1280:, and generalized weakness. The violent chills and fevers have caused the drug to be nicknamed "shake and bake". The precise etiology of the reaction is unclear, although it may involve increased prostaglandin synthesis and the release of cytokines from macrophages. Deoxycholate formulations (ABD) may also stimulate the release of histamine from mast cells and basophils. Reactions sometimes subside with later applications of the drug. This nearly universal febrile response necessitates a critical (and diagnostically difficult) professional determination as to whether the onset of high fever is a novel symptom of a fast-progressing disease, or merely the effect of the drug. To decrease the likelihood and severity of the symptoms, initial doses should be low, and increased slowly.
1509:β-ketoacyl intermediate. The growing chain is constructed by a series of Claisen reactions. Within each module, the extender units are loaded onto the current ACP domain by acetyl transferase (AT). The ACP-bound elongation group reacts in a Claisen condensation with the KS-bound polyketide chain. Ketoreductase (KR), dehydratase (DH) and enoyl reductase (ER) enzymes may also be present to form alcohol, double bonds or single bonds. After cyclisation, the macrolactone core undergoes further modification by hydroxylation, methylation and glycosylation. The order of these three post-cyclization processes is unknown.
51:
733:
667:
644:
42:
785:
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
1493:
host membrane as well as the fungal membrane. This impairment in membrane barrier function can have lethal effects. Ergosterol, the fungal sterol, is more sensitive to amphotericin B than cholesterol, the common mammalian sterol. Reactivity with the membrane is also sterol concentration dependent. Bacteria are not affected as their cell membranes do not usually contain sterols.
6672:
1457:) and subsequent fungal cell death. This is amphotericin B's primary effect as an antifungal agent. It has been found that the amphotericin B/ergosterol bimolecular complex that maintains these pores is stabilized by Van der Waals interactions. Researchers have found evidence that amphotericin B also causes
2736:
Wasan EK, Bartlett K, Gershkovich P, Sivak O, Banno B, Wong Z, et al. (May 2009). "Development and characterization of oral lipid-based amphotericin B formulations with enhanced drug solubility, stability and antifungal activity in rats infected with
Aspergillus fumigatus or Candida albicans".
1492:
Mammalian and fungal membranes both contain sterols, a primary membrane target for amphotericin B. Because mammalian and fungal membranes are similar in structure and composition, this is one mechanism by which amphotericin B causes cellular toxicity. Amphotericin B molecules can form pores in the
1132:
of 7. Therefore, several formulations have been devised to improve its intravenous bioavailability. Lipid-based formulations of amphotericin B are no more effective than conventional formulations, although there is some evidence that lipid-based formulations may be better tolerated by patients and
1303:
is a frequently reported side effect, and can be severe and/or irreversible. Less kidney toxicity has been reported with liposomal formulations (such as AmBisome) and it has become preferred in patients with preexisting renal injury. The integrity of the liposome is disrupted when it binds to the
1238:
and polymeric nanoparticles—such as amphotericin B in pegylated polylactide coglycolide copolymer nanoparticles—have demonstrated potential for oral formulation of amphotericin B. The oral lipid nanocrystal amphotericin by
Matinas Biopharma is furthest along having completed a successful phase 2
1201:
in 1995. It consists of amphotericin B and two lipids in a 1:1 ratio that form large ribbon-like structures. Amphotec is a complex of amphotericin and sodium cholesteryl sulfate in a 1:1 ratio. Two molecules of each form a tetramer that aggregate into spiral arms on a disk-like complex. It was
1508:
components. The carbon chains of amphotericin B are assembled from sixteen 'C2' acetate and three 'C3'propionate units by polyketide syntheses (PKSs). Polyketide biosynthesis begins with the decarboxylative condensation of a dicarboxylic acid extender unit with a starter acyl unit to form a
1157:
In order to improve the tolerability of amphotericin and reduce toxicity, several lipid formulations have been developed. Liposomal formulations have been found to have less renal toxicity than deoxycholate, and fewer infusion-related reactions. They are more expensive than amphotericin B
2268:
Steimbach, Laiza M., Fernanda S. Tonin, Suzane
Virtuoso, Helena HL Borba, Andréia CC Sanches, Astrid Wiens, Fernando Fernandez-Llimós, and Roberto Pontarolo. "Efficacy and safety of amphotericin B lipid-based formulations—A systematic review and meta-analysis." Mycoses 60, no. 3 (2017):
1561:
It is a subgroup of the macrolide antibiotics, and exhibits similar structural elements. Currently, the drug is available in many forms. Either "conventionally" complexed with sodium deoxycholate (ABD), as a cholesteryl sulfate complex (ABCD), as a lipid complex (ABLC), and as a
4381:
4374:
3700:
Vertut-Croquin A, Bolard J, Chabbert M, Gary-Bobo C (June 1983). "Differences in the interaction of the polyene antibiotic amphotericin B with cholesterol- or ergosterol-containing phospholipid vesicles. A circular dichroism and permeability study".
1247:
Amphotericin B is well known for its severe and potentially lethal side effects, earning it the nickname "amphoterrible". Very often, it causes a serious reaction soon after infusion (within 1 to 3 hours), consisting of high fever, shaking chills,
1541:. Two antifungal substances were isolated from the soil culture, amphotericin A and amphotericin B, but B had better antifungal activity. For decades it remained the only effective therapy for invasive fungal disease until the development of the
4367:
1358:: Toxicity of flucytosine is increased and allows a lower dose of amphotericin B. Amphotericin B may also facilitate entry of flucystosine into the fungal cell by interfering with the permeability of the fungal cell membrane.
6242:
1548:
Its complete stereo structure was determined in 1970 by an X-ray structure of the N-iodoacetyl derivative. The first synthesis of the compound's naturally occurring enantiomeric form was achieved in 1987 by
3353:
J. Czub, M. Baginski. Amphotericin B and Its New
Derivatives Mode of action. Department of pharmaceutical Technology and Biochemistry. Faculty of Chemistry, Gdnsk University of Technology. 2009, 10-459-469.
1304:
fungal cell wall, but is not affected by the mammalian cell membrane, so the association with liposomes decreases the exposure of the kidneys to amphotericin B, which explains its less nephrotoxic effects.
1233:
However, recently novel nanoparticulate drug delivery systems such as AmbiOnp, nanosuspensions, lipid-based drug delivery systems including cochleates, self-emulsifying drug delivery systems, solid lipid
2772:
Italia JL, Yahya MM, Singh D, Ravi Kumar MN (June 2009). "Biodegradable nanoparticles improve oral bioavailability of amphotericin B and show reduced nephrotoxicity compared to intravenous
Fungizone".
968:
in the pathogens it treats. This is because amphotericin B resistance requires sacrifices on the part of the pathogen that make it susceptible to the host environment, and too weak to cause infection.
1945:
Moen MD, Lyseng-Williamson KA, Scott LJ (2012-09-17). "Liposomal amphotericin B: a review of its use as empirical therapy in febrile neutropenia and in the treatment of invasive fungal infections".
1993:
6235:
3097:
Gigliotti F, Shenep JL, Lott L, Thornton D (November 1987). "Induction of prostaglandin synthesis as the mechanism responsible for the chills and fever produced by infusing amphotericin B".
