and D-alanyl-D-alanine peptidase binding to cell wall peptide and a possible role for the vancomycin resistance protein"
3483:
Blumenthal KG, Patil SU, Long AA (1 April 2012). "The importance of vancomycin in drug rash with eosinophilia and systemic symptoms (DRESS) syndrome".
2262:
The combination of vancomycin powder and povidone-iodine lavage may reduce the risk of periprosthetic joint infection in hip and knee arthroplasties.
3665:"Vancomycin-Induced Kidney Injury: Animal Models of Toxicodynamics, Mechanisms of Injury, Human Translation, and Potential Strategies for Prevention"
2234:
had expired in the early 1980s, and the FDA authorized the sale of several generic versions in the US, including from manufacturers
Bioniche Pharma,
164:
6494:
2081:-alanine) possible between vancomycin and the peptide. This loss of just one point of interaction results in a 1000-fold decrease in affinity. The
4446:
Falagas ME, Trigkidis KK, Vardakas KZ (March 2015). "Inhaled antibiotics beyond aminoglycosides, polymyxins and aztreonam: A systematic review".
1924:
In the resistant bacteria, stable cross-links are formed. In the sensitive bacteria, cross-links cannot be formed and the cell wall falls apart.
1608:
determine the amino acid sequence during its assembly through its 7 modules. Before vancomycin is assembled through NRPS, the non-proteinogenic
5803:
5511:
7434:
6758:
6125:
5482:
5442:
5425:
4910:
4648:
Karam CM, McKinnon PS, Neuhauser MM, Rybak MJ (March 1999). "Outcome assessment of minimizing vancomycin monitoring and dosing adjustments".
2786:
2750:
2556:
1517:
Target ranges for serum vancomycin concentrations have changed over the years. Early authors suggested peak levels of 30 to 40 mg/L and
985:
1673:
After the linear heptapeptide molecule is synthesized, vancomycin has to undergo further modifications, such as oxidative cross-linking and
6809:
2580:
1353:
vancomycin is added to nephrotoxins such as aminoglycosides. However, a dose- or serum level-effect relationship has not been established.
3063:
2999:
2299:
5003:
5200:
1495:
considered to be time-dependent; that is, antimicrobial activity depends on the duration that the serum drug concentration exceeds the
7483:
3097:
1681:-methylates the terminal leucine residue. GtfE then joins D-glucose to the phenolic oxygen of residue 4, followed by the addition of
7845:
5294:
Fu X, Albermann C, Jiang J, Liao J, Zhang C, Thorson JS (December 2003). "Antibiotic optimization via in vitro glycorandomization".
4166:
2956:
2030:
1853:
1339:
vancomycin serum level exceeded 80 μg/mL, cases have been reported in patients with therapeutic levels, as well. Thus, whether
1167:
dysgeusia (distorted sense of taste), in case of administration of vancomycin oral solution, but not in case of vancomycin capsules.
858:
194:
5465:
Herzner H, Rück-Braun K (2008). "38. Crossing the Finishing Line: Total Syntheses of the Vancomycin Aglycon". In Schmalz HG (ed.).
3178:"Therapeutic drug monitoring of glycopeptide antimicrobials: An overview of liquid chromatography-tandem mass spectrometry methods"
6207:
5781:
1717:
5119:"Biosynthesis of chloro-beta-hydroxytyrosine, a nonproteinogenic amino acid of the peptidic backbone of glycopeptide antibiotics"
2337:
1496:
1124:
3315:
2598:
1067:
treatment of infections caused by Gram-positive microorganisms in patients with serious allergies to beta-lactam antimicrobials,
6867:
1601:
456:
315:
145:
6733:
2181:
vancomycin. The rapid development of penicillin resistance by staphylococci led to its being fast-tracked for approval by the
1639:
bond formation at the contact sites of the activating domains. Each module typically consists of an adenylation (A) domain, a
3228:
Cantú TG, Yamanaka-Yuen NA, Lietman PS (April 1994). "Serum vancomycin concentrations: reappraisal of their clinical value".
2367:
2128:
1895:
1096:
6235:"Emergence of vancomycin resistance in Staphylococcus aureus. Glycopeptide-Intermediate Staphylococcus aureus Working Group"
1571:
owing to the rotational restriction of some of the bonds. The form present in the drug is the thermodynamically more stable
4196:
3147:
1025:
Hospital Infection Control Practices Advisory Committee. These guidelines restrict use of vancomycin to these indications:
7476:
5374:"Natural product disaccharide engineering through tandem glycosyltransferase catalysis reversibility and neoglycosylation"
4974:"An active serine is involved in covalent substrate amino acid binding at each reaction center of gramicidin S synthetase"
4217:
2947:
2477:
944:
7810:
5272:
3339:"Extensive thrombophlebitis with gas associated with continuous infusion of vancomycin through a central venous catheter"
2089:-serine variation causes a six-fold loss of affinity between vancomycin and the peptide, likely due to steric hindrance.
2036:
emerged in 1986. Vancomycin resistance evolved in more common pathogenic organisms during the 1990s and 2000s, including
2182:
1981:
1418:
613:
5608:
2501:"Clinical practice guidelines by the infectious diseases society of america for the treatment of methicillin-resistant
7451:
2111:
VanB - lower-level enterococcal resistance; inducible by vancomycin, but strains may remain susceptible to teicoplanin
1500:
1340:
1316:
1290:
1022:
701:
181:
5066:
Kohli RM, Walsh CT, Burkart MD (August 2002). "Biomimetic synthesis and optimization of cyclic peptide antibiotics".
4803:
3806:"Kinetics of Urinary Cell Cycle Arrest Markers for Acute Kidney Injury Following Exposure to Potential Renal Insults"
1289:
reassessed. With the removal of impurities present in earlier formulations of the drug, and with the introduction of
3757:"Comparative performance of urinary biomarkers for vancomycin-induced kidney injury according to timeline of injury"
2054:, another similar glycopeptide antibiotic, may have contributed to the evolution of vancomycin-resistant organisms.
1651:
to another, and a thioesterase domain (TE) is used as a catalyst for cyclization and releases of the molecule via a
969:
occur. Safety in pregnancy is not clear, but no evidence of harm has been found, and it is likely safe for use when
7299:
3268:"Relationship between initial vancomycin concentration-time profile and nephrotoxicity among hospitalized patients"
1227:
1160:
Common side effects associated with oral vancomycin administration (used to treat intestinal infections) include:
1042:
2728:
2700:
2672:
2426:
1975:
1969:
1527:
1503:
is warranted include: patients receiving concomitant aminoglycoside therapy, patients with (potentially) altered
159:
6456:"Effect of banning vancomycin analogue avoparcin on vancomycin-resistant enterococci in chicken farms in Taiwan"
2218:
and to the kidneys; these findings led to vancomycin's being relegated to the position of a drug of last resort.
7860:
6928:
2169:
2018:
1585:
1572:
1053:
1030:
990:
7210:
5337:
Fu X, Albermann C, Zhang C, Thorson JS (April 2005). "Diversifying vancomycin via chemoenzymatic strategies".
4613:
Moellering RC (April 1994). "Monitoring serum vancomycin levels: climbing the mountain because it is there?".
4513:
Palmer LB, Smaldone GC (2017). "Eradication of MRSA ventilator-associated infection with inhaled vancomycin".
1640:
6617:
NH]Tpg]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics"
4931:
van Wageningen AM, Kirkpatrick PN, Williams DH, Harris BR, Kershaw JK, Lennard NJ, et al. (March 1998).
7516:
7439:
7373:
5498:
Nicolaou KC, Mitchell HJ, Jain NF, Winssinger N, Hughes R, Bando T (1999). "Total Synthesis of Vancomycin".
2144:
1323:
1120:
974:
966:
897:
258:
235:
2214:
Early trials used early, impure forms of the drug ("Mississippi mud"), which were found to be toxic to the
740:
7772:
7244:
7219:
7016:
5867:"Antimicrobial susceptibility of vancomycin-resistant Leuconostoc, Pediococcus, and Lactobacillus species"
4774:"Development and evaluation of vancomycin dosage guidelines designed to achieve new target concentrations"
4728:
2303:
1064:
treatment (for this indication, vancomycin is given orally, rather than by its typical intravenous route),
6411:(August 1999). "Vancomycin-resistant enterococci and use of avoparcin in animal feed: is there a link?".
2390:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
690:
7855:
7395:
7131:
7027:
7022:
6455:
5730:"Neisseria gonorrhoeae strains inhibited by vancomycin in selective media and correlation with auxotype"
2160:
2001:
1808:-alanine moieties of the NAM/NAG-peptides. Under normal circumstances, this is a five-point interaction.
1482:
1448:
1181:
5168:"Bis-chlorination of a hexapeptide-PCP conjugate by the halogenase involved in vancomycin biosynthesis"
39:
1619:
7147:
6628:
6470:
6274:
McDonald LC, Killgore GE, Thompson A, Owens RC, Kazakova SV, Sambol SP, et al. (December 2005).
6233:
Smith TL, Pearson ML, Wilcox KR, Cruz C, Lancaster MV, Robinson-Dunn B, et al. (February 1999).
5240:
5075:
5027:"The multiple carrier model of nonribosomal peptide biosynthesis at modular multienzymatic templates"
3906:
2389:
1993:
1545:
1521:
of 5 to 10 mg/L, but current recommendations are that peak levels need not be measured and that
1215:
is an infrequent adverse effect (0.1% to 1% of patients), but this is accentuated in the presence of
909:
417:
4309:"Effect of vancomycin on intestinal flora of patients who previously received antimicrobial therapy"
2131:(Germany) re-gained the antibacterial power of vancomycin by modifying the molecule with a cationic
2114:
VanC - least clinically important; enterococci resistant only to vancomycin; constitutive resistance
1979:, which are sensitive. Other Gram-positive bacteria with intrinsic resistance to vancomycin include
1764:-Ala) peptide motif of the peptidoglycan precursor, a crucial component of the bacterial cell wall.
562:
6986:
5810:
4733:
2307:
2073:-lactate variation results in the loss of one hydrogen-bonding interaction (4, as opposed to 5 for
1514:
Therapeutic drug monitoring is also used for dose optimization of vancomycin in treating children.
1231:
940:
901:
717:
505:
246:
7095:
6853:
6436:
6390:
6305:
6117:
6111:
5945:
5844:
5319:
5264:
5099:
4754:
4673:
4262:
3875:
3737:
3642:
2846:
2167:
by a missionary, William M. Bouw (1918–2006). The organism that produced it was eventually named
1745:
1690:
1222:
Rare adverse effects associated with intravenous (IV) vancomycin (<0.1% of patients) include:
1011:
962:
209:
6813:
6221:
faecalis, subsequently classified as VanB type, was recovered from patients in Missouri in 1987.
4933:"Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic"
123:
6325:"Avoparcin and virginiamycin as animal growth promoters: a plea for science in decision-making"
6063:
Kumar A, Augustine D, Sudhindran S, Kurian AM, Dinesh KR, Karim S, et al. (October 2011).
4973:
4972:
Schlumbohm W, Stein T, Ullrich C, Vater J, Krause M, Marahiel MA, et al. (December 1991).
4562:
Zarogoulidis P, Kioumis I, Lampaki S, Organtzis J, Porpodis K, Spyratos D, et al. (2014).
3518:
Von Drygalski A, Curtis BR, Bougie DW, McFarland JG, Ahl S, Limbu I, et al. (March 2007).
2979:
1092:
for possible MRSA infection while waiting for culture identification of the infecting organism,
6905:
6845:
6791:
6754:
6705:
6656:
6589:
6536:
6532:
6486:
6428:
6382:
6346:
6297:
6256:
6199:
6158:
6121:
6086:
6045:
5996:
5937:
5896:
5759:
5710:
5661:
5600:
5548:
5478:
5447:
5403:
5354:
5311:
5256:
5192:
5148:
5091:
5048:
4995:
4954:
4906:
4883:
4848:
4795:
4746:
4700:
4665:
4630:
4595:
4463:
4428:
4379:
4330:
4289:
4254:
4188:
4162:
4139:
4088:
4039:
3985:
3934:
3867:
3835:
3786:
3729:
3694:
3634:
3593:
3541:
3500:
3465:
3416:
3368:
3289:
3245:
3207:
3139:
3044:
2991:
2952:
2922:
2895:
2838:
2782:
2746:
2654:
2552:
2526:
2235:
1326:
has been associated with an elevated incidence of AKI, relative to other antibiotic regimens.
954:
670:
354:
342:
103:
7520:
7366:
7316:
6837:
6783:
6695:
6687:
6674:
Umstätter F, Domhan C, Hertlein T, Ohlsen K, Mühlberg E, Kleist C, et al. (June 2020).