2612:
Wasan KM, Wasan EK, Gershkovich P, Zhu X, Tidwell RR, Werbovetz KA, et al. (August 2009). "Highly effective oral amphotericin B formulation against murine visceral leishmaniasis".
6742:
6228:
1424:
Transfusion of leukocytes: Risk of pulmonal (lung) damage occurs, space the intervals between the application of amphotericin B and the transfusion, and monitor pulmonary function
4094:
175:
3253:"Liposomal amphotericin B for empirical therapy in patients with persistent fever and neutropenia. National Institute of Allergy and Infectious Diseases Mycoses Study Group"
2591:
5754:
2116:
3173:
Baronti R, Masini E, Bacciottini L, Mannaioni PF (May 2002). "Differential effects of amphotericin B and liposomal amphotericin B on inflammatory cells in vitro".
73:
1496:
Amphotericin B administration is limited by infusion-related toxicity. This is thought to result from innate immune production of proinflammatory cytokines.
757:
3216:
Goodwin SD, Cleary JD, Walawander CA, Taylor JW, Grasela TH (April 1995). "Pretreatment regimens for adverse events related to infusion of amphotericin B".
1898:
2559:
1484:. Amphotericin A is almost identical to amphotericin B (having a C=C double bond between the 27th and 28th carbons), but has little antifungal activity.
429:)- 33-- 1,3,5,6,9,11,17,37-octahydroxy- 15,16,18-trimethyl- 13-oxo- 14,39-dioxabicyclo nonatriaconta- 19,21,23,25,27,29,31-heptaene- 36-carboxylic acid
6697:
4087:
1989:
1566:
formulation (LAMB). The latter formulations have been developed to improve tolerability and decrease toxicity, but may show considerably different
6737:
1533:, in 1955, at the Squibb Institute for Medical Research from cultures of an undescribed streptomycete isolated from the soil collected in the
6186:
5747:
5698:
4982:
4926:
3341:
1929:
1461:
within the fungal cell, but it remains unclear to what extent this oxidative damage contributes to the drug's effectiveness. The addition of
920:
4080:
1296:
have all been used to treat or prevent the syndrome, but the prophylactic use of these drugs is often limited by the patient's condition.
1817:
5979:
3072:
1478:
Two amphotericins, amphotericin A and amphotericin B, are known, but only B is used clinically, because it is significantly more active
985:
1602:
3805:
3665:
3294:"Clinical practice guidelines for the management of cryptococcal disease: 2010 update by the infectious diseases society of america"
1842:
1811:
1759:
1680:
1214:
nature of amphotericin along with its low solubility and permeability has posed major hurdles for oral administration given its low
777:
5740:
3134:"The antifungal drug amphotericin B promotes inflammatory cytokine release by a Toll-like receptor- and CD14-dependent mechanism"
3363:
Zietse R, Zoutendijk R, Hoorn EJ (April 2009). "Fluid, electrolyte and acid-base disorders associated with antibiotic therapy".
2583:
1715:
1628:
50:
6732:
4359:
337:
235:
105:
5465:
1784:
2649:"Clinical practice guidelines for the management of candidiasis: 2009 update by the Infectious Diseases Society of America"
6707:
5032:
3491:"Exposure of the yeast Candida albicans to the anti-neoplastic agent adriamycin increases the tolerance to amphotericin B"
124:
6662:
4043:
1892:
1198:
523:
2701:
Patel PA, Patravale VB (October 2011). "AmbiOnp: solid lipid nanoparticles of amphotericin B for oral administration".
6203:
5715:
4943:
3540:
1388:
941:
623:
3340:
Jill Adler-Moore,* and
Richard T. liposomal formulation, structure, mechanism of action and pre-clinical experience.
964:
infections. It has been a highly effective drug for over fifty years in large part because it has a low incidence of
1299:
Intravenously administered amphotericin B in therapeutic doses has also been associated with multiple organ damage.
4791:
4142:
3863:"Amphotericin biosynthesis in Streptomyces nodosus: deductions from analysis of polyketide synthase and late genes"
5533:
5503:
4975:
1858:
1737:
1658:
4014:
1886:
1585:
It is commercially known as
Fungilin, Fungizone, Abelcet, AmBisome, Fungisome, Amphocil, Amphotec, and Halizon.
6712:
5398:
4420:
4194:
2551:
1471:
1336:
965:
4702:
1990:"Understanding the evolution of drug resistance points to novel strategy for developing better antimicrobials"
1663:
Control of the leishmaniasis: report of a meeting of the WHO Expert
Committee on the Control of Leishmaniases
6643:
6191:
5801:
5703:
5633:
4931:
4865:
4179:
2208:
1086:
161:
662:
6717:
6415:
6352:
6147:
5929:
5670:
5317:
4736:
4711:
4508:
2325:"Comparison of fungizone, Amphotec, AmBisome, and Abelcet for treatment of systemic murine cryptococcosis"
996:
The following table shows the amphotericin B susceptibility for a selection of medically important fungi.
981:
592:
6722:
6433:
6086:
5937:
5933:
4887:
4623:
4519:
4514:
1014:
816:
1149:. As the original formulation of amphotericin, it is often referred to as "conventional" amphotericin.
6220:
5732:
944:. Due to its extensive side effects, it is often reserved for severe infections in critically ill, or
6702:
5847:
4968:
4639:
4174:
3406:
2154:
Hamill RJ (June 2013). "Amphotericin B formulations: a comparative review of efficacy and toxicity".
1522:
1174:
1162:
977:
903:
288:
168:
3622:
Laniado-LaborĂn R, Cabrales-Vargas MN (December 2009). "Amphotericin B: side effects and toxicity".
3292:
Perfect JR, Dismukes WE, Dromer F, Goldman DL, Graybill JR, Hamill RJ, et al. (February 2010).
6548:
5987:
5968:
5918:
5460:
5276:
4478:
3943:
Nicolaou KC, Daines RA, Chakraborty TK, Ogawa Y (1987-04-01). "Total synthesis of amphotericin B".
3737:
2887:
Boulware DR, Atukunda M, Kagimu E, Musubire AK, Akampurira A, Tugume L, et al. (August 2023).
1505:
1320:
1166:
1146:
1026:
891:
639:
438:
5831:
2110:
2108:
2106:
2104:
2102:
1351:
Drug-drug interactions may occur when amphotericin B is coadministered with the following agents:
612:
6377:
5792:
5623:
5593:
5588:
4587:
3783:
3647:
3521:
3388:
3198:
3036:
2797:
2647:
Pappas PG, Kauffman CA, Andes D, Benjamin DK, Calandra TF, Edwards JE, et al. (March 2009).
2533:
2425:"Does lipid emulsion reduce amphotericin B nephrotoxicity? A systematic review and meta-analysis"
2179:
2039:
1970:
1253:
1181:
in 1999). It was approved by the FDA in 1997. It is marketed by Gilead in Europe and licensed to
1098:
1074:
924:
844:
840:
135:
6049:
3251:
Walsh TJ, Finberg RW, Arndt C, Hiemenz J, Schwartz C, Bodensteiner D, et al. (March 1999).
2889:"Oral Lipid Nanocrystal Amphotericin B for Cryptococcal Meningitis: A Randomized Clinical Trial"
765:
O=C(O)3(O)C2(O)C(O)C(O)(O)CC(O)C(O)CC(=O)O(C)(C)(O)(C)C=CC=CC=CC=CC=CC=CC=C(O1O(C)(O)(N)1O)C3O2
6727:
5954:
5484:
4397:
4274:
4219:
4184:
3960:
3925:
3884:
3775:
3718:
3639:
3601:
3563:
3513:
3471:
3380:
3323:
3274:
3233:
3190:
3155:
3114:
3018:
2969:
2920:
2846:
2789:
2754:
2718:
2680:
2629:
2525:
2487:
2446:
2405:
2354:
2305:
2251:
2171:
2088:
2031:
1962:
1925:
1838:
1832:
1807:
1801:
1780:
1755:
1676:
1186:
1125:
945:
512:
63:
3061:
1323:) are common. In the circulatory system, several forms of anemia and other blood dyscrasias (
572:
5628:
5578:
4858:
4808:
4264:
4199:
4147:
3952:
3915:
3874:
3824:
3816:
3767:
3710:
3631:
3593:
3555:
3505:
3461:
3451:
3372:
3313:
3305:
3264:
3225:
3182:
3145:
3106:
3008:
3000:
2959:
2951:
2910:
2900:
2836:
2828:
2781:
2746:
2710:
2670:
2660:
2621:
2517:
2477:
2436:
2395:
2385:
2344:
2336:
2295:
2243:
2163:
2078:
2070:
2023:
1954:
1866:
1745:
1666:
1567:
1458:
1391:: Amphotericin B-induced hypokalemia may potentiate the effects of certain paralytic agents.
1218:. In the past it had been used for fungal infections of the surface of the GI tract such as
1142:
1050:
1038:
679:
260:
3584:
Baginski M, Czub J (June 2009). "Amphotericin B and its new derivatives - mode of action".
3440:"It only takes one to do many jobs: Amphotericin B as antifungal and immunomodulatory drug"
2938:
Carr JR, Hawkins WA, Newsome AS, Smith SE, Amber BC, Bland CM, et al. (October 2022).
2508:
Slain D (March 1999). "Lipid-based amphotericin B for the treatment of fungal infections".
1161:
AmBisome (liposomal amphotericin B; LAMB) is a liposomal formulation of amphotericin B for
532:
447:
6692:
6676:
6632:
6294:
6284:
6117:
6071:
5210:
5200:
4882:
4818:
4137:
3834:
2466:"Editorial response: choosing amphotericin B formulations-between a rock and a hard place"
1340:
1289:
1215:
1182:
1178:
871:
278:
268:
3676:
2374:"Amphotericin B deoxycholate versus liposomal amphotericin B: effects on kidney function"
1418:
Other nephrotoxic drugs (such as aminoglycosides): Increased risk of serious renal damage
3490:
2915:
2888:
2400:
2373:
666:
643:
17:
6587:
6372:
6362:
6254:
6197:
6125:
6094:
6023:
5881:
5873:
5858:
5823:
5709:
5640:
5583:
5553:
5538:
5195:
4937:
4754:
4659:
4593:
4524:
4401:
4390:
4289:
4284:
4103:
3466:
3439:
3318:
3293:
3013:
2988:
2964:
2939:
2841:
2816:
2675:
2648:
2083:
2058:
1550:
1438:
1368:
1316:
1312:
1300:
1293:
1197:
A number of lipid complex preparations are also available. Abelcet was approved by the
1062:
953:
848:
3879:
3862:
2349:
2324:
2247:
2014:
den Boer M, Davidson RN (April 2006). "Treatment options for visceral leishmaniasis".
1711:
1177:
that contain amphotericin B. It was developed by NeXstar
Pharmaceuticals (acquired by
83:
6686:
6649:
6500:
6490:
6450:
6423:
6405:
6271:
6129:
6102:
6037:
6027:
5910:
5783:
5763:
5543:
5439:
5413:
5220:
5172:
5138:
5093:
5063:
4824:
4776:
4707:
4437:
4308:
4298:
4229:
4061:
4049:
2865:
2300:
2283:
1958:
1534:
1173:
and distearoyl phosphatidylglycerol that in aqueous media spontaneously arrange into
957:
907:
in 1955 at the Squibb For
Medical Research Institute from cultures isolated from the
895:
856:
836:
832:
824:
744:
655:
97:
4072:
3787:
3525:
3392:
2817:"Stealth Amphotericin B nanoparticles for oral drug delivery: In vitro optimization"
2537:
2043:
1974:
6627:
6617:
6520:
6505:
6485:
6455:
6387:
6262:
6153:
6143:
6063:
6053:
5885:
5862:
5813:
5774:
5665:
5650:
5563:
5493:
5409:
5243:
5238:
5230:
5225:
5215:
5205:
5123:
5113:
5108:
5098:
5083:
5073:
5058:
4999:
4995:
4907:
4801:
4761:
4644:
4540:
4493:
4405:
4269:
4254:
4189:
4107:
3202:
2801:
2390:
2183:
1519:
1462:
1378:
1328:
1235:
949:
890:. There is a lipid formulation that has a lower risk of side effects. It is in the
828:
603:
218:
213:
208:
203:
198:
193:
188:
183:
3651:
2750:
1437:, a component of fungal cell membranes, forming pores that cause rapid leakage of
472:
41:
4038:
1421:
Cytostatic drugs: Increased risk of kidney damage, hypotension, and bronchospasms
6538:
6515:
6510:
6495:
6480:
6475:
6400:
6395:
6367:
6309:
6304:
6299:
6251:
6167:
6157:
6134:
6098:
6041:
5958:
5948:
5944:
5841:
5837:
5827:
5684:
5645:
5603:
5573:
5474:
5418:
5354:
5342:
5190:
5182:
5177:
5148:
5143:
5133:
5128:
5103:
5078:
4839:
4727:
4649:
4483:
4453:
4344:
4339:
4334:
4259:
4239:
4224:
4204:
4119:
3269:
3252:
3132:
Sau K, Mambula SS, Latz E, Henneke P, Golenbock DT, Levitz SM (September 2003).
2521:
1579:
1466:
1398:
1355:
1343:
have been reported. Skin reactions, including serious forms, are also possible.
1332:
1308:
1281:
1249:
1227:
1219:
1211:
1170:
961:
883:
879:
875:
852:
91:
3920:
3903:
3635:
3597:
3229:
3110:
2832:
2423:
Mistro S, Maciel I, de Menezes RG, Maia ZP, Schooley RT, BadarĂł R (June 2012).
33:
6637:
6607:
6582:
6470:
6460:
6357:
6314:
6289:
6279:
6258:
6106:
6075:
6059:
6031:
6015:
5895:
5891:
5674:
5655:
5618:
5613:
5598:
5568:
5548:
5513:
5433:
5428:
5423:
5384:
5363:
5328:
5281:
5118:
5068:
5053:
5017:
4991:
4912:
4902:
4897:
4834:
4829:
4786:
4781:
4771:
4732:
4561:
4534:
4498:
4394:
4348:
4234:
4214:
4161:
3996:
Christine D. Waugh, in xPharm: The Comprehensive Pharmacology Reference, 2007.