6646:
6636:
6579:
6571:
6528:
6478:
6420:
6374:
6336:
6287:
6246:
6191:
6150:
6076:
6035:
6027:
5986:
5976:
5927:
5886:
5878:
5836:
5749:
5741:
5700:
5692:
5651:
5643:
5590:
5582:
5538:
5507:
5470:
5437:
5393:
5385:
5346:
5303:
5248:
5182:
5138:
5130:
5083:
5038:
4985:
4944:
4875:
4838:
4785:
4738:
4657:
4622:
4585:
4575:
4518:
4455:
4418:
4410:
4369:
4361:
4320:
4246:
4129:
4119:
4078:
4070:
4029:
4019:
3975:
3965:
3924:
3914:
3859:
3825:
3817:
3776:
3768:
3721:
3684:
3676:
3624:
3583:
3575:
3531:
3492:
3455:
3447:
3406:
3358:
3350:
3279:
3237:
3197:
3189:
3034:
3026:
2885:
2877:
2828:
2820:
2774:
2736:
2708:
2680:
2644:
2516:
2227:
2185:. In 1958, Eli Lilly first marketed vancomycin hydrochloride under the trade name Vancocin.
1741:
1658:
1504:
1270:
1239:
1075:
1007:
757:
389:
57:
6726:, Mier W, Umstätter F, Uhl P, Domhan C, "Improved polypeptide coupled antibiotics."
5228:"X-domain of peptide synthetases recruits oxygenases crucial for glycopeptide biosynthesis"
5167:
4348:
Peláez T, Alcalá L, Alonso R, Rodríguez-Créixems M, García-Lechuz JM, Bouza E (June 2002).
2499:
Liu C, Bayer A, Cosgrove SE, Daum RS, Fridkin SK, Gorwitz RJ, et al. (February 2011).
2196:
It possesses poor oral bioavailability, so must be given intravenously for most infections.
622:
602:
7824:
7390:
7326:
6787:
6737:
6408:
6154:
5679:
Crew PE, McNamara L, Waldron PE, McCulley L, Jones SC, Bersoff-Matcha SJ (February 2019).
5117:
Puk O, Bischoff D, Kittel C, Pelzer S, Weist S, Stegmann E, et al. (September 2004).
5025:
Stein T, Vater J, Kruft V, Otto A, Wittmann-Liebold B, Franke P, et al. (June 1996).
4221:
3176:
Cafaro A, Barco S, Pigliasco F, Russo C, Mariani M, Mesini A, et al. (January 2024).
3093:
2284:
2156:
1706:
1648:
1389:
1177:
looking at trough values. Immunoassays are commonly used to measure levels of vancomycin.
1103:
1089:
514:
407:
397:
4825:
Izumisawa T, Kaneko T, Soma M, Imai M, Wakui N, Hasegawa H, et al. (December 2019).
4522:
4187:, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012,
2211:) were subsequently developed, which have better activity against non-MRSA staphylococci.
1909:-ala residues on the end of the peptide chains. However, in resistant bacteria, the last
6632:
6474:
6424:
5244:
5079:
3910:
3202:
3177:
2279:
744:
721:
7711:
7468:
7445:
7262:
7167:
7101:
7032:
6951:
6909:
6898:
6700:
6675:
6651:
6612:
6584:
6559:
6454:
Lauderdale TL, Shiau YR, Wang HY, Lai JF, Huang IW, Chen PC, et al. (March 2007).
6178:
6106:
5991:
5964:
5705:
5680:
5595:
5398:
5373:
4590:
4563:
4423:
4398:
4083:
4058:
3980:
3953:
3929:
3894:
3830:
3805:
3781:
3756:
3689:
3664:
3363:
3338:
3094:"Vancomycin (Vancocyn, Lyphocin) | the Antimicrobial Index Knowledgebase - TOKU-E"
3039:
3014:
2890:
2865:
2778:
2247:
2173:. The original indication for vancomycin was for the treatment of penicillin-resistant
1628:
1549:
1235:
1216:
1212:
1204:
939:. Blood levels may be measured to determine the correct dose. Vancomycin is also taken
917:
6378:
6040:
6015:
5891:
5866:
5754:
5729:
5656:
5631:
5143:
5118:
4990:
4949:
4932:
4459:
4374:
4350:"Reassessment of Clostridium difficile susceptibility to metronidazole and vancomycin"
4349:
4250:
4134:
4107:
4034:
4007:
3588:
3563:
3460:
3435:
2594:
2329:
7834:
7787:
7767:
7716:
7644:
7624:
7332:
7284:
7215:
6945:
6857:
6608:
6555:
6482:
6341:
6324:
6031:
5949:
5932:
5915:
5134:
4564:"Optimization of nebulized delivery of linezolid, daptomycin, and vancomycin aerosol"
4266:
3879:
3564:"Retrospective study of the toxicity of preparations of vancomycin from 1974 to 1981"
3436:"Retrospective study of the toxicity of preparations of vancomycin from 1974 to 1981"
3307:
2850:
1963:
1797:
1734:
1674:
1644:
1542:
1522:
1518:
1414:
1385:
1269:
Vancomycin can induce platelet-reactive antibodies in the patient, leading to severe
1099:
and preventing symptoms; vancomycin does not cure the patient and success is limited,
1061:
1003:
1002:
Vancomycin is indicated for the treatment of serious, life-threatening infections by
970:
905:
733:
367:
137:
6440:
6309:
6016:"Mechanism of intrinsic resistance to vancomycin in Clostridium innocuum NCIB 10674"
5848:
5527:"Biography of Professor Nicolaou: a journey to the extremes of molecular complexity"
4758:
4677:
4365:
3741:
3646:
1468:, for the treatment of various infections of the upper and lower respiratory tract.
1192:
7696:
7691:
7605:
7507:
7503:
7415:
7309:
7269:
7152:
7048:
7001:
6913:
6723:
6394:
6065:"Weissella confusa: a rare cause of vancomycin-resistant Gram-positive bacteraemia"
5323:
5268:
5103:
3663:
Pais GM, Liu J, Zepcan S, Avedissian SN, Rhodes NJ, Downes KJ, et al. (2020).
2572:
2132:
1652:
1508:
1369:
1362:
1071:
1018:
984:
Vancomycin was approved for medical use in the United States in 1958. It is on the
958:
925:
298:
293:
288:
283:
278:
273:
2359:
1733:-Ala (bacterial cell wall precursor, in green) bound to vancomycin (blue) through
1592:
539:
5840:
5681:"Unusual Neisseria species as a cause of infection in patients taking eculizumab"
5424:
Evans DA, Wood MR, Trotter BW, Richardson TI, Barrow JC, Katz JL (October 1998).
4074:
3919:
3821:
3193:
7777:
7752:
7701:
7662:
7586:
7553:
7543:
7538:
7499:
7347:
7235:
7157:
6991:
6961:
6251:
6234:
6195:
6014:
David V, Bozdogan B, Mainardi JL, Legrand R, Gutmann L, Leclercq R (June 2004).
5745:
5443:
10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P
4661:
3131:
2473:
2208:
2200:
2105:
1957:
1951:
1793:
1682:
1609:
1564:
1430:
1377:
1335:
1259:
1243:
1223:
1208:
242:
131:
6621:
Proceedings of the National Academy of Sciences of the United States of America
5696:
5512:
10.1002/(SICI)1521-3773(19990115)38:1/2<240::AID-ANIE240>3.0.CO;2-5
5474:
4626:
4214:
4182:
3241:
1705:
and the complete vancomycin molecule have been targets successfully reached by
1306:
mainly associations studies where the cause of AKI is usually multifacotorial.
1060:; in particular, in cases of relapse or where the infection is unresponsive to
7782:
7747:
7742:
7732:
7682:
7672:
7634:
7629:
7558:
7548:
7533:
7420:
7410:
7405:
7342:
7337:
7294:
7289:
7279:
7240:
7069:
7042:
6902:
6841:
6810:"Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations"
6141:
Geraci JE, Wilson WR (1981). "Vancomycin therapy for infective endocarditis".
3970:
3863:
2223:
2026:
1967:
species are also intrinsically resistant to vancomycin, with the exception of
1662:
Figure 3: Modifications necessary for vancomycin to become biologically active
1539:
1381:
1278:
1247:
1082:
929:
796:
593:
253:
5227:
5043:
5026:
3725:
3496:
2705:
World Health Organization model list of essential medicines: 22nd list (2021)
2300:"vancomycin - definition of vancomycin in English from the Oxford dictionary"
1376:, a GPCR mediating IgE-independent mast cell degranulation. Less frequently,
7792:
7762:
7757:
7737:
7706:
7657:
7615:
7573:
7528:
7225:
7200:
7142:
7114:
7085:
7079:
7063:
7053:
6996:
6971:
6966:
6641:
6519:
Pootoolal J, Neu J, Wright GD (2002). "Glycopeptide antibiotic resistance".
5567:
4827:"Augmented Renal Clearance of Vancomycin in Hematologic Malignancy Patients"
3354:
2215:
2204:
2051:
2022:
2005:
1987:
1785:
1477:
1465:
1461:
1255:
978:
438:
117:
6849:
6709:
6691:
6676:"Vancomycin Resistance Is Overcome by Conjugation of Polycationic Peptides"
6660:
6593:
6540:
6490:
6432:
6350:
6301:
6260:
6203:
6090:
6081:
6064:
6049:
6000:
5916:"Vancomycin susceptibility as an aid to the identification of lactobacilli"
5714:
5604:
5552:
5451:
5407:
5358:
5315:
5260:
5196:
5152:
5095:
4887:
4852:
4799:
4750:
4669:
4599:
4467:
4432:
4383:
4293:
4258:
4192:
4143:
4092:
4043:
3989:
3938:
3871:
3839:
3790:
3733:
3698:
3638:
3545:
3504:
3420:
3372:
3293:
3211:
3143:
3048:
2926:
2899:
2842:
2677:
World Health Organization model list of essential medicines: 21st list 2019
2658:
2530:
1049:
treatment of infections in individuals with serious allergy to penicillins,
22:
6795:
6386:
6162:
5981:
5941:
5900:
5763:
5665:
5647:
5372:
Peltier-Pain P, Marchillo K, Zhou M, Andes DR, Thorson JS (October 2012).
5052:
4999:
4958:
4843:
4826:
4773:
4634:
4334:
3597:
3469:
3249:
3030:
2995:
2824:
2163:) from a bacteria in a soil sample collected from the interior jungles of
7797:
7667:
7652:
7581:
7274:
7195:
7184:
7180:
7122:
6981:
6976:
6956:
6292:
6275:
5882:
5586:
4790:
4704:
4414:
3772:
3579:
3536:
3519:
3451:
2773:. Studies in Natural Products Chemistry. Vol. 50. pp. 249–297.
2521:
2500:
1702:
1274:
1251:
573:
176:
5543:
5526:
5252:
5087:
4580:
3266:
Lodise TP, Patel N, Lomaestro BM, Rodvold KA, Drusano GL (August 2009).
3015:"Vancomycin and ceftazidime incompatibility upon intravitreal injection"
2741:
2713:
2685:
1949:
A few Gram-positive bacteria are intrinsically resistant to vancomycin:
1623:
Figure 2: Linear heptapeptide, which consists of modified aromatic rings
582:
7596:
7190:
7127:
5225:
Haslinger K, Peschke M, Brieke C, Maximowitsch E, Cryle MJ (May 2015).
5187:
4742:
4209:
2251:
2136:
1632:
1605:
1568:
1373:
1282:
1184:(≥1% of patients) associated with intravenous (IV) vancomycin include:
525:
30:
6575:
5965:"Erysipelothrix rhusiopathiae endocarditis and presumed osteomyelitis"
5389:
5350:
4059:"Brief communication: MRGPRX2, atopic dermatitis and red man syndrome"
3680:
3013:
Lifshitz T, Lapid-Gortzak R, Finkelman Y, Klemperer I (January 2000).
2833:
7171:
7137:
6323:
Acar J, Casewell M, Freeman J, Friis C, Goossens H (September 2000).
4879:
4307:
Edlund C, Barkholt L, Olsson-Liljequist B, Nord CE (September 1997).
2881:
2239:
2231:
2164:
1434:
1164:
gastrointestinal adverse effects (such as abdominal pain and nausea);
1116:
921:
681:
6110:. In Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken RH (eds.).
1771:
Vancomycin inhibits bacterial cell wall synthesis by binding to the
1081:
surgical prophylaxis for major procedures involving implantation of
5566:
Moore MJ, Qu S, Tan C, Cai Y, Mogi Y, Keith DJ, et al. (202).
5307:
4325:
4308:
4124:
4024:
3629:
3612:
3411:
3394:
3284:
3267:
2649:
2632:
1961:
species, but these organisms rarely cause diseases in humans. Most
650:
642:
7400:
2243:
1716:
1657:
1636:
1618:
1591:
1127:
susceptibility data for a few medically significant bacteria are:
1123:, skin, and bone infections caused by Gram-positive bacteria. The
823:
814:
661:
6276:"An epidemic, toxin gene-variant strain of Clostridium difficile"
4772:
Thomson AH, Staatz CE, Tobin CM, Gall M, Lovering AM (May 2009).
5166:
Schmartz PC, Zerbe K, Abou-Hadeed K, Robinson JA (August 2014).
4006:
Launay-Vacher V, Izzedine H, Mercadal L, Deray G (August 2002).