3771:
3559:
2955:
2785:
2234:
Dutcher JD (October 1968). "The discovery and development of amphotericin B".
2167:
1542:
1434:
1412:
1409:: Risk of hematological and renal side effects of amphotericin B are increased
1382:
1374:
1324:
1277:
1121:
709:
503:
3964:
3541:"Molecular modeling of amphotericin B-ergosterol primary complex in water II"
3456:
2027:
6622:
6561:
6465:
6442:
6343:
6333:
6006:
5819:
5809:
5660:
5608:
5337:
5296:
5262:
5088:
5044:
4960:
4717:
4692:
4634:
4606:
4577:
4571:
4555:
4545:
4488:
4463:
4458:
4324:
4244:
4157:
4127:
1538:
1530:
1442:
1402:
1394:
1362:
1285:
1273:
940:
One of the main uses of amphotericin B is treating a wide range of systemic
916:
887:
867:
310:
77:
3929:
3888:
3779:
3643:
3605:
3567:
3517:
3475:
3384:
3376:
3327:
3278:
3194:
3159:
3150:
3133:
3022:
2973:
2924:
2850:
2793:
2758:
2722:
2684:
2633:
2529:
2491:
2450:
2409:
2309:
2175:
2092:
2035:
1966:
1863:
World Health Organization model list of essential medicines: 21st list 2019
3804:
McNamara C, Crawforth J, Hickman B, Norwood T, Rawlings B (January 1998).
3722:
3509:
3237:
3118:
2905:
2714:
2358:
2255:
6556:
6530:
6163:
5964:
5770:
5767:
5558:
5301:
5253:
5163:
4766:
4687:
4676:
4672:
4614:
4473:
4468:
4448:
4303:
4249:
3004:
2441:
2424:
2340:
2115:
European Committee on Antimicrobial Susceptibility Testing (2015-11-16).
2074:
1563:
1454:
1450:
1406:
1265:
1261:
1223:
1145:
to improve solubility. Amphotericin B deoxycholate (ABD) is administered
483:
119:
3956:
3714:
1871:
492:
6612:
6324:
5851:
5679:
5291:
4682:
4619:
4329:
4209:
4132:
3186:
2815:
Al-Quadeib BT, Radwan MA, Siller L, Horrocks B, Wright MC (July 2015).
1750:
1671:
1629:"Ambisome- amphotericin b injection, powder, lyophilized, for solution"
1480:
1269:
912:
820:
458:
3829:
4663:
4629:
4116:
4006:
3820:
2696:
2694:
1446:
1257:
583:
3755:
3309:
2665:
2625:
2482:
2465:
2059:"Naegleria fowleri: pathogenesis, diagnosis, and treatment options"
552:
5028:
4892:
1527:
863:
732:
723:
563:
3902:
ProcĂłpio RE, Silva IR, Martins MK, Azevedo JL, AraĂşjo JM (2012).
2200:
2117:"Antifungal Agents, Breakpoint tables for interpretation of MICs"
1185:(formerly Fujisawa Pharmaceuticals) for marketing in the US, and
886:(inflammation of the heart). It appears to be relatively safe in
543:
6224:
5736:
4964:
4363:
4076:
894:
class of medications and works in part by interfering with the
244:
114:
4039:
AmBisome Summaries of Product Characteristics (United Kingdom)
3978:"Chemistry and Biology of the Polyene Macrolide Antibiotics".
3861:
Caffrey P, Lynch S, Flood E, Finnan S, Oliynyk M (July 2001).
1469:
can lead to amphotericin resistance in some species, such as
3756:"A labile point in mutant amphotericin polyketide synthases"
1603:"Updates to the Prescribing Medicines in Pregnancy database"
1365:: Increased renal toxicity and increased risk of hypokalemia
1210:
An oral preparation exists but is not widely available. The
628:
1922:
Drugs Active against Fungi, Pneumocystis, and Microsporidia
1665:. Geneva: World Health Organization. pp. 55, 88, 186.
1385:. The clinical significance of this interaction is unknown.
1315:
are also common. In the liver, increased liver enzymes and
1129:
948:
patients. It is considered first line therapy for invasive
318:
40% found in urine after single cumulated over several days
146:
2195:
2193:
1570:
characteristics compared to conventional amphotericin B.
2989:"Tolerability profile of the current antifungal armoury"
2201:"Index | The Antimicrobial Index Knowledgebase - TOKU-E"
1875:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
3617:
3615:
921:
World Health Organization's List of Essential Medicines
802:
3813:
Journal of the Chemical Society, Perkin Transactions 1
2372:
Botero Aguirre JP, Restrepo Hamid AM (November 2015).
1806:. Springer Science & Business Media. p. 109.
1415:: Increased risk of renal and hematological toxicity .
6660:
3438:
Mesa-Arango AC, Scorzoni L, Zaragoza O (2012-01-01).
2940:"Fluid Stewardship of Maintenance Intravenous Fluids"
2864:
Patel PA, Fernandes CB, Pol AS, Patravale VB (2013).
2578:
2576:
1714:. The American Society of Health-System Pharmacists.
1222:, but has been replaced by other antifungals such as
827:. The fungal infections it is used to treat include
6600:
6575:
6547:
6529:
6441:
6432:
6414:
6386:
6342:
6323:
6270:
6116:
6085:
6014:
6005:
5978:
5909:
5872:
5800:
5791:
5782:
5526:
5502:
5483:
5459:
5452:
5397:
5376:
5353:
5327:
5316:
5275:
5252:
5162:
5043:
5027:
5016:
5007:
4875:
4850:
4746:
4658:
4604:
4429:
4413:
4317:
4283:
4156:
4115:
3433:
3431:
1803:
Trends and Changes in Drug Research and Development
1578:Amphotericin's name originates from the chemical's
743:
721:
708:
678:
673:
654:
622:
602:
582:
562:
542:
522:
502:
482:
457:
437:
328:
309:
287:
277:
267:
259:
234:
229:
174:
160:
134:
104:
90:
72:
62:
57:
3489:O'Keeffe J, Doyle S, Kavanagh K (December 2003).
2284:"History of the development of azole derivatives"
1924:. Elsevier Health Sciences. pp. 479–494.e4.
1920:Bennett JE, Dolin R, Blaser MJ (28 August 2014).
3799:
3797:
2277:
2275:
1777:FarmacologĂa y su proyecciĂłn a la clĂnica 13a ed
1377:: Amphotericin B may antagonize the activity of
919:and came into medical use in 1958. It is on the
471:
27:Antifungal and antiparasitaric chemical compound
3579:
3577:
2229:
2227:
2225:
1740:(2009). Stuart MC, Kouimtzi M, Hill SR (eds.).