1034:
1029:
treatment of serious infections caused by susceptible organisms
913:
633:
376:
348:
154:
7472:
6871:
1140:(methicillin resistant or MRSA): 1 μg/mL to 138 μg/mL
361:
188:
171:
163:
6751:
The Killers Within: The Deadly Rise of Drug-Resistant Bacteria
4008:"Clinical review: use of vancomycin in haemodialysis patients"
2397:
1810:
1322:
In children, the concomitant administration of vancomycin and
953:
Common side effects include pain in the area of injection and
4397:
Waterer G, Lord J, Hofmann T, Jouhikainen T (February 2020).
4213:
Text was copied from this source, which is available under a
1783:
Gram-positive bacteria (except some nongonococcal species of
1748:
type. Specifically, vancomycin forms hydrogen bonds with the
1021:
has resulted in the development of guidelines for use by the
2735:(6th revision ed.). Geneva: World Health Organization.
1437:. Due to short half-life, it is often injected twice daily.
1115:
Vancomycin is a last resort medication for the treatment of
706:
3611:
Rybak MJ, Lomaestro BM, Rotschafer JC, et al. (2009).
324:
220:
81:
72:
66:
2549:
Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition
1874:-Ala prevents cell wall synthesis of the long polymers of
1384:
may also occur. Symptoms may be treated or prevented with
5469:. Vol. IV. John Wiley & Sons. pp. 281–288.
3755:
Pais GM, Avedissian SN, ODonnell JN, et al. (2019).
87:
63:
2689:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
2199:β-Lactamase-resistant semisynthetic penicillins such as
1191:
vancomycin flushing syndrome (VFS), previously known as
337:
5426:"Total Syntheses of Vancomycin and Eremomycin Aglycons"
1831:
1627:
Nonribosomal peptide synthesis occurs through distinct
1452:
have a mean inhibitory concentration of ≤2 μg/mL)
986:
World Health Organization's List of Essential Medicines
883:
4215:
Creative Commons Attribution 4.0 International License
3895:"Long-term vancomycin use had low risk of ototoxicity"
2733:
Critically important antimicrobials for human medicine
7808:
2505:
infections in adults and children: executive summary"
2476:. The American Society of Health-System Pharmacists.
2188:
Vancomycin never became the first-line treatment for
1647:(E) domain, which isomerizes the amino acid from one
1357:
Vancomycin Flushing Reaction (aka "Red man syndrome")
90:
84:
69:
5865:
Swenson JM, Facklam RR, Thornsberry C (April 1990).
3308:"Vancomycin Injection: MedlinePlus Drug Information"
1596:
Figure 1: Modules and domains of vancomycin assembly
60:
7725:
7681:
7643:
7614:
7595:
7572:
7515:
7383:
7358:
7254:
7166:
7112:
6937:
6921:
6116:(6th ed.). Washington DC: ASM Press. pp.
4903:
Medicinal natural products: a biosynthetic approach
4159:
Andrews' Diseases of the Skin: Clinical Dermatology
1826:
may be too technical for most readers to understand
1600:Vancomycin biosynthesis occurs primarily via three
1392:, and are less likely to occur with slow infusion.
812:
795:
756:
751:
732:
700:
680:
660:
632:
612:
592:
572:
549:
524:
504:
447:
437:
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406:
396:
388:
314:
309:
264:
252:
234:
208:
144:
130:
112:
102:
78:
75:
51:
46:
6774:Griffith RS (1981). "Introduction to vancomycin".
6177:
6107:"Mechanisms of Resistance to Antimicrobial Agents"
6105:
5226:
3893:Humphrey C, Veve MP, Walker B, Shorman MA (2019).
3337:Leroy S, Piquet P, Chidiac C, Ferry T (May 2012).
2419:"List of nationally authorised medicinal products"
1334:Attempts to establish rates of vancomycin-induced
2104:VanA - enterococcal resistance to vancomycin and
1293:, the risk for severe toxicity has been reduced.
1188:pain, redness, or swelling at the injection site;
1085:in institutions with a high rate of MRSA or MRSE,
1017:The increasing emergence of vancomycin-resistant
3557:
3555:
561:
538:
5568:"Next-Generation Total Synthesis of Vancomycin"
5419:
5417:
4232:
4230:
4001:
3999:
3954:"Ototoxicity of Non-aminoglycoside Antibiotics"
3658:
3656:
3388:
3386:
3384:
3382:
3261:
3259:
3171:
3169:
3167:
3165:
3138:. Treasure Island (FL): StatPearls Publishing.
3125:
3123:
3121:
3119:
3117:
3115:
2866:"Molecular mechanisms of vancomycin resistance"
2806:
2804:
2802:
2800:
2798:
2626:
2624:
2622:
2620:
2618:
2616:
1421:for either intravenous or oral administration.
513:
6179:"Vancomycin-resistant enterococcal infections"
5963:Romney M, Cheung S, Montessori V (July 2001).
5860:
5858:
4926:
4924:
4922:
3223:
3221:
193:
7866:World Health Organization essential medicines
7484:
6883:
3804:Ostermann M, McCullough PA, Forni LG (2018).
2573:"Prescribing medicines in pregnancy database"
2551:. Jones & Bartlett Learning. p. 91.
8:
6521:Annual Review of Pharmacology and Toxicology
5914:Hamilton-Miller JM, Shah S (February 1998).
5728:Mirrett S, Reller LB, Knapp JS (July 1981).
3520:"Vancomycin-induced immune thrombocytopenia"
977:and works by blocking the construction of a
180:
21:
5969:The Canadian Journal of Infectious Diseases
4482:"Inhaled Vancomycin Monograph - Paediatric"
4161:(10th ed.). Saunders. pp. 120–1.
4057:Azimi E, Reddy VB, Lerner EA (March 2017).
2951:. Adelaide: Australian Medicines Handbook.
1905:Vancomycin recognizes and binds to the two
1074:following certain procedures in penicillin-
950:. When taken orally it is poorly absorbed.
7491:
7477:
7469:
6890:
6876:
6868:
6613:"Peripheral modifications of [Ψ[CH
4721:American Journal of Health-System Pharmacy
3952:Rybak LP, Ramkumar V, Mukherjea D (2021).
2940:
2938:
2936:
2769:Biondi S, Chugunova E, Panunzio M (2016).
2468:
2466:
2464:
2462:
2460:
2458:
2456:
2454:
2452:
2155:Vancomycin was first isolated in 1953, by
1014:types, unresponsive to other antibiotics.
743:
720:
601:
6699:
6650:
6640:
6583:
6533:10.1146/annurev.pharmtox.42.091601.142813
6340:
6291:
6250:
6080:
6039:
5990:
5980:
5931:
5890:
5753:
5704:
5655:
5594:
5542:
5441:
5397:
5186:
5142:
5042:
4989:
4948:
4842:
4789:
4778:The Journal of Antimicrobial Chemotherapy
4732:
4589:
4579:
4422:
4373:
4324:
4133:
4123:
4082:
4033:
4023:
3979:
3969:
3928:
3918:
3829:
3780:
3688:
3628:
3587:
3535:
3459:
3434:Farber BF, Moellering RC (January 1983).
3410:
3362:
3283:
3201:
3038:
2889:
2832:
2740:
2712:
2684:
2648:
2542:
2540:
2520:
2226:in the U.S., Flynn Pharma in the UK, and
2065:-alanine, to which vancomycin binds. The
1854:Learn how and when to remove this message
1838:, without removing the technical details.
1635:by one amino acid per module through the
1583:Vancomycin is made by the soil bacterium
621:
7841:Drugs developed by Eli Lilly and Company
6564:Journal of the American Chemical Society
4831:Biological & Pharmaceutical Bulletin
4691:Geraci JE (October 1977). "Vancomycin".
4282:Current Opinion in Investigational Drugs
2222:In 2004, Eli Lilly licensed Vancocin to
7815:
3002:from the original on 23 September 2006.
2764:
2762:
2271:
2108:; inducible on exposure to these agents
1796:molecule of vancomycin is able to form
1480:use of vancomycin for the treatment of
863:
843:
716:
581:
461:
136:
6210:from the original on 11 September 2022
6104:Quintiliani Jr R, Courvalin P (1995).
4806:from the original on 15 September 2017
3130:Patel S, Preuss CV, Bernice F (2023).
2974:
2972:
2970:
2968:
2864:Stogios PJ, Savchenko A (March 2020).
2437:from the original on 25 September 2023
734:
20:
6554:Xie J, Pierce JG, James RC, Okano A,
5871:Antimicrobial Agents and Chemotherapy
5636:Antimicrobial Agents and Chemotherapy
5275:from the original on 24 February 2021
4354:Antimicrobial Agents and Chemotherapy
3440:Antimicrobial Agents and Chemotherapy
3100:from the original on 27 February 2014
2707:. Geneva: World Health Organization.
2679:. Geneva: World Health Organization.
2601:from the original on 7 September 2015
2480:from the original on 6 September 2015
2340:from the original on 24 December 2019
1836:make it understandable to non-experts
1721:Crystal structure of a short peptide
1567:—it has multiple chemically distinct
1146:: ≤0.12 μg/mL to 6.25 μg/mL
943:(by mouth) as a treatment for severe
900:medication used to treat a number of
689:
669:
122:
7:
5206:from the original on 2 February 2024
5175:Organic & Biomolecular Chemistry
4523:10.1183/1393003.congress-2017.OA4655
4157:James W, Berger T, Elston D (2005).
4106:Sivagnanam S, Deleu D (April 2003).
3562:Farber BF, Moellering RC Jr (1983).
3395:"Vancomycin: a 50-year reassessment"
3019:The British Journal of Ophthalmology
2595:"Vancomycin use while Breastfeeding"
1917:-lactate, so vancomycin cannot bind.
1913:-ala residue has been replaced by a
1460:Inhaled vancomycin can also be used
1348:Interactions with other nephrotoxins
552:
297:
287:
277:
7851:Halogen-containing natural products
7255:Intestinal anti-inflammatory agents
6788:10.1093/clinids/3.Supplement_2.S200
6425:10.5694/j.1326-5377.1999.tb123568.x
6329:Clinical Microbiology and Infection
6280:The New England Journal of Medicine
6239:The New England Journal of Medicine
6184:The New England Journal of Medicine
6155:10.1093/clinids/3.Supplement_2.S250
5031:The Journal of Biological Chemistry
4978:The Journal of Biological Chemistry
4487:. Perth Children's Hospital (PCH).
3524:The New England Journal of Medicine
3074:from the original on 3 October 2017
2135:. The oligopeptide consists of six
1134:: 0.25 μg/mL to 4.0 μg/mL
649:
641:
529:
5804:"vancomcin for plant cell culture"
4719:Infectious Diseases Pharmacists".
4494:from the original on 14 March 2023
3150:from the original on 11 April 2023
2779:10.1016/B978-0-444-63749-9.00008-6
2583:from the original on 8 April 2014.
1866:This binding of vancomycin to the
1604:(NRPSs) VpsA, VpsB, and VpsC. The
14:
7312:agents, excluding corticosteroids
5611:from the original on 13 July 2024
5006:from the original on 13 July 2024
4543:from the original on 19 July 2023
4460:10.1016/j.ijantimicag.2014.10.008
4251:10.1016/j.clinbiochem.2024.110728
3318:from the original on 19 July 2023
2984:MMWR. Recommendations and Reports
2360:"Vancomycin Use During Pregnancy"
928:, bone and joint infections, and
916:) as a treatment for complicated
432:(adults, impaired renal function)
7818:
6749:Shnayerson M, Plotkin M (2003).
6500:from the original on 10 May 2019
6483:10.1111/j.1462-2920.2006.01189.x
6413:The Medical Journal of Australia
6342:10.1046/j.1469-0691.2000.00128.x
6032:10.1128/JB.186.11.3415-3422.2004
5933:10.1046/j.1472-765X.1998.00297.x
5135:10.1128/JB.186.18.6093-6100.2004
4208:
4199:from the original on 14 May 2021
2370:from the original on 6 June 2019
1887:
1815:
1497:minimum inhibitory concentration
1417:, vancomycin is approved by the
1125:minimum inhibitory concentration
780:
774:
768:
56:
38:
29:
6113:Manual of Clinical Microbiology
6069:Journal of Medical Microbiology
5920:Letters in Applied Microbiology
5630:Knox JR, Pratt RF (July 1990).
4366:10.1128/AAC.46.6.1647-1650.2002
2990:(RR-12): 1–13. September 1995.
1800:interactions with the terminal
1040:(MRSA) and multidrug-resistant
871:Key:MYPYJXKWCTUITO-LYRMYLQWSA-N
427:(adults, normal renal function)
6776:Reviews of Infectious Diseases
6367:Preventive Veterinary Medicine
6143:Reviews of Infectious Diseases
5525:Winssinger N (February 2018).
3485:Allergy and Asthma Proceedings
3393:Moellering RC (January 2006).
2771:From Natural Products to Drugs
2285:Merriam-Webster.com Dictionary
2129:University Hospital Heidelberg
1878:-acetylmuramic acid (NAM) and
1602:nonribosomal protein syntheses
1097:primary sclerosing cholangitis
1070:antibacterial prophylaxis for
786:
762:
1:
7359:Antidiarrheal micro-organisms
6379:10.1016/S0167-5877(96)01119-1
4991:10.1016/S0021-9258(18)54473-2
4950:10.1016/S1074-5521(98)90060-6
2948:Australian Medicines Handbook
1631:that can load and extend the
5841:10.1080/01904167.2014.983118
5467:Organic Synthesis Highlights
4615:Clinical Infectious Diseases
4313:Clinical Infectious Diseases
4075:10.1097/itx.0000000000000005
3920:10.1371/journal.pone.0224561
3822:10.1097/CCM.0000000000002847
3399:Clinical Infectious Diseases
3272:Clinical Infectious Diseases
3230:Clinical Infectious Diseases
3194:10.1016/j.jmsacl.2023.12.003
3182:J Mass Spectrom Adv Clin Lab
3062:Office of the Commissioner.
2637:Clinical Infectious Diseases
2509:Clinical Infectious Diseases
2183:Food and Drug Administration
2050:(VRSA). Agricultural use of
1982:Erysipelothrix rhusiopathiae
1476:Rectal administration is an
1419:Food and Drug Administration
6252:10.1056/NEJM199902183400701
6196:10.1056/NEJM200003093421007
5746:10.1128/jcm.14.1.94-99.1981
4662:10.1592/phco.19.4.257.30933
4403:Antimicrob Agents Chemother
3761:Antimicrob Agents Chemother
3568:Antimicrob Agents Chemother
1501:therapeutic drug monitoring
1490:Therapeutic drug monitoring
1341:therapeutic drug monitoring
1317:Therapeutic drug monitoring
1291:therapeutic drug monitoring
1095:halting the progression of
1023:Centers for Disease Control
7882:
7201:Camphorated opium tincture
6938:Intestinal anti-infectives
6463:Environmental Microbiology
5829:Journal of Plant Nutrition
5697:10.1016/j.jinf.2018.10.015
5531:The Journal of Antibiotics
5475:10.1002/9783527619979.ch38
2717:. WHO/MHP/HPS/EML/2021.02.
2631:Levine DP (January 2006).
1360:
1228:toxic epidermal necrolysis
1172:Intravenous administration
1111:Spectrum of susceptibility
752:Chemical and physical data
7429:
6842:10.1016/j.jos.2022.11.013
3971:10.3389/fneur.2021.652674
3864:10.1177/10600280231220379
2915:Eur Rev Med Pharmacol Sci
2729:World Health Organization
2701:World Health Organization
2673:World Health Organization
2427:European Medicines Agency
1538:Vancomycin is a branched
1528:augmented renal clearance
1429:Vancomycin must be given
1273:and bleeding with florid
1088:early in treatment as an
1078:individuals at high risk,
879:
854:
834:
452:
37:
28:
7846:Glycopeptide antibiotics
7134:, known as Pepto-Bismol)
6929:Oral rehydration therapy
6176:Murray BE (March 2000).
5044:10.1074/jbc.271.26.15428
4627:10.1093/clinids/18.4.544
3726:10.1177/0192623312444618
3497:10.2500/aap.2012.33.3498
3242:10.1093/clinids/18.4.533
2170:Amycolatopsis orientalis
2038:vancomycin-intermediate
1641:peptidyl carrier protein
1586:Amycolatopsis orientalis
1554:Amycolatopsis orientalis
1507:parameters, patients on
1409:Routes of administration
1401:hours for 7 to 10 days.
1054:pseudomembranous colitis
1033:to penicillins, such as
991:Amycolatopsis orientalis
443:urine (IV), feces (oral)
7374:Saccharomyces boulardii
6642:10.1073/pnas.1704125114
6020:Journal of Bacteriology
5778:"Clinical Pharmacology"
5123:Journal of Bacteriology
4937:Chemistry & Biology
4693:Mayo Clinic Proceedings
4448:Int J Antimicrob Agents
4220:16 October 2017 at the
3355:10.1136/bcr-2012-006347
2633:"Vancomycin: a history"
2145:preclinical development
1612:are first synthesized.
1324:piperacillin/tazobactam
1203:Damage to the kidneys (
1195:(or "redman syndrome");
1121:lower respiratory tract
975:glycopeptide antibiotic
967:bone marrow suppression
898:glycopeptide antibiotic
259:Glycopeptide antibiotic
6736:8 October 2021 at the
6692:10.1002/anie.202002727
6082:10.1099/jmm.0.027169-0
4515:Respiratory Infections
2304:OxfordDictionaries.com
2127:In 2020 a team at the
2123:"Re-gained" vancomycin
1737:
1663:
1624:
1597:
1207:) and to the hearing (
1182:adverse drug reactions
1035:methicillin-resistant
934:methicillin-resistant
922:bloodstream infections
7396:Bismuth subsalicylate
7132:bismuth subsalicylate
7028:Succinylsulfathiazole
7023:Phthalylsulfathiazole
5648:10.1128/AAC.34.7.1342
4844:10.1248/bpb.b19-00652
4239:Clinical Biochemistry
3858:: 10600280231220379.
3031:10.1136/bjo.84.1.117a
2945:Rossi S, ed. (2006).
2825:10.1139/cjm-2019-0309
2577:Australian Government
2503:Staphylococcus aureus
2203:(and its successors,
2192:for several reasons:
2175:Staphylococcus aureus
2045:vancomycin-resistant
2031:Vancomycin-resistant
1940:Antibiotic resistance
1720:
1661:
1622:
1595:
1556:(formerly designated
1483:Clostridium difficile
1449:Clostridium difficile
1396:Dosing considerations
1275:petechial hemorrhages
946:Clostridium difficile
936:Staphylococcus aureus
16:Antibiotic medication
7726:Other antibacterials
7384:Other antidiarrheals
6293:10.1056/NEJMoa051590
6075:(Pt 10): 1539–1541.
5883:10.1128/AAC.34.4.543
5587:10.1021/jacs.0c07433
5500:Angew. Chem. Int. Ed
5296:Nature Biotechnology
4868:Molecular BioSystems
4415:10.1128/AAC.01776-19
3773:10.1128/AAC.00079-19
3580:10.1128/AAC.23.1.138
3537:10.1056/NEJMoa065066
3452:10.1128/AAC.23.1.138
2310:on 20 September 2013
2094:Enterococcus faecium
2019:microbial resistance
1994:Clostridium innocuum
1945:Intrinsic resistance
1932:Plant tissue culture
1701:Both the vancomycin
1563:Vancomycin exhibits
1546:nonribosomal peptide
902:bacterial infections
7233:does not cross BBB:
6633:2017PNAS..114E5052O
6627:(26): E5052–E5061.
6607:Okano A, Isley NA,
6475:2007EnvMi...9..819L
5982:10.1155/2001/912086
5581:(37): 16039–16050.
5544:10.1038/ja.2017.144
5253:10.1038/nature14141
5245:2015Natur.521..105H
5088:10.1038/nature00907
5080:2002Natur.418..658K
4905:. New York: Wiley.
4581:10.2147/DDDT.S66576
4568:Drug Des Devel Ther
4517:. pp. OA4655.
3911:2019PLoSO..1424561H
2547:Hamilton R (2015).
2430:. 15 October 2020.
2336:. 2 December 2019.
2139:units in Position V
2013:Acquired resistance
1713:Mechanism of action
1685:catalyzed by GtfD.
1558:Nocardia orientalis
1456:Inhaled (off-label)
1232:erythema multiforme
1156:Oral administration
357:(Prescription only)
333:(Prescription only)
25:
7456:Never to phase III
6816:on 17 August 2016.
6753:. Back Bay Books.
6558:(September 2011).
5188:10.1039/C4OB00474D
4901:Dewick PM (2002).
4791:10.1093/jac/dkp085
4743:10.2146/ajhp080434
4108:"Red man syndrome"
2643:(Suppl 1): S5–12.
2579:. September 2015.
2522:10.1093/cid/cir034
2288:. Merriam-Webster.
2230:in Australia. The
1738:
1691:glycorandomization
1664:
1625:
1598:
1472:Rectal (off-label)
1090:empiric antibiotic
973:. It is a type of
963:low blood pressure
955:allergic reactions
412:Excreted unchanged
7806:
7805:
7521:Lipoglycopeptides
7466:
7465:
6906:anti-inflammatory
6782:(suppl): S200-4.
6760:978-0-316-73566-7
6686:(23): 8823–8827.
6680:Angewandte Chemie
6576:10.1021/ja207142h
6149:(suppl): S250-8.
6127:978-1-55581-086-3
5784:on 27 August 2021
5484:978-3-527-61997-9
5436:(19): 2700–2704.
5430:Angewandte Chemie
5390:10.1021/ol3023374
5351:10.1021/ol0501626
4912:978-0-471-49641-0
4837:(12): 2089–2094.
3681:10.1002/phar.2388
3405:(Suppl 1): S3-4.
3349:: bcr2012006347.
2788:978-0-444-63749-9
2752:978-92-4-151552-8
2558:978-1-284-05756-0
2366:. 27 March 2019.
2236:Baxter Healthcare
2088:
2084:
2080:
2076:
2072:
2068:
2064:
2060:
1988:Weissella confusa
1916:
1912:
1908:
1873:
1869:
1864:
1863:
1856:
1807:
1803:
1778:
1774:
1763:
1759:
1755:
1751:
1732:
1728:
1724:
1615:
1058:C. difficile
1006:bacteria of both
891:
890:
825:Interactive image
702:CompTox Dashboard
433:
428:
402:Negligible (oral)
380:
365:
352:
340:
328:
224:
191:
174:
157:
7873:
7823:
7822:
7821:
7814:
7493:
7486:
7479:
7470:
7367:Escherichia coli
7327:Aminosalicylates
7317:Cromoglicic acid
6892:
6885:
6878:
6869:
6862:
6861:
6824:
6818:
6817:
6812:. Archived from
6806:
6800:
6799:
6771:
6765:
6764:
6746:
6740:
6732:
6731:
6727:
6720:
6714:
6713:
6703:
6671:
6665:
6664:
6654:
6644:
6604:
6598:
6597:
6587:
6551:
6545:
6544:
6516:
6510:
6509:
6507:
6505:
6499:
6460:
6451:
6445:
6444:
6405:
6399:
6398:
6361:
6355:
6354:
6344:
6320:
6314:
6313:
6295:
6271:
6265:
6264:
6254:
6230:
6224:
6223:
6217:
6215:
6181:
6173:
6167:
6166:
6138:
6132:
6131:
6109:
6101:
6095:
6094:
6084:
6060:
6054:
6053:
6043:
6011:
6005:
6004:
5994:
5984:
5960:
5954:
5953:
5935:
5911:
5905:
5904:
5894:
5862:
5853:
5852:
5835:(8): 1231–1240.
5824:
5818:
5817:
5815:
5809:. Archived from
5808:
5800:
5794:
5793:
5791:
5789:
5780:. Archived from
5774:
5768:
5767:
5757:
5734:J Clin Microbiol
5725:
5719:
5718:
5708:
5676:
5670:
5669:
5659:
5627:
5621:
5620:
5618:
5616:
5598:
5575:J. Am. Chem. Soc
5572:
5563:
5557:
5556:
5546:
5522:
5516:
5515:
5506:(1–2): 240–244.
5495:
5489:
5488:
5462:
5456:
5455:
5445:
5421:
5412:
5411:
5401:
5369:
5363:
5362:
5334:
5328:
5327:
5291:
5285:
5284:
5282:
5280:
5230:
5222:
5216:
5215:
5213:
5211:
5205:
5190:
5172:
5163:
5157:
5156:
5146:
5129:(18): 6093–100.
5114:
5108:
5107:
5074:(6898): 658–61.
5063:
5057:
5056:
5046:
5037:(26): 15428–35.
5022:
5016:
5015:
5013:
5011:
4993:
4984:(34): 23135–41.
4969:
4963:
4962:
4952:
4928:
4917:
4916:
4898:
4892:
4891:
4880:10.1039/b717538h
4863:
4857:
4856:
4846:
4822:
4816:
4815:
4813:
4811:
4793:
4769:
4763:
4762:
4736:
4715:
4709:
4708:
4688:
4682:
4681:
4645:
4639:
4638:
4610:
4604:
4603:
4593:
4583:
4559:
4553:
4552:
4550:
4548:
4533:
4527:
4526:
4510:
4504:
4503:
4501:
4499:
4493:
4486:
4478:
4472:
4471:
4443:
4437:
4436:
4426:
4394:
4388:
4387:
4377:
4345:
4339:
4338:
4328:
4304:
4298:
4297:
4277:
4271:
4270:
4234:
4225:
4212:
4207:
4206:
4204:
4179:
4173:
4172:
4154:
4148:
4147:
4137:
4127:
4103:
4097:
4096:
4086:
4054:
4048:
4047:
4037:
4027:
4003:
3994:
3993:
3983:
3973:
3949:
3943:
3942:
3932:
3922:
3905:(11): e0224561.
3890:
3884:
3883:
3856:Ann Pharmacother
3850:
3844:
3843:
3833:
3801:
3795:
3794:
3784:
3767:(7): e00079–19.