870:soon after the medication is given, as well as
446:
3856:
3854:
2149:
2147:
2145:
2143:
2141:
2139:
2137:
2135:
878:may occur. Other serious side effects include
6743:World Health Organization essential medicines
6236:
5748:
4976:
4375:
4088:
3666:"Amphocin, amphotericin B for injection, USP"
2866:"Oral amphotericin B: challenges and avenues"
2503:
2501:
8:
3908:The Brazilian Journal of Infectious Diseases
3539:Baran M, Borowski E, Mazerski J (May 2009).
2057:Grace E, Asbill S, Virga K (November 2015).
1307:In addition, electrolyte imbalances such as
976:Amphotericin B is used for life-threatening
862:Common side effects include a reaction with
611:
123:
32:
3754:Khan N, Rawlings B, Caffrey P (June 2011).
2378:The Cochrane Database of Systematic Reviews
1239:clinical trial in cryptococcal meningitis.
252:In general: â„ž (Prescription only)
6438:
6243:
6229:
6221:
6011:
5797:
5788:
5755:
5741:
5733:
5456:
5324:
5040:
5024:
5013:
4983:
4969:
4961:
4382:
4368:
4360:
4095:
4081:
4073:
1744:. World Health Organization. p. 145.
1706:
1704:
1702:
1700:
1698:
1696:
1694:
1692:
851:. For certain infections it is given with
665:
642:
511:
68:Fungizone, Mysteclin-F, AmBisome and other
49:
40:
3919:
3878:
3828:
3465:
3455:
3317:
3268:
3149:
3012:
2993:The Journal of Antimicrobial Chemotherapy
2963:
2914:
2904:
2840:
2674:
2664:
2481:
2440:
2399:
2389:
2348:
2299:
2082:
1870:
1749:
1670:
1653:
1651:
1649:
531:
4062:"Amphotericin B Lipid Complex Injection"
3945:Journal of the American Chemical Society
3498:The Journal of Pharmacy and Pharmacology
1504:The natural route to synthesis includes
998:
6667:
2584:"Drugs@FDA: FDA Approved Drug Products"
2016:Expert Review of Anti-Infective Therapy
1887:"Competitive Generic Therapy Approvals"
1594:
782:
762:
638:
491:
342:
96:
3904:"Antibiotics produced by Streptomyces"
3071:. University of Wisconsin-Eau Claire.
2739:International Journal of Pharmaceutics
1837:. John Wiley & Sons. p. 477.
1607:Therapeutic Goods Administration (TGA)
656:
31:
3342:Journal of Antimicrobial Chemotherapy
3078:from the original on 20 December 2016
2987:Mourad A, Perfect JR (January 2018).
2329:Antimicrobial Agents and Chemotherapy
2323:Clemons KV, Stevens DA (April 1998).
2063:Antimicrobial Agents and Chemotherapy
1865:. Geneva: World Health Organization.
1141:The original formulation uses sodium
591:
571:
82:
7:
4050:"Amphotericin B Liposomal Injection"
2703:Journal of Biomedical Nanotechnology
217:
207:
197:
187:
4747:Intestinal anti-inflammatory agents
3624:Revista Iberoamericana de Micologia
3257:The New England Journal of Medicine
3138:The Journal of Biological Chemistry
2288:Clinical Microbiology and Infection
1475:, without affecting the cell wall.
986:primary amoebic meningoencephalitis
551:
462:
302:Second phase: approximately 15 days
3736:Drew RH, Kauffman CA, Thorner AR.
3099:The Journal of Infectious Diseases
2614:The Journal of Infectious Diseases
25:
4804:agents, excluding corticosteroids
3738:"Pharmacology of amphotericin B."
2248:10.1378/chest.54.Supplement_1.296
1901:from the original on 29 June 2023
1779:(in Spanish). Oteo. p. 966.
1517:It was originally extracted from
901:Amphotericin B was isolated from
6698:Antifungals for dermatologic use
6670:
3806:"Biosynthesis of amphotericin B"
2301:10.1111/j.1470-9465.2004.00841.x
2003:– via Whitehead Institute.
1959:10.2165/00003495-200969030-00010
1820:from the original on 2017-09-10.
1545:antifungals in the early 1980s.
1133:may have fewer adverse effects.
696:
690:
321:Biliary excretion also important
5466:thymidylate synthase inhibitors
4017:from the original on 2016-11-15
2594:from the original on 2014-08-13
2562:from the original on 2015-11-17
2211:from the original on 2015-11-09
1996:from the original on 2016-11-15
1831:Fischer J, Ganellin CR (2006).
1718:from the original on 2015-01-01
1371:: Increased risk of hypokalemia
911:obtained from the river bed of
790:Key:APKFDSVGJQXUKY-INPOYWNPSA-N
6738:Respiratory chemical irritants
3069:Chem 491, Chemistry Department
2870:Int. J. Pharm. Biosci. Technol
2391:10.1002/14651858.cd010481.pub2
874:. Allergic symptoms including
699:
684:
1:
4851:Antidiarrheal micro-organisms
3880:10.1016/S1074-5521(01)00046-1
2751:10.1016/j.ijpharm.2009.01.003
1834:Analogue-based Drug Discovery
1389:Neuromuscular-blocking agents
1202:approved by the FDA in 1996.
1165:and consists of a mixture of
3298:Clinical Infectious Diseases
3218:Clinical Infectious Diseases
2944:Journal of Pharmacy Practice
2893:Clinical Infectious Diseases
2821:Saudi Pharmaceutical Journal
2653:Clinical Infectious Diseases
2470:Clinical Infectious Diseases
2429:Clinical Infectious Diseases
1893:Food and Drug Administration
3416:. Sigma-Tau Pharmaceuticals
3270:10.1056/NEJM199903113401004
3062:"Studies on Amphotericin B"
2522:10.1592/phco.19.4.306.30934
2464:Bennett J (November 2000).
6759:
4693:Camphorated opium tincture
4430:Intestinal anti-infectives
4143:Sodium monofluorophosphate
3921:10.1016/j.bjid.2012.08.014
3636:10.1016/j.riam.2009.06.003
3598:10.2174/138920009788898019
3365:Nature Reviews. Nephrology
2833:10.1016/j.jsps.2014.11.004
2282:Maertens JA (March 2004).
1433:Amphotericin B binds with
1193:Lipid complex formulations
992:Spectrum of susceptibility
674:Chemical and physical data
6181:
5693:
5534:bromochlorosalicylanilide
5504:Aminoacyl tRNA synthetase
4921:
3772:10.1007/s10529-011-0538-3
3560:10.1016/j.bpc.2009.01.010
3444:Frontiers in Microbiology
2956:10.1177/08971900211008261
2786:10.1007/s11095-009-9841-2
2242:(Supplement_1): 296–298.
2168:10.1007/s40265-013-0069-4
1859:World Health Organization
1738:World Health Organization
1659:World Health Organization
859:(injection into a vein).