3752:
3746:
3745:
3709:
3703:
3702:
3692:
3660:
3651:
3650:
3632:
3608:
3602:
3601:
3591:
3559:
3550:
3549:
3539:
3515:
3509:
3508:
3480:
3474:
3473:
3463:
3431:
3425:
3424:
3414:
3390:
3377:
3376:
3366:
3334:
3328:
3327:
3325:
3323:
3304:
3298:
3297:
3287:
3263:
3254:
3253:
3225:
3216:
3215:
3205:
3173:
3160:
3159:
3157:
3155:
3127:
3110:
3109:
3107:
3105:
3090:
3084:
3083:
3081:
3079:
3059:
3053:
3052:
3042:
3010:
3004:
3003:
2976:
2963:
2962:
2942:
2931:
2930:
2910:
2904:
2903:
2893:
2882:10.1002/pro.3819
2861:
2855:
2854:
2836:
2808:
2793:
2792:
2766:
2757:
2756:
2744:
2725:
2719:
2718:
2716:
2697:
2691:
2690:
2688:
2669:
2663:
2662:
2652:
2628:
2611:
2610:
2608:
2606:
2591:
2585:
2584:
2569:
2563:
2562:
2544:
2535:
2534:
2524:
2496:
2490:
2489:
2487:
2485:
2470:
2447:
2446:
2444:
2442:
2436:
2423:
2415:
2409:
2408:
2406:
2404:
2394:nctr-crs.fda.gov
2386:
2380:
2379:
2377:
2375:
2356:
2350:
2349:
2347:
2345:
2326:
2320:
2319:
2317:
2315:
2306:. Archived from
2296:
2290:
2289:
2276:
2228:Aspen Pharmacare
2086:
2082:
2078:
2074:
2070:
2066:
2062:
2058:
1914:
1910:
1906:
1891:
1871:
1867:
1859:
1852:
1848:
1845:
1839:
1819:
1818:
1811:
1805:
1801:
1776:
1772:
1761:
1757:
1753:
1749:
1730:
1726:
1722:
1613:
1548:produced by the
1271:thrombocytopenia
1240:thrombocytopenia
1193:red man syndrome
957:. Occasionally,
887:
886:
827:
807:
805:
788:
782:
776:
770:
764:
747:
736:
725:
724:
710:
708:
693:
673:
653:
645:
625:
605:
585:
565:
555:
554:
542:
532:
531:
517:
431:
426:
421:
378:
375:
370:
363:
360:
350:
347:
339:
336:
326:
323:
301:
291:
281:
222:
219:
201:
190:
187:
184:
173:
170:
167:
156:
153:
140:
126:
108:Vancocin, others
97:
96:
93:
92:
89:
86:
83:
80:
77:
74:
71:
68:
65:
62:
42:
33:
26:
24:
7881:
7880:
7876:
7875:
7874:
7872:
7871:
7870:
7861:Total synthesis
7831:
7830:
7829:
7819:
7817:
7809:
7807:
7802:
7721:
7677:
7639:
7610:
7591:
7568:
7519:
7511:
7497:
7467:
7462:
7461:
7446:Clinical trials
7425:
7391:Albumin tannate
7379:
7354:
7263:corticosteroids
7250:
7168:Antipropulsives
7162:
7108:
6933:
6917:
6896:
6866:
6865:
6826:
6825:
6821:
6808:
6807:
6803:
6773:
6772:
6768:
6761:
6748:
6747:
6743:
6738:Wayback Machine
6729:
6722:
6721:
6717:
6673:
6672:
6668:
6616:
6606:
6605:
6601:
6570:(35): 13946–9.
6553:
6552:
6548:
6518:
6517:
6513:
6503:
6501:
6497:
6458:
6453:
6452:
6448:
6407:
6406:
6402:
6373:(1–2): 95–112.
6363:
6362:
6358:
6322:
6321:
6317:
6286:(23): 2433–41.
6273:
6272:
6268:
6232:
6231:
6227:
6213:
6211:
6175:
6174:
6170:
6140:
6139:
6135:
6128:
6103:
6102:
6098:
6062:
6061:
6057:
6026:(11): 3415–22.
6013:
6012:
6008:
5962:
5961:
5957:
5913:
5912:
5908:
5864:
5863:
5856:
5826:
5825:
5821:
5813:
5806:
5802:
5801:
5797:
5787:
5785:
5776:
5775:
5771:
5727:
5726:
5722:
5678:
5677:
5673:
5629:
5628:
5624:
5614:
5612:
5570:
5565:
5564:
5560:
5524:
5523:
5519:
5497:
5496:
5492:
5485:
5464:
5463:
5459:
5423:
5422:
5415:
5378:Organic Letters
5371:
5370:
5366:
5339:Organic Letters
5336:
5335:
5331:
5293:
5292:
5288:
5278:
5276:
5239:(7550): 105–9.
5224:
5223:
5219:
5209:
5207:
5203:
5170:
5165:
5164:
5160:
5116:
5115:
5111:
5065:
5064:
5060:
5024:
5023:
5019:
5009:
5007:
4971:
4970:
4966:
4930:
4929:
4920:
4913:
4900:
4899:
4895:
4865:
4864:
4860:
4824:
4823:
4819:
4809:
4807:
4771:
4770:
4766:
4717:
4716:
4712:
4690:
4689:
4685:
4650:Pharmacotherapy
4647:
4646:
4642:
4612:
4611:
4607:
4561:
4560:
4556:
4546:
4544:
4535:
4534:
4530:
4512:
4511:
4507:
4497:
4495:
4491:
4484:
4480:
4479:
4475:
4445:
4444:
4440:
4396:
4395:
4391:
4347:
4346:
4342:
4306:
4305:
4301:
4279:
4278:
4274:
4236:
4235:
4228:
4222:Wayback Machine
4202:
4200:
4181:
4180:
4176:
4169:
4156:
4155:
4151:
4105:
4104:
4100:
4056:
4055:
4051:
4005:
4004:
3997:
3951:
3950:
3946:
3892:
3891:
3887:
3852:
3851:
3847:
3803:
3802:
3798:
3754:
3753:
3749:
3711:
3710:
3706:
3669:Pharmacotherapy
3662:
3661:
3654:
3617:Clin Infect Dis
3610:
3609:
3605:
3561:
3560:
3553:
3517:
3516:
3512:
3482:
3481:
3477:
3433:
3432:
3428:
3392:
3391:
3380:
3336:
3335:
3331:
3321:
3319:
3312:medlineplus.gov
3306:
3305:
3301:
3265:
3264:
3257:
3227:
3226:
3219:
3175:
3174:
3163:
3153:
3151:
3129:
3128:
3113:
3103:
3101:
3092:
3091:
3087:
3077:
3075:
3061:
3060:
3056:
3012:
3011:
3007:
2978:
2977:
2966:
2959:
2944:
2943:
2934:
2912:
2911:
2907:
2863:
2862:
2858:
2813:Can J Microbiol
2810:
2809:
2796:
2789:
2768:
2767:
2760:
2753:
2727:
2726:
2722:
2699:
2698:
2694:
2671:
2670:
2666:
2630:
2629:
2614:
2604:
2602:
2593:
2592:
2588:
2571:
2570:
2566:
2559:
2546:
2545:
2538:
2498:
2497:
2493:
2483:
2481:
2472:
2471:
2450:
2440:
2438:
2434:
2421:
2417:
2416:
2412:
2402:
2400:
2388:
2387:
2383:
2373:
2371:
2358:
2357:
2353:
2343:
2341:
2328:
2327:
2323:
2313:
2311:
2298:
2297:
2293:
2278:
2277:
2273:
2268:
2260:
2157:Edmund Kornfeld
2153:
2142:
2125:
2015:
1947:
1942:
1934:
1929:
1928:
1927:
1897:
1892:
1860:
1849:
1843:
1840:
1832:help improve it
1829:
1820:
1816:
1715:
1707:total synthesis
1699:
1697:Total synthesis
1649:stereochemistry
1581:
1536:
1505:pharmacokinetic
1492:
1474:
1458:
1443:
1427:
1411:
1398:
1390:diphenhydramine
1365:
1359:
1350:
1332:
1299:
1217:aminoglycosides
1174:
1158:
1153:
1113:
1104:endophthalmitis
1000:
918:skin infections
882:
880:
875:
872:
867:
862:
861:
850:
847:
842:
841:
830:
803:
801:
791:
785:
779:
773:
767:
728:
704:
696:
676:
656:
628:
608:
588:
568:
551:
545:
528:
520:
500:
497:
460:
459:
429:
419:
398:Bioavailability
390:Pharmacokinetic
384:
368:
305:
237:
230:
211:
204:
59:
55:
17:
12:
11:
5:
7879:
7877:
7869:
7868:
7863:
7858:
7853:
7848:
7843:
7833:
7832:
7828:
7827:
7804:
7803:
7801:
7800:
7795:
7790:
7785:
7780:
7775:
7770:
7765:
7760:
7755:
7750:
7745:
7740:
7735:
7729:
7727:
7723:
7722:
7720:
7719:
7714:
7712:Nitrofurantoin
7709:
7704:
7699:
7694:
7688:
7686:
7679:
7678:
7676:
7675:
7670:
7665:
7660:
7655:
7649:
7647:
7645:Pleuromutilins
7641:
7640:
7638:
7637:
7632:
7627:
7621:
7619:
7612:
7611:
7609:
7608:
7602:
7600:
7599:antibacterials
7593:
7592:
7590:
7589:
7584:
7578:
7576:
7570:
7569:
7567:
7566:
7561:
7556:
7551:
7546:
7541:
7536:
7531:
7525:
7523:
7513:
7512:
7500:Antibacterials
7498:
7496:
7495:
7488:
7481:
7473:
7464:
7463:
7460:
7459:
7458:
7457:
7454:
7443:
7437:
7431:
7430:
7427:
7426:
7424:
7423:
7418:
7413:
7408:
7403:
7398:
7393:
7387:
7385:
7381:
7380:
7378:
7377:
7370:
7362:
7360:
7356:
7355:
7353:
7352:
7351:
7350:
7345:
7340:
7335:
7322:
7321:
7320:
7319:
7305:
7304:
7303:
7302:
7297:
7292:
7287:
7282:
7277:
7275:Hydrocortisone
7272:
7265:acting locally
7258:
7256:
7252:
7251:
7249:
7248:
7238:
7229:
7228:
7223:
7205:
7204:
7198:
7193:
7188:
7181:Opium tincture
7177:
7175:
7164:
7163:
7161:
7160:
7155:
7150:
7145:
7140:
7135:
7125:
7119:
7117:
7110:
7109:
7107:
7106:
7105:
7104:
7102:Broxyquinoline
7091:
7090:
7089:
7088:
7075:
7074:
7073:
7072:
7059:
7058:
7057:
7056:
7051:
7038:
7037:
7036:
7035:
7033:Sulfaguanidine
7030:
7025:
7012:
7011:
7010:
7009:
7004:
6999:
6994:
6989:
6984:
6979:
6974:
6969:
6964:
6959:
6954:
6952:Amphotericin B
6941:
6939:
6935:
6934:
6932:
6931:
6925:
6923:
6919:
6918:
6910:anti-infective
6899:Antidiarrheals
6897:
6895:
6894:
6887:
6880:
6872:
6864:
6863:
6836:(1): 165–176.
6819:
6801:
6766:
6759:
6741:
6715:
6666:
6614:
6599:
6546:
6511:
6446:
6400:
6356:
6315:
6266:
6245:(7): 493–501.
6225:
6190:(10): 710–21.
6168:
6133:
6126:
6096:
6055:
6006:
5955:
5906:
5854:
5819:
5816:on 4 May 2012.
5795:
5769:
5720:
5691:(2): 113–118.
5671:
5622:
5558:
5537:(2): 149–150.
5517:
5490:
5483:
5457:
5413:
5384:(19): 5086–9.
5364:
5329:
5308:10.1038/nbt909
5302:(12): 1467–9.
5286:
5217:
5181:(30): 5574–7.
5158:
5109:
5058:
5017:
4964:
4918:
4911:
4893:
4858:
4817:
4764:
4734:10.1.1.173.737
4710:
4683:
4640:
4605:
4554:
4528:
4505:
4473:
4438:
4389:
4360:(6): 1647–50.
4340:
4326:10.1086/513755
4299:
4272:
4226:
4174:
4167:
4149:
4125:10.1186/cc1871
4098:
4049:
4025:10.1186/cc1516
3995:
3944:
3885:
3845:
3816:(3): 375–383.
3796:
3747:
3720:(7): 1031–48.
3714:Toxicol Pathol
3704:
3675:(5): 438–454.
3652:
3630:10.1086/600877
3603:
3551:
3510:
3475:
3426:
3412:10.1086/491708
3378:
3329:
3299:
3285:10.1086/600884
3255:
3217:
3161:
3111:
3085:
3054:
3005:
2964:
2957:
2932:
2921:(4): 694–700.
2905:
2876:(3): 654–669.