798:
773:
753:
749:170 °C (338 °F)
333:
48:
39:
4626:, known as Pepto-Bismol)
4421:Oral rehydration therapy
4195:Cetylpyridinium chloride
3457:10.3389/fmicb.2012.00286
3407:"Abelcet Package Insert"
3230:10.1093/clinids/20.4.755
3111:10.1093/infdis/156.5.784
2028:10.1586/14787210.4.2.187
1742:WHO Model Formulary 2008
1472:Scedosporium prolificans
1337:ventricular fibrillation
1187:Sumitomo Pharmaceuticals
1120:Amphotericin B alone is
1080:Intrinsically resistant
855:. It is typically given
18:Liposomal amphotericin B
6644:Lactobacillus fermentum
5930:Pentavalent antimonials
5802:African trypanosomiasis
4866:Saccharomyces boulardii
3980:Bacteriological Reviews
3867:Chemistry & Biology
3586:Current Drug Metabolism
2774:Pharmaceutical Research
2552:"Drug Approval Package"
1321:fulminant liver failure
1087:Cryptococcus neoformans
954:cryptococcal meningitis
923:. It is available as a
299:Initial phase: 24 hours
6733:Polyketide antibiotics
6353:Diiodohydroxyquinoline
5318:Squalene monooxygenase
5155:Systemic: ketoconazole
3377:10.1038/nrneph.2009.17
3151:10.1074/jbc.M306137200
2588:www.accessdata.fda.gov
2556:www.accessdata.fda.gov
2205:antibiotics.toku-e.com
1111:Available formulations
1007:MIC breakpoint (mg/L)
982:visceral leishmaniasis
5938:Sodium stibogluconate
5934:Meglumine antimoniate
5346:Systemic: terbinafine
4888:Bismuth subsalicylate
4624:bismuth subsalicylate
4520:Succinylsulfathiazole
4515:Phthalylsulfathiazole
3815:(thesis) (1): 83–88.
3760:Biotechnology Letters
3548:Biophysical Chemistry
3510:10.1211/0022357022359
3175:Inflammation Research
3041:TheFreeDictionary.com
2715:10.1166/jbn.2011.1332
2236:Diseases of the Chest
1988:Rura N (2013-10-29).
1488:Mechanism of toxicity
1375:Imidazole Antifungals
1319:(up to and including
1015:Aspergillus fumigatus
817:antifungal medication
249: WARNING Rx-only
6708:Antiprotozoal agents
5848:naphthalenesulfonate
5634:Whitfield's ointment
5461:Pyrimidine analogues
5277:Polyene antimycotics
4876:Other antidiarrheals
4330:Acetylsalicylic acid
4175:Benzoxonium chloride
3414:Leadiant Biosciences
2999:(suppl_1): i26–i32.
2341:10.1128/AAC.42.4.899
2075:10.1128/AAC.01293-15
1775:Velázquez L (1976).
1175:unilamellar vesicles
978:protozoan infections
904:Streptomyces nodosus
169:Intravenous infusion
4725:does not cross BBB:
3957:10.1021/ja00243a043
3715:10.1021/bi00281a024
3144:(39): 37561–37568.
2906:10.1093/cid/ciad440
1506:polyketide synthase
1429:Mechanism of action
1331:), serious cardiac
1167:phosphatidylcholine
1027:Aspergillus terreus
880:low blood potassium
36:
6208:Never to phase III
5720:Never to phase III
5624:tribromometacresol
5594:sodium thiosulfate
5589:selenium disulfide
5485:Mitotic inhibitors
4948:Never to phase III
3187:10.1007/pl00000302
3005:10.1093/jac/dkx446
2442:10.1093/cid/cis290
1800:Walker SR (2012).
1339:), and even frank
1099:Fusarium oxysporum
1075:Candida lusitaniae
925:generic medication
915:in that region of
845:coccidioidomycosis
6658:
6657:
6596:
6595:
6218:
6217:
6177:
6176:
6001:
6000:
5955:phosphorylcholine
5905:
5904:
5730:
5729:
5522:
5521:
5448:
5447:
5399:β-glucan synthase
5393:
5392:
5372:
5371:
5271:
5270:
4958:
4957:
4398:anti-inflammatory
4357:
4356:
4275:Tibezonium iodide
4220:Hydrogen peroxide
4185:Chlortetracycline
4148:Stannous fluoride
3709:(12): 2939–2944.
3504:(12): 1629–1633.
2899:(12): 1659–1667.
2435:(12): 1774–1777.
2294:(Suppl 1): 1–10.
2069:(11): 6677–6681.
1931:978-1-4557-4801-3
1108:
1107:
946:immunocompromised
942:fungal infections
821:fungal infections
819:used for serious
810:
809:
734:Interactive image
624:CompTox Dashboard
248:
150:
117:
16:(Redirected from
6750:
6675:
6674:
6673:
6666:
6588:Methylrosaniline
6439:
6245:
6238:
6231:
6222:
6012:
5798:
5789:
5757:
5750:
5743:
5734:
5629:undecylenic acid
5579:potassium iodide
5457:
5325:
5041:
5025:
5014:
4985:
4978:
4971:
4962:
4859:Escherichia coli
4819:Aminosalicylates
4809:Cromoglicic acid
4384:
4377:
4370:
4361:
4265:Sodium perborate
4200:Domiphen bromide
4097:
4090:
4083:
4074:
4069:
4057:
4026:
4025:
4023:
4022:
4003:
3997:
3994:
3988:
3987:
3975:
3969:
3968:
3951:(9): 2821–2822.
3940:
3934:
3933:
3923:
3899:
3893:
3892:
3882:
3858:
3849:
3848:
3846:
3845:
3839:
3833:. Archived from
3832:
3821:10.1039/A704545J
3810:
3801:
3792:
3791:
3766:(6): 1121–1126.
3751:
3745:
3744:
3733:
3727:
3726:
3697:
3691:
3690:
3688:
3687:
3681:
3675:. Archived from
3670:
3662:
3656:
3655:
3619:
3610:
3609:
3581:
3572:
3571:
3554:(2–3): 162–168.
3545:
3536:
3530:
3529:
3495:
3486:
3480:
3479:
3469:
3459:
3435:
3426:
3425:
3423:
3421:
3411:
3403:
3397:
3396:
3360:
3354:
3351:
3345:
3344:(2002) 49, 21–30
3338:
3332:
3331:
3321:
3289:
3283:
3282:
3272:
3248:
3242:
3241:
3213:
3207:
3206:
3170:
3164:
3163:
3153:
3129:
3123:
3122:
3094:
3088:
3087:
3085:
3083:
3077:
3066:
3057:
3051:
3050:
3048:
3047:
3037:"Shake and Bake"
3033:
3027:
3026:
3016:
2984:
2978:
2977:
2967:
2935:
2929:
2928:
2918:
2908:
2884:
2878:
2877:
2861:
2855:
2854:
2844:
2812:
2806:
2805:
2780:(6): 1324–1331.
2769:
2763:
2762:
2733:
2727:
2726:
2698:
2689:
2688:
2678:
2668:
2644:
2638:
2637:
2609:
2603:
2602:
2600:
2599:
2580:
2571:
2570:
2568:
2567:
2548:
2542:
2541:
2505:
2496:
2495:
2485:
2476:(5): 1164–1165.
2461:
2455:
2454:
2444:
2420:
2414:
2413:
2403:
2393:
2384:(11): CD010481.
2369:
2363:
2362:
2352:
2320:
2314:
2313:
2303:
2279:
2270:
2266:
2260:
2259:
2231:
2220:
2219:
2217:
2216:
2197:
2188:
2187:
2151:
2130:
2129:
2127:
2126:
2121:
2112:
2097:
2096:
2086:
2054:
2048:
2047:
2011:
2005:
2004:
2002:
2001:
1985:
1979:
1978:
1942:
1936:
1935:
1917:
1911:
1910:
1908:
1906:
1897:. 29 June 2023.
1883:
1877:
1876:
1874:
1855:
1849:
1848:
1828:
1822:
1821:
1797:
1791:
1790:
1772:
1766:
1765:
1753:
1734:
1728:
1727:
1725:
1723:
1712:"Amphotericin B"
1708:
1687:
1686:
1674:
1655:
1644:
1643:
1641:
1639:
1625:
1619:
1618:
1616:
1614:
1599:
1459:oxidative stress
1051:Candida glabrata
1039:Candida albicans
999:
806:
805:
736:
716:
701:
698:
692:
686:
669:
658:
647:
646:
632:
630:
615:
595:
575:
555:
535:
515:
495:
475:
465:
464:
450:
292:
246:
243:
221:
211:
201:
191:
148:
145:
127:
116:
113:
100:
86:
53:
44:
37:
35:
21:
6758:
6757:
6753:
6752:
6751:
6749:
6748:
6747:
6713:Gilead Sciences
6683:
6682:
6681:
6671:
6669:
6661:
6659:
6654:
6633:Povidone-iodine
6592:
6571:
6543:
6525:
6428:
6410:
6382:
6338:
6319:
6295:Oxytetracycline
6285:Chloramphenicol
6266:
6255:anti-infectives
6249:
6219:
6214:
6213:
6198:Clinical trials
6173:
6138:
6118:Dientamoebiasis
6112:
6081:
5997:
5974:
5901:
5868:
5855:
5793:Trypanosomiasis
5778:
5761:
5731:
5726:
5725:
5710:Clinical trials
5689:
5518:
5498:
5479:
5464:
5444:
5401:
5389:
5368:
5349:
5345:
5320:
5312:
5304:
5279:
5267:
5248:
5201:fosravuconazole
5158:
5034:
5033:lanosterol 14α-
5020:
5009:
5003:
4989:
4959:
4954:
4953:
4938:Clinical trials
4917:
4883:Albumin tannate
4871:
4846:
4755:corticosteroids
4742:
4660:Antipropulsives
4654:
4600:
4425:
4409:
4388:
4358:
4353:
4313:
4290:Glucocorticoids
4287:
4285:Corticosteroids
4279:
4152:
4138:Sodium fluoride
4111:
4101:
4060:
4048:
4035:
4030:
4029:
4020:
4018:
4005:
4004:
4000:
3995:
3991:
3977:
3976:
3972:
3942:
3941:
3937:
3901:
3900:
3896:
3860:
3859:
3852:
3843:
3841:
3837:
3808:
3803:
3802:
3795:
3753:
3752:
3748:
3735:
3734:
3730:
3699:
3698:
3694:
3685:
3683:
3679:
3668:
3664:
3663:
3659:
3621:
3620:
3613:
3583:
3582:
3575:
3543:
3538:
3537:
3533:
3493:
3488:
3487:
3483:
3437:
3436:
3429:
3419:
3417:
3409:
3405:
3404:
3400:
3362:
3361:
3357:
3352:
3348:
3339:
3335:
3291:
3290:
3286:
3263:(10): 764–771.
3250:
3249:
3245:
3215:
3214:
3210:
3172:
3171:
3167:
3131:
3130:
3126:
3096:
3095:
3091:
3081:
3079:
3075:
3064:
3059:
3058:
3054:
3045:
3043:
3035:
3034:
3030:
2986:
2985:
2981:
2937:
2936:
2932:
2886:
2885:
2881:
2863:
2862:
2858:
2814:
2813:
2809:
2771:
2770:
2766:
2735:
2734:
2730:
2700:
2699:
2692:
2646:
2645:
2641:
2611:
2610:
2606:
2597:
2595:
2582:
2581:
2574:
2565:
2563:
2550:
2549:
2545:
2510:Pharmacotherapy
2507:
2506:
2499:
2463:
2462:
2458:
2422:
2421:
2417:
2371:
2370:
2366:
2322:
2321:
2317:
2281:
2280:
2273:
2267:
2263:
2233:
2232:
2223:
2214:
2212:
2199:
2198:
2191:
2153:
2152:
2133:
2124:
2122:
2119:
2114:
2113:
2100:
2056:
2055:
2051:
2013:
2012:
2008:
1999:
1997:
1987:
1986:
1982:
1944:
1943:
1939:
1932:
1919:
1918:
1914:
1904:
1902:
1885:
1884:
1880:
1857:
1856:
1852:
1845:
1830:
1829:
1825:
1814:
1799:
1798:
1794:
1787:
1774:
1773:
1769:
1762:
1736:
1735:
1731:
1721:
1719:
1710:
1709:
1690:
1683:
1657:
1656:
1647:
1637:
1635:
1627:
1626:
1622:
1612:
1610:
1601:
1600:
1596:
1591:
1576:
1568:pharmacokinetic
1559:
1515:
1502:
1490:
1439:monovalent ions
1431:
1369:Corticosteroids
1349:
1341:cardiac failure
1290:diphenhydramine
1245:
1216:bioavailability
1208:
1195:
1183:Astellas Pharma
1179:Gilead Sciences
1155:
1139:
1118:
1113:
1005:Amphotericin B
994:
974:
966:drug resistance
938:
933:
898:of the fungus.