2856:
2794:
2787:
2758:
2751:
2720:
2692:
2664:
2650:10.1086/491709
2612:
2586:
2564:
2557:
2536:
2491:
2448:
2410:
2381:
2351:
2321:
2291:
2270:
2269:
2267:
2264:
2259:
2256:
2220:
2219:
2212:
2197:
2152:
2149:
2140:
2124:
2121:
2116:
2115:
2112:
2109:
2014:
2011:
1976:L. delbrueckii
1970:L. acidophilus
1946:
1943:
1941:
1938:
1933:
1930:
1926:
1925:
1922:
1918:
1903:
1894:
1893:
1886:
1885:
1884:
1862:
1861:
1823:
1821:
1814:
1735:hydrogen bonds
1714:
1711:
1698:
1695:
1580:
1577:
1565:atropisomerism
1550:Actinomycetota
1535:
1532:
1491:
1488:
1473:
1470:
1457:
1454:
1442:
1439:
1426:
1423:
1410:
1407:
1397:
1394:
1386:antihistamines
1358:
1355:
1349:
1346:
1331:
1328:
1298:
1297:Nephrotoxicity
1295:
1264:DRESS syndrome
1236:superinfection
1213:nephrotoxicity
1205:nephrotoxicity
1201:
1200:
1196:
1189:
1173:
1170:
1169:
1168:
1165:
1157:
1154:
1152:
1149:
1148:
1147:
1144:S. epidermidis
1141:
1135:
1112:
1109:
1108:
1107:
1100:
1093:
1086:
1079:
1076:hypersensitive
1068:
1065:
1050:
1047:
1043:S. epidermidis
1037:S. aureus
999:
996:
889:
888:
877:
876:
874:
873:
870:
868:
865:
857:
856:
855:
852:
851:
849:
848:
845:
837:
836:
835:
832:
831:
829:
828:
820:
818:
810:
809:
799:
793:
792:
789:
783:
777:
771:
765:
760:
754:
753:
749:
748:
738:
730:
729:
727:
726:
713:
711:
698:
697:
695:
694:
686:
684:
678:
677:
675:
674:
666:
664:
658:
657:
655:
654:
646:
638:
636:
630:
629:
627:
626:
618:
616:
610:
609:
607:
606:
598:
596:
590:
589:
587:
586:
578:
576:
570:
569:
567:
566:
558:
556:
547:
546:
544:
543:
535:
533:
522:
521:
519:
518:
510:
508:
502:
501:
499:
498:
463:
455:
454:
453:
450:
449:
445:
444:
441:
435:
434:
423:
414:
413:
410:
404:
403:
400:
394:
393:
386:
385:
383:
382:
373:
358:
345:
334:
320:
318:
312:
311:
307:
306:
304:
303:
270:
268:
262:
261:
256:
250:
249:
240:
238:administration
232:
231:
229:
228:
226:
216:
214:
206:
205:
203:
202:
185:
168:
150:
148:
142:
141:
134:
128:
127:
120:
110:
109:
106:
100:
99:
53:
49:
48:
44:
43:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
7878:
7867:
7864:
7862:
7859:
7857:
7854:
7852:
7849:
7847:
7844:
7842:
7839:
7838:
7836:
7826:
7816:
7812:
7799:
7796:
7794:
7791:
7789:
7788:Spectinomycin
7786:
7784:
7781:
7779:
7776:
7774:
7771:
7769:
7768:Mandelic acid
7766:
7764:
7761:
7759:
7756:
7754:
7751:
7749:
7746:
7744:
7741:
7739:
7736:
7734:
7731:
7730:
7728:
7724:
7718:
7717:Nitrofurazone
7715:
7713:
7710:
7708:
7705:
7703:
7700:
7698:
7695:
7693:
7690:
7689:
7687:
7684:
7680:
7674:
7671:
7669:
7666:
7664:
7661:
7659:
7656:
7654:
7651:
7650:
7648:
7646:
7642:
7636:
7633:
7631:
7628:
7626:
7625:Metronidazole
7623:
7622:
7620:
7617:
7613:
7607:
7604:
7603:
7601:
7598:
7594:
7588:
7585:
7583:
7580:
7579:
7577:
7575:
7571:
7565:
7562:
7560:
7557:
7555:
7552:
7550:
7547:
7545:
7542:
7540:
7537:
7535:
7532:
7530:
7527:
7526:
7524:
7522:
7518:
7517:Glycopeptides
7514:
7509:
7505:
7501:
7494:
7489:
7487:
7482:
7480:
7475:
7474:
7471:
7455:
7453:
7450:
7449:
7447:
7444:
7441:
7438:
7436:
7433:
7432:
7428:
7422:
7419:
7417:
7414:
7412:
7409:
7407:
7404:
7402:
7399:
7397:
7394:
7392:
7389:
7388:
7386:
7382:
7376:
7375:
7371:
7369:
7368:
7364:
7363:
7361:
7357:
7349:
7346:
7344:
7341:
7339:
7336:
7334:
7333:Sulfasalazine
7331:
7330:
7329:
7328:
7324:
7323:
7318:
7315:
7314:
7313:
7311:
7307:
7306:
7301:
7300:Beclometasone
7298:
7296:
7293:
7291:
7288:
7286:
7285:Betamethasone
7283:
7281:
7278:
7276:
7273:
7271:
7268:
7267:
7266:
7264:
7260:
7259:
7257:
7253:
7246:
7242:
7239:
7237:
7234:
7231:
7230:
7227:
7224:
7221:
7217:
7216:Diphenoxylate
7214:
7212:
7207:
7206:
7202:
7199:
7197:
7194:
7192:
7189:
7186:
7182:
7179:
7178:
7176:
7173:
7169:
7165:
7159:
7156:
7154:
7151:
7149:
7146:
7144:
7141:
7139:
7136:
7133:
7129:
7126:
7124:
7121:
7120:
7118:
7116:
7111:
7103:
7100:
7099:
7098:
7097:
7093:
7092:
7087:
7084:
7083:
7082:
7081:
7077:
7076:
7071:
7068:
7067:
7066:
7065:
7061:
7060:
7055:
7052:
7050:
7047:
7046:
7045:
7044:
7040:
7039:
7034:
7031:
7029:
7026:
7024:
7021:
7020:
7019:
7018:
7014:
7013:
7008:
7005:
7003:
7000:
6998:
6995:
6993:
6990:
6988:
6985:
6983:
6980:
6978:
6975:
6973:
6970:
6968:
6965:
6963:
6960:
6958:
6955:
6953:
6950:
6949:
6948:
6947:
6943:
6942:
6940:
6936:
6930:
6927:
6926:
6924:
6920:
6915:
6911:
6907:
6904:
6900:
6893:
6888:
6886:
6881:
6879:
6874:
6873:
6870:
6859:
6855:
6851:
6847:
6843:
6839:
6835:
6831:
6823:
6820:
6815:
6811:
6805:
6802:
6797:
6793:
6789:
6785:
6781:
6777:
6770:
6767:
6762:
6756:
6752:
6745:
6742:
6739:
6735:
6725:
6719:
6716:
6711:
6707:
6702:
6697:
6693:
6689:
6685:
6681:
6677:
6670:
6667:
6662:
6658:
6653:
6648:
6643:
6638:
6634:
6630:
6626:
6622:
6618:
6611:(June 2017).
6610:
6603:
6600:
6595:
6591:
6586:
6581:
6577:
6573:
6569:
6565:
6561:
6557:
6550:
6547:
6542:
6538:
6534:
6530:
6526:
6522:
6515:
6512:
6496:
6492:
6488:
6484:
6480:
6476:
6472:
6469:(3): 819–23.
6468:
6464:
6457:
6450:
6447:
6442:
6438:
6434:
6430:
6426:
6422:
6418:
6414:
6410:
6404:
6401:
6396:
6392:
6388:
6384:
6380:
6376:
6372:
6368:
6360:
6357:
6352:
6348:
6343:
6338:
6335:(9): 477–82.
6334:
6330:
6326:
6319:
6316:
6311:
6307:
6303:
6299:
6294:
6289:
6285:
6281:
6277:
6270:
6267:
6262:
6258:
6253:
6248:
6244:
6240:
6236:
6229:
6226:
6222:
6209:
6205:
6201:
6197:
6193:
6189:
6185:
6180:
6172:
6169:
6164:
6160:
6156:
6152:
6148:
6144:
6137:
6134:
6129:
6123:
6119:
6115:
6114:
6108:
6100:
6097:
6092:
6088:
6083:
6078:
6074:
6070:
6066:
6059:
6056:
6051:
6047:
6042:
6037:
6033:
6029:
6025:
6021:
6017:
6010:
6007:
6002:
5998:
5993:
5988:
5983:
5978:
5974:
5970:
5966:
5959:
5956:
5951:
5947:
5943:
5939:
5934:
5929:
5925:
5921:
5917:
5910:
5907:
5902:
5898:
5893:
5888:
5884:
5880:
5876:
5872:
5868:
5861:
5859:
5855:
5850:
5846:
5842:
5838:
5834:
5830:
5823:
5820:
5812:
5805:
5799:
5796:
5783:
5779:
5773:
5770:
5765:
5761:
5756:
5751:
5747:
5743:
5739:
5735:
5731:
5724:
5721:
5716:
5712:
5707:
5702:
5698:
5694:
5690:
5686:
5682:
5675:
5672:
5667:
5663:
5658:
5653:
5649:
5645:
5642:(7): 1342–7.
5641:
5637:
5633:
5626:
5623:
5610:
5606:
5602:
5597:
5592:
5588:
5584:
5580:
5576:
5569:
5562:
5559:
5554:
5550:
5545:
5540:
5536:
5532:
5529:. Editorial.
5528:
5521:
5518:
5513:
5509:
5505:
5501:
5494:
5491:
5486:
5480:
5476:
5472:
5468:
5461:
5458:
5453:
5449:
5444:
5439:
5435:
5431:
5427:
5420:
5418:
5414:
5409:
5405:
5400:
5395:
5391:
5387:
5383:
5379:
5375:
5368:
5365:
5360:
5356:
5352:
5348:
5345:(8): 1513–5.
5344:
5340:
5333:
5330:
5325:
5321:
5317:
5313:
5309:
5305:
5301:
5297:
5290:
5287:
5274:
5270:
5266:
5262:
5258:
5254:
5250:
5246:
5242:
5238:
5234:
5229:
5221:
5218:
5202:
5198:
5194:
5189:
5184:
5180:
5176:
5169:
5162:
5159:
5154:
5150:
5145:
5140:
5136:
5132:
5128:
5124:
5120:
5113:
5110:
5105:
5101:
5097:
5093:
5089:
5085:
5081:
5077:
5073:
5069:
5062:
5059:
5054:
5050:
5045:
5040:
5036:
5032:
5028:
5021:
5018:
5005:
5001:
4997:
4992:
4987:
4983:
4979:
4975:
4968:
4965:
4960:
4956:
4951:
4946:
4943:(3): 155–62.
4942:
4938:
4934:
4927:
4925:
4923:
4919:
4914:
4908:
4904:
4897:
4894:
4889:
4885:
4881:
4877:
4874:(5): 387–93.
4873:
4869:
4862:
4859:
4854:
4850:
4845:
4840:
4836:
4832:
4828:
4821:
4818:
4805:
4801:
4797:
4792:
4787:
4784:(5): 1050–7.
4783:
4779:
4775:
4768:
4765:
4760:
4756:
4752:
4748:
4744:
4740:
4735:
4730:
4726:
4722:
4714:
4711:
4706:
4702:
4699:(10): 631–4.
4698:
4694:
4687:
4684:
4679:
4675:
4671:
4667:
4663:
4659:
4656:(3): 257–66.
4655:
4651:
4644:
4641:
4636:
4632:
4628:
4624:
4620:
4616:
4609:
4606:
4601:
4597:
4592:
4587:
4582:
4577:
4573:
4569:
4565:
4558:
4555:
4542:
4538:
4532:
4529:
4524:
4520:
4516:
4509:
4506:
4490:
4483:
4477:
4474:
4469:
4465:
4461:
4457:
4454:(3): 221–33.
4453:
4449:
4442:
4439:
4434:
4430:
4425:
4420:
4416:
4412:
4408:
4404:
4400:
4393:
4390:
4385:
4381:
4376:
4371:
4367:
4363:
4359:
4355:
4351:
4344:
4341:
4336:
4332:
4327:
4322:
4319:(3): 729–32.
4318:
4314:
4310:
4303:
4300:
4295:
4291:
4287:
4283:
4276:
4273:
4268:
4264:
4260:
4256:
4252:
4248:
4244:
4240:
4233:
4231:
4227:
4223:
4219:
4216:
4211:
4198:
4194:
4190:
4186:
4185:
4178:
4175:
4170:
4168:0-7216-2921-0
4164:
4160:
4153:
4150:
4145:
4141:
4136:
4131:
4126:
4121:
4118:(2): 119–20.
4117:
4113:
4112:Critical Care
4109:
4102:
4099:
4094:
4090:
4085:
4080:
4076:
4072:
4068:
4064:
4060:
4053:
4050:
4045:
4041:
4036:
4031:
4026:
4021:
4017:
4013:
4009:
4002:
4000:
3996:
3991:
3987:
3982:
3977:
3972:
3967:
3963:
3959:
3955:
3948:
3945:
3940:
3936:
3931:
3926:
3921:
3916:
3912:
3908:
3904:
3900:
3896:
3889:
3886:
3881:
3877:
3873:
3869:
3865:
3861:
3857:
3849:
3846:
3841:
3837:
3832:
3827:
3823:
3819:
3815:
3811:
3810:Crit Care Med
3807:
3800:
3797:
3792:
3788:
3783:
3778:
3774:
3770:
3766:
3762:
3758:
3751:
3748:
3743:
3739:
3735:
3731:
3727:
3723:
3719:
3715:
3708:
3705:
3700:
3696:
3691:
3686:
3682:
3678:
3674:
3670:
3666:
3659:
3657:
3653:
3648:
3644:
3640:
3636:
3631:
3626:
3622:
3618:
3614:
3607:
3604:
3599:
3595:
3590:
3585:
3581:
3577:
3574:(1): 138–41.
3573:
3569:
3565:
3558:
3556:
3552:
3547:
3543:
3538:
3533:
3530:(9): 904–10.
3529:
3525:
3521:
3514:
3511:
3506:
3502:
3498:
3494:
3491:(2): 165–71.
3490:
3486:
3479:
3476:
3471:
3467:
3462:
3457:
3453:
3449:
3446:(1): 138–41.
3445:
3441:
3437:
3430:
3427:
3422:
3418:
3413:
3408:
3404:
3400:
3396:
3389:
3387:
3385:
3383:
3379:
3374:
3370:
3365:
3360:
3356:
3352:
3348:
3344:
3340:
3333:
3330:
3317:
3313:
3309:
3303:
3300:
3295:
3291:
3286:
3281:
3278:(4): 507–14.
3277:
3273:
3269:
3262:
3260:
3256:
3251:
3247:
3243:
3239:
3236:(4): 533–43.
3235:
3231:
3224:
3222:
3218:
3213:
3209:
3204:
3199:
3195:
3191:
3187:
3183:
3179:
3172:
3170:
3168:
3166:
3162:
3149:
3145:
3141:
3137:
3133:
3126:
3124:
3122:
3120:
3118:
3116:
3112:
3099:
3095:
3089:
3086:
3073:
3069:
3065:
3058:
3055:
3050:
3046:
3041:
3036:
3032:
3028:
3024:
3020:
3016:
3009:
3006:
3001:
2997:
2993:
2989:
2985:
2981:
2975:
2973:
2971:
2969:
2965:
2960:
2958:0-9757919-2-3
2954:
2950:
2949:
2941:
2939:
2937:
2933:
2928:
2924:
2920:
2916:
2909:
2906:
2901:
2897:
2892:
2887:
2883:
2879:
2875:
2871:
2867:
2860:
2857:
2852:
2848:
2844:
2840:
2835:
2830:
2826:
2822:
2818:
2814:
2807:
2805:
2803:
2801:
2799:
2795:
2790:
2784:
2780:
2776:
2772:
2765:
2763:
2759:
2754:
2748:
2743:
2738:
2734:
2730:
2724:
2721:
2715:
2710:
2706:
2702:
2696:
2693:
2687:
2682:
2678:
2674:
2668:
2665:
2660:
2656:
2651:
2646:
2642:
2638:
2634:
2627:
2625:
2623:
2621:
2619:
2617:
2613:
2600:
2596:
2590:
2587:
2582:
2578:
2574:
2568:
2565:
2560:
2554:
2550:
2543:
2541:
2537:
2532:
2528:
2523:
2518:
2515:(3): 285–92.
2514:
2510:
2506:
2504:
2495:
2492:
2479:
2475:
2469:
2467:
2465:
2463:
2461:
2459:
2457:
2455:
2453:
2449:
2433:
2429:
2428:
2420:
2414:
2411:
2399:
2395:
2391:
2385:
2382:
2369:
2365:
2361:
2355:
2352:
2339:
2335:
2331:
2325:
2322:
2309:
2305:
2301:
2295:
2292:
2287:
2286:
2281:
2275:
2272:
2265:
2263:
2257:
2255:
2253:
2249:
2245:
2241:
2237:
2233:
2229:
2225:
2217:
2213:
2210:
2206:
2202:
2198:
2195:
2194:
2193:
2191:
2186:
2184:
2178:
2176:
2172:
2171:
2166:
2162:
2158:
2150:
2148:
2146:
2138:
2134:
2130:
2122:
2120:
2113:
2110:
2107:
2103:
2102:
2101:
2100:populations:
2099:
2095:
2090:
2055:
2053:
2049:
2048:
2042:
2041:
2035:
2034:
2028:
2024:
2020:
2017:Evolution of
2012:
2010:
2008:
2007:
2003:
1998:
1996:
1995:
1990:
1989:
1984:
1983:
1978:
1977:
1972:
1971:
1966:
1965:
1964:Lactobacillus
1960:
1959:
1954:
1953:
1944:
1939:
1937:
1931:
1923:
1919:
1904:
1901:
1900:
1896:
1890:
1883:
1881:
1877:
1858:
1855:
1847:
1837:
1833:
1827:
1824:This article
1822:
1813:
1812:
1809:
1799:
1798:hydrogen bond
1795:
1790:
1788:
1787:
1780:
1769:
1765:
1747:
1743:
1736:
1719:
1712:
1710:
1708:
1704:
1696:
1694:
1692:
1686:
1684:
1680:
1676:
1675:glycosylation
1671:
1668:
1660:
1656:
1654:
1650:
1646:
1645:epimerization
1642:
1638:
1634:
1630:
1621:
1617:
1611:
1607:
1603:
1594:
1590:
1588:
1587:
1578:
1576:
1574:
1570:
1566:
1561:
1559:
1555:
1551:
1547:
1544:
1541:
1533:
1531:
1529:
1524:
1523:trough levels
1520:
1519:trough levels
1515:
1512:
1510:
1509:haemodialysis
1506:
1502:
1498:
1489:
1487:
1485:
1484:
1479:
1471:
1469:
1467:
1463:
1455:
1453:
1451:
1450:
1440:
1438:
1436:
1432:
1431:intravenously
1424:
1422:
1420:
1416:
1415:United States
1408:
1406:
1402:
1395:
1393:
1391:
1387:
1383:
1379:
1375:
1371:
1364:
1356:
1354:
1347:
1345:
1342:
1337:
1329:
1327:
1325:
1320:
1318:
1314:
1311:
1307:
1303:
1296:
1294:
1292:
1286:
1284:
1280:
1276:
1272:
1267:
1265:
1261:
1257:
1253:
1249:
1245:
1241:
1237:
1233:
1229:
1225:
1220:
1218:
1214:
1210:
1206:
1197:
1194:
1190:
1187:
1186:
1185:
1183:
1178:
1171:
1166:
1163:
1162:
1161:
1155:
1150:
1145:
1142:
1139:
1136:
1133:
1130:
1129:
1128:
1126:
1122:
1118:
1110:
1105:
1102:treatment of
1101:
1098:
1094:
1091:
1087:
1084:
1080:
1077:
1073:
1069:
1066:
1063:
1062:metronidazole
1059:
1055:
1052:treatment of
1051:
1048:
1045:
1044:
1039:
1038:
1032:
1028:
1027:
1026:
1024:
1020:
1015:
1013:
1009:
1005:
1004:Gram-positive
997:
995:
993:
992:
987:
982:
980:
976:
972:
971:breastfeeding
968:
964:
960:
956:
951:
949:
947:
942:
938:
937:
931:
927:
923:
919:
915:
911:
907:
906:intravenously
904:. It is used
903:
899:
895:
885:
878:
869:
864:
860:
853:
844:
840:
833:
826:
822:
821:
819:
816:
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800:
798:
794:
761:
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750:
746:
742:
739:
737:
735:ECHA InfoCard
731:
723:
719:
718:DTXSID0042664
715:
714:
712:
703:
699:
692:
688:
687:
685:
683:
679:
672:
668:
667:
665:
663:
659:
652:
648:as HCl:
647:
644:
640:
639:
637:
635:
631:
624:
620:
619:
617:
615:
611:
604:
600:
599:
597:
595:
591:
584:
580:
579:
577:
575:
571:
564:
560:
559:
557:
550:PubChem
548:
541:
537:
536:
534:
527:
523:
516:
512:
511:
509:
507:
503:
495:
491:
487:
483:
479:
475:
471:
467:
462:
458:
451:
446:
442:
440:
436:
424:
422:
415:
411:
409:
405:
401:
399:
395:
391:
387:
381: Rx-only
374:
371:
359:
356:
346:
344:
335:
332:
322:
321:
319:
317:
313:
308:
300:
295:
290:
285:
280:
275:
272:
271:
269:
267:
263:
260:
257:
255:
251:
248:
244:
241:
239:
233:
227:
218:
217:
215:
213:
207:
200:
196:
186:
183:
178:
169:
166:
161:
152:
151:
149:
147:
143:
139:
135:
133:
129:
125:
121:
119:
115:
111:
107:
105:
101:
95:
54:
52:Pronunciation
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
7856:Nephrotoxins
7697:Nifuroxazide
7692:Furazolidone
7606:Fusidic acid
7563:
7416:Racecadotril
7372:
7365:
7325:
7310:antiallergic
7308:
7270:Prednisolone
7261:
7245:+simethicone
7232:
7208:
7148:Crospovidone
7096:Oxyquinoline
7094:
7078:
7062:
7049:Nifuroxazide
7041:
7017:Sulfonamides
7015:
7006:
7002:Streptomycin
6944:
6833:
6830:J Orthop Sci
6829:
6822:
6814:the original
6804:
6779:
6775:
6769:
6750:
6744:
6724:EP 3846854A2
6718:
6683:
6679:
6669:
6624:
6620:
6602:
6567:
6563:
6549:
6524:
6520:
6514:
6502:. Retrieved
6466:
6462:
6449:
6419:(3): 144–6.
6416:
6412:
6409:Collignon PJ
6403:
6370:
6366:
6359:
6332:
6328:
6318:
6283:
6279:
6269:
6242:
6238:
6228:
6219:
6214:11 September
6212:. Retrieved
6187:
6183:
6171:
6146:
6142:
6136:
6112:
6099:
6072:
6068:
6058:
6023:
6019:
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5975:(4): 254–6.
5972:
5968:
5958:
5926:(2): 153–4.
5923:
5919:
5909:
5877:(4): 543–9.
5874:
5870:
5832:
5828:
5822:
5811:the original
5798:
5788:10 September
5786:. Retrieved
5782:the original
5772:
5737:
5733:
5723:
5688:
5684:
5674:
5639:
5635:
5625:
5613:. Retrieved
5578:
5574:
5561:
5534:
5530:
5520:
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5499:
5493:
5466:
5460:
5433:
5429:
5381:
5377:
5367:
5342:
5338:
5332:
5299:
5295:
5289:
5277:. Retrieved
5236:
5232:
5220:
5208:. Retrieved
5178:
5174:
5161:
5126:
5122:
5112:
5071:
5067:
5061:
5034:
5030:
5020:
5008:. Retrieved
4981:
4977:
4967:
4940:
4936:
4902:
4896:
4871:
4867:
4861:
4834:
4830:
4820:
4810:15 September
4808:. Retrieved
4781:
4777:
4767:
4727:(1): 82–98.
4724:
4720:
4713:
4696:
4692:
4686:
4653:
4649:
4643:
4621:(4): 544–6.
4618:
4614:
4608:
4571:
4567:
4557:
4545:. Retrieved
4531:
4514:
4508:
4496:. Retrieved
4476:
4451:
4447:
4441:
4406:
4402:
4392:
4357:
4353:
4343:
4316:
4312:
4302:
4288:(8): 740–9.
4285:
4281:
4275:
4242:
4238:
4201:, retrieved
4183:
4177:
4158:
4152:
4115:
4111:
4101:
4066:
4062:
4052:
4018:(4): 313–6.
4015:
4011:
3961:
3958:Front Neurol
3957:
3947:
3902:
3898:
3888:
3855:
3848:
3813:
3809:
3799:
3764:
3760:
3750:
3717:
3713:
3707:
3672:
3668:
3623:(3): 325–7.
3620:
3616:
3606:
3571:
3567:
3527:
3523:
3513:
3488:
3484:
3478:
3443:
3439:
3429:
3402:
3398:
3346:
3343:BMJ Case Rep
3342:
3332:
3320:. Retrieved
3311:
3302:
3275:
3271:
3233:
3229:
3185:
3181:
3152:. Retrieved
3135:
3132:"Vancomycin"
3102:. Retrieved
3088:
3076:. Retrieved
3067:
3057:
3025:(1): 117–8.
3022:
3018:
3008:
2987:
2983:
2946:
2918:
2914:
2908:
2873:
2869:
2859:
2819:(1): 11–16.
2816:
2812:
2770:
2742:10665/312266
2732:
2723:
2714:10665/345533
2704:
2695:
2686:10665/325771
2676:
2667:
2640:
2636:
2603:. Retrieved
2589:
2576:
2567:
2548:
2512:
2508:
2502:
2494:
2482:. Retrieved
2439:. Retrieved
2425:
2413:
2401:. Retrieved
2393:
2384:
2372:. Retrieved
2363:
2354:
2342:. Retrieved
2333:
2330:"Vancomycin"
2324:
2312:. Retrieved
2308:the original
2294:
2283:
2280:"vancomycin"
2274:
2261:
2221:
2189:
2187:
2179:
2174:
2168:
2159:(working at
2154:
2133:oligopeptide
2126:
2117:
2097:
2093:
2091:
2056:
2046:
2039:
2033:Enterococcus
2032:
2016:
2004:
1999:
1992:
1986:
1980:
1974:
1968:
1962:
1956:
1950:
1948:
1935:
1879:
1875:
1865:
1850:
1841:
1825:
1791:
1784:
1781:
1770:
1766:
1739:
1700:
1687:
1678:
1672:
1669:
1665:
1653:thioesterase
1626:
1599:
1584:
1582:
1579:Biosynthesis
1562:
1557:
1553:
1543:glycosylated
1537:
1516:
1513:
1493:
1481:
1475:
1459:
1447:
1444:
1428:
1412:
1403:
1399:
1388:, including
1370:erythematous
1366:
1363:Erythroderma
1351:
1333:
1321:
1315:
1312:
1308:
1304:
1300:
1287:
1268:
1221:
1202:
1179:
1175:
1159:
1151:Side effects
1143:
1137:
1131:
1114:
1072:endocarditis
1057:
1041:
1036:
1016:
1001:
998:Medical uses
989:
983:
959:hearing loss
952:
945:
935:
926:endocarditis
893:
892:
881:
691:ChEMBL262777
493:
489:
485:
481:
477:
473:
469:
465:
430:6 d to 10 d
425:4 h to 11 h
418:Elimination
316:Legal status
310:Legal status
146:License data
18:
7778:Nitroxoline
7773:Methenamine
7753:Furaltadone
7702:Nifurtoinol
7685:derivatives
7663:Retapamulin
7618:derivatives
7587:Polymyxin B
7554:Teicoplanin
7544:Oritavancin
7539:Dalbavancin
7442:from market
7348:Balsalazide
7236:Eluxadoline
7203:(paregoric)
7158:Diosmectite
7153:Attapulgite
7130:(including
7113:Intestinal
6992:Polymyxin B
6987:Paromomycin
6962:Fidaxomicin
6946:Antibiotics
6922:Rehydration
6527:: 381–408.
5740:(1): 94–9.
4574:: 1065–72.
4203:25 February
3136:StatPearls
3104:26 February
3068:www.fda.gov
2870:Protein Sci
2605:5 September
2484:4 September
2374:24 December
2344:24 December
2209:cloxacillin
2201:methicillin
2106:teicoplanin
2098:E. faecalis
2043:(VISA) and
2025:(2000) and
1958:Pediococcus
1952:Leuconostoc
1794:hydrophilic
1683:vancosamine
1610:amino acids
1486:infection.
1425:Intravenous
1378:hypotension
1336:ototoxicity
1330:Ototoxicity
1260:ototoxicity
1244:neutropenia
1224:anaphylaxis
1209:ototoxicity
1199:thrombosis.
1019:enterococci
808: g·mol
741:100.014.338
671:CHEBI:28001
448:Identifiers
243:Intravenous
132:MedlinePlus
104:Trade names
7835:Categories
7783:Novobiocin
7748:Fosfomycin
7743:Daptomycin
7733:Bacitracin
7683:Nitrofuran
7673:Valnemulin
7635:Tinidazole
7630:Ornidazole
7574:Polymyxins
7564:Vancomycin
7559:Telavancin
7549:Ristocetin
7534:Corbomycin
7502:: others (
7421:Kaopectate
7411:Octreotide
7406:Crofelemer
7343:Olsalazine
7338:Mesalazine
7295:Budesonide
7290:Tixocortol
7280:Prednisone
7241:Loperamide
7115:adsorbents
7070:Miconazole
7043:Nitrofuran
7007:Vancomycin
6903:intestinal
5210:2 February
4245:: 110728.
4184:Vancomycin
3964:: 652674.
2834:1807/96894
2474:"Vancocin"
2403:22 October
2314:20 January
2266:References
2224:ViroPharma
2027:daptomycin
2009:species).
2002:gonococcal
1844:March 2024
1792:The large
1756:-alanine (
1655:scission.
1382:angioedema
1361:See also:
1281:, and wet
1279:ecchymoses
1248:leukopenia
1083:prostheses
1056:caused by
932:caused by
930:meningitis
894:Vancomycin
813:3D model (
797:Molar mass
623:6Q205EH1VU
594:ChemSpider
506:CAS Number
457:IUPAC name
408:Metabolism
254:Drug class
199:Vancomycin
182:Vancomycin
23:Vancomycin
7793:Tedizolid
7763:Linezolid
7758:Lefamulin
7738:Clofoctol
7707:Nifurzide
7658:Lefamulin
7616:Imidazole
7529:Avoparcin
7452:Phase III
7440:Withdrawn
7401:Ceratonia
7226:Difenoxin
7220:+atropine
7086:Acetarsol
7080:Arsenical
7064:Imidazole
7054:Nifurzide
6997:Rifaximin
6972:Natamycin
6967:Kanamycin
6858:254215681
5950:221924592
4729:CiteSeerX
4267:267502279
4069:(1): e5.
4012:Crit Care
3880:267300725
3188:: 33–39.
3078:6 October
2851:202745549
2364:Drugs.com
2334:Drugs.com
2216:inner ear
2205:nafcillin
2190:S. aureus
2161:Eli Lilly
2052:avoparcin
2047:S. aureus
2040:S. aureus
2023:linezolid
2006:Neisseria
1786:Neisseria
1746:anaerobic
1573:conformer
1540:tricyclic
1534:Chemistry
1478:off-label
1466:nebulizer
1462:off-label
1256:dizziness
1138:S. aureus
1132:S. aureus
1031:resistant
1012:anaerobic
979:cell wall
910:injection
515:1404-90-6
439:Excretion
420:half-life
236:Routes of
210:Pregnancy
124:Monograph
118:Drugs.com
7825:Medicine
7798:Xibornol
7668:Tiamulin
7653:Azamulin
7582:Colistin
7209:crosses
7196:Morphine
7185:laudanum
7123:Charcoal
6982:Nystatin
6977:Neomycin
6957:Colistin
6912:agents (
6850:36470703
6734:Archived
6710:32190958
6661:28559345
6609:Boger DL
6594:21823662
6556:Boger DL
6541:11807177
6504:20 April
6495:Archived
6491:17298380
6441:24378463
6433:10474607
6351:11168181
6310:43628397
6302:16322603
6261:10021469
6208:Archived
6204:10706902
6091:21596906
6050:15150227
6001:18159347
5849:84495391
5715:30408494
5685:J Infect
5609:Archived
5605:32885969
5553:29375134
5452:29711601
5408:22984807
5359:15816740
5316:14608364
5273:Archived
5261:25686610
5201:Archived
5197:24756572
5153:15342578
5096:12167866
5004:Archived
4888:18414736
4853:31534058
4804:Archived
4800:19299472
4759:11692065
4751:19106348
4678:24947921
4670:10221365
4600:25143711
4541:Archived
4489:Archived
4468:25533880
4433:31964790
4384:12019070
4294:16955686
4259:38325652
4218:Archived
4197:archived
4193:31644188
4144:12720556
4093:28367504
4044:12225605
3990:33767665
3939:31693679
3899:PLOS ONE
3872:38279799
3840:29189343
3791:30988153
3742:45358082
3734:22581810
3699:32239518
3647:32585259
3639:19569969
3546:17329697
3505:22525393
3421:16323117
3373:22669879
3316:Archived
3294:19586413
3212:38304144
3203:10831154
3148:Archived
3144:29083794
3098:Archived
3072:Archived
3049:10691328
3000:Archived
2927:25753888
2900:31899563
2843:31545906
2731:(2019).
2703:(2021).
2675:(2019).
2659:16323120
2599:Archived
2581:Archived
2531:21217178
2478:Archived
2441:27 April
2432:Archived
2368:Archived
2338:Archived
2258:Research
2085:-alanyl-
2077:-alanyl-
2069:-alanyl-
2061:-alanyl-
1804:-alanyl-
1752:-alanyl-
1703:aglycone
1569:rotamers
1552:species
1252:tinnitus
884:(verify)
574:DrugBank
563:46505261
266:ATC code
225: B2
212:category
177:DailyMed
7597:Steroid
7191:Codeine
7172:opioids
7128:Bismuth
6796:7043707
6701:7323874
6652:5495262
6629:Bibcode
6585:3164945
6471:Bibcode
6395:4958557
6387:9234429
6163:7342289
5992:2094827
5942:9569701
5901:2344161
5764:6790572
5706:7224403
5666:2386365
5615:13 July
5596:7501256
5399:3489467
5324:2469387
5279:23 June
5269:4466657
5241:Bibcode
5104:4380296
5076:Bibcode
5053:8663196
5000:1744112
4959:9545426
4635:8038307
4591:4136957
4547:19 July
4498:19 July
4424:7038285
4335:9314469
4084:5375112
3981:7985331
3930:6834250
3907:Bibcode
3831:5821475
3782:6591602
3690:7331087
3598:6219616
3470:6219616
3364:4543351
3322:19 July
3250:8038306
3154:19 July
3040:1723217
2996:7565541
2891:7020976
2252:Hospira
2248:Strides
2151:History
2137:arginin
1921:enzyme.
1830:Please
1742:aerobic
1633:protein
1629:modules
1606:enzymes
1413:In the
1374:MRGPRX2
1283:purpura
1258:and/or
1180:Common
1046:(MRSE),
1008:aerobic
948:colitis
912:into a
758:Formula
583:DB00512
526:PubChem
372:Rx-only
369:WARNING
341::
296: (
294:S01AA28
286: (
284:J01XA01
282:)
276: (
274:A07AA09
197::
179::
162::
138:a604038
7811:Portal
7435:WHO-EM
7143:Kaolin
7138:Pectin
6856:
6848:
6794:
6757:
6730:
6708:
6698:
6659:
6649:
6592:
6582:
6539:
6489:
6439:
6431:
6393:
6385:
6349:
6308:
6300:
6259:
6202:
6161:
6124:
6089:
6048:
6041:415764
6038:
5999:
5989:
5948:
5940:
5899:
5892:171641
5889:
5847:
5762:
5755:271907
5752:
5713:
5703:
5664:
5657:175978
5654:
5603:
5593:
5551:
5481:
5450:
5406:
5396:
5357:
5322:
5314:
5267:
5259:
5233:Nature
5195:
5151:
5144:515157
5141:
5102:
5094:
5068:Nature
5051:
5010:3 June
4998:
4957:
4909:
4886:
4851:
4798:
4757:
4749:
4731:
4705:909314
4703:
4676:
4668:
4633:
4598:
4588:
4466:
4431:
4421:
4382:
4375:127235
4372:
4333:
4292:
4265:
4257:
4191:
4165:
4142:
4135:270616
4132:
4091:
4081:
4042:
4035:137311
4032:
3988:
3978:
3937:
3927:
3878:
3870:
3838:
3828:
3789:
3779:
3740:
3732:
3697:
3687:
3645:
3637:
3596:
3589:184631
3586:
3544:
3503:
3468:
3461:184631
3458:
3419:
3371:
3361:
3292:
3248:
3210:
3200:
3142:
3047:
3037:
2994:
2955:
2925:
2898:
2888:
2849:
2841:
2785:
2749:
2657:
2555:
2529:
2250:, and
2240:Sandoz
2232:patent
2165:Borneo
1991:, and
1464:, via
1435:mucosa
1262:, and
1117:sepsis
941:orally
839:SMILES
682:ChEMBL
651:D00926
643:D00212
366:
353:
343:℞-only
329:
192:
175:
165:by INN
158:
98:
7508:D06AX
6854:S2CID
6498:(PDF)
6459:(PDF)
6437:S2CID
6391:S2CID
6306:S2CID
5946:S2CID
5845:S2CID
5814:(PDF)
5807:(PDF)
5571:(PDF)
5320:S2CID
5265:S2CID
5204:(PDF)
5171:(PDF)
5100:S2CID
4755:S2CID
4674:S2CID
4492:(PDF)
4485:(PDF)
4409:(3).
4263:S2CID
3876:S2CID
3738:S2CID
3643:S2CID
2847:S2CID
2435:(PDF)
2422:(PDF)
2244:Akorn
1870:-Ala-
1775:-Ala-
1760:-Ala-
1729:-Ala-
1725:-Lys-
1637:amide
965:, or
896:is a
859:InChI
815:JSmol
662:ChEBI
603:14253
540:14969
7504:J01X
6908:and
6846:PMID
6792:PMID
6755:ISBN
6706:PMID
6657:PMID
6590:PMID
6537:PMID
6506:2018
6487:PMID
6429:PMID
6383:PMID
6347:PMID
6298:PMID
6257:PMID
6216:2022
6200:PMID
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