872:kidney problems
801:
799:
794:
791:
786:
781:
780:
769:
766:
761:
760:
739:
714:
704:
695:
689:
650:
626:
618:
598:
578:
558:
538:
518:
498:
478:
461:
453:
433:
430:
341:
340:
324:
305:
290:
269:Bioavailability
261:Pharmacokinetic
255:
225:
163:
156:
137:
130:
28:
23:
22:
15:
12:
11:
5:
6756:
6754:
6746:
6745:
6740:
6735:
6730:
6725:
6720:
6715:
6710:
6705:
6700:
6695:
6685:
6684:
6680:
6679:
6656:
6655:
6653:
6652:
6647:
6640:
6635:
6630:
6625:
6620:
6615:
6610:
6604:
6602:
6598:
6597:
6594:
6593:
6591:
6590:
6585:
6579:
6577:
6573:
6572:
6570:
6569:
6567:Amphotericin B
6564:
6559:
6553:
6551:
6545:
6544:
6542:
6541:
6535:
6533:
6527:
6526:
6524:
6523:
6518:
6513:
6508:
6503:
6498:
6493:
6488:
6483:
6478:
6473:
6468:
6463:
6458:
6453:
6447:
6445:
6436:
6430:
6429:
6427:
6426:
6420:
6418:
6412:
6411:
6409:
6408:
6403:
6398:
6392:
6390:
6384:
6383:
6381:
6380:
6375:
6373:Broxyquinoline
6370:
6365:
6363:Chlorquinaldol
6360:
6355:
6349:
6347:
6340:
6339:
6337:
6336:
6330:
6328:
6321:
6320:
6318:
6317:
6312:
6307:
6302:
6297:
6292:
6287:
6282:
6276:
6274:
6268:
6267:
6250:
6248:
6247:
6240:
6233:
6225:
6216:
6215:
6212:
6211:
6210:
6209:
6206:
6195:
6189:
6183:
6182:
6179:
6178:
6175:
6174:
6172:
6171:
6161:
6151:
6140:
6139:
6132:
6126:nitroimidazole
6122:
6120:
6114:
6113:
6111:
6110:
6095:nitroimidazole
6091:
6089:
6087:Trichomoniasis
6083:
6082:
6080:
6079:
6068:
6067:
6057:
6046:
6045:
6035:
6024:nitroimidazole
6020:
6018:
6009:
6003:
6002:
5999:
5998:
5996:
5995:
5992:Amphotericin B
5984:
5982:
5976:
5975:
5973:
5972:
5962:
5952:
5927:
5926:
5923:Amphotericin B
5915:
5913:
5907:
5906:
5903:
5902:
5900:
5899:
5889:
5882:nitroimidazole
5878:
5876:
5874:Chagas disease
5870:
5869:
5867:
5866:
5859:nitroimidazole
5856:
5845:
5835:
5817:
5806:
5804:
5795:
5786:
5780:
5779:
5764:Antiparasitics
5762:
5760:
5759:
5752:
5745:
5737:
5728:
5727:
5724:
5723:
5722:
5721:
5718:
5707:
5701:
5695:
5694:
5691:
5690:
5688:
5687:
5682:
5677:
5668:
5663:
5658:
5653:
5648:
5643:
5641:citronella oil
5637:
5636:
5631:
5626:
5621:
5616:
5611:
5606:
5601:
5596:
5591:
5586:
5584:salicylic acid
5581:
5576:
5571:
5566:
5561:
5556:
5554:crystal violet
5551:
5546:
5541:
5539:chlorophetanol
5536:
5530:
5528:
5524:
5523:
5520:
5519:
5517:
5516:
5509:
5507:
5500:
5499:
5497:
5496:
5489:
5487:
5481:
5480:
5478:
5477:
5470:
5468:
5454:
5450:
5449:
5446:
5445:
5443:
5442:
5437:
5431:
5426:
5421:
5416:
5405:
5403:
5395:
5394:
5391:
5390:
5388:
5387:
5380:
5378:
5374:
5373:
5370:
5369:
5367:
5366:
5359:
5357:
5351:
5350:
5348:
5347:
5340:
5333:
5331:
5322:
5314:
5313:
5311:
5310:
5307:amphotericin B
5299:
5294:
5287:
5285:
5273:
5272:
5269:
5268:
5266:
5265:
5258:
5256:
5250:
5249:
5247:
5246:
5241:
5234:
5233:
5228:
5223:
5218:
5213:
5208:
5203:
5198:
5196:fosfluconazole
5193:
5186:
5185:
5180:
5175:
5168:
5166:
5160:
5159:
5157:
5156:
5152:
5151:
5146:
5141:
5136:
5131:
5126:
5121:
5116:
5111:
5106:
5101:
5096:
5091:
5086:
5081:
5076:
5071:
5066:
5061:
5056:
5049:
5047:
5038:
5022:
5011:
5005:
5004:
4990:
4988:
4987:
4980:
4973:
4965:
4956:
4955:
4952:
4951:
4950:
4949:
4946:
4935:
4929:
4923:
4922:
4919:
4918:
4916:
4915:
4910:
4905:
4900:
4895:
4890:
4885:
4879:
4877:
4873:
4872:
4870:
4869:
4862:
4854:
4852:
4848:
4847:
4845:
4844:
4843:
4842:
4837:
4832:
4827:
4814:
4813:
4812:
4811:
4797:
4796:
4795:
4794:
4789:
4784:
4779:
4774:
4769:
4767:Hydrocortisone
4764:
4757:acting locally
4750:
4748:
4744:
4743:
4741:
4740:
4730:
4721:
4720:
4715:
4697:
4696:
4690:
4685:
4680:
4673:Opium tincture
4669:
4667:
4656:
4655:
4653:
4652:
4647:
4642:
4637:
4632:
4627:
4617:
4611:
4609:
4602:
4601:
4599:
4598:
4597:
4596:
4594:Broxyquinoline
4583:
4582:
4581:
4580:
4567:
4566:
4565:
4564:
4551:
4550:
4549:
4548:
4543:
4530:
4529:
4528:
4527:
4525:Sulfaguanidine
4522:
4517:
4504:
4503:
4502:
4501:
4496:
4491:
4486:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4444:Amphotericin B
4433:
4431:
4427:
4426:
4424:
4423:
4417:
4415:
4411:
4410:
4402:anti-infective
4391:Antidiarrheals
4389:
4387:
4386:
4379:
4372:
4364:
4355:
4354:
4352:
4351:
4342:
4337:
4332:
4327:
4321:
4319:
4315:
4314:
4312:
4311:
4306:
4304:Hydrocortisone
4301:
4295:
4293:
4281:
4280:
4278:
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4237:
4232:
4227:
4222:
4217:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4170:Amphotericin B
4166:
4164:
4154:
4153:
4151:
4150:
4145:
4140:
4135:
4130:
4124:
4122:
4113:
4112:
4106:preparations (
4104:Stomatological
4102:
4100:
4099:
4092:
4085:
4077:
4071:
4070:
4058:
4046:
4044:Amphotericin B
4041:
4034:
4033:External links
4031:
4028:
4027:
3998:
3989:
3970:
3935:
3914:(5): 466–471.
3894:
3873:(7): 713–723.
3850:
3793:
3746:
3728:
3692:
3657:
3611:
3592:(5): 459–469.
3573:
3531:
3481:
3427:
3398:
3371:(4): 193–202.
3355:
3346:
3333:
3310:10.1086/649858
3304:(3): 291–322.
3284:
3243:
3224:(4): 755–761.
3208:
3181:(5): 259–264.
3165:
3124:
3105:(5): 784–789.
3089:
3052:
3028:
2979:
2950:(5): 769–782.
2930:
2879:
2856:
2827:(3): 290–302.
2807:
2764:
2745:(1–2): 76–84.
2728:
2709:(5): 632–639.
2690:
2666:10.1086/596757
2659:(5): 503–535.
2639:
2626:10.1086/600105
2620:(3): 357–360.
2604:
2572:
2543:
2516:(3): 306–323.
2497:
2483:10.1086/317443
2456:
2415:
2364:
2335:(4): 899–902.
2315:
2271:
2261:
2221:
2189:
2162:(9): 919–934.
2131:
2098:
2049:
2022:(2): 187–197.
2006:
1980:
1953:(3): 361–392.
1937:
1930:
1912:
1878:
1850:
1843:
1823:
1812:
1792:
1785:
1767:
1760:
1729:
1688:
1681:
1661:(March 2010).
1645:
1620:
1593:
1592:
1590:
1587:
1575:
1572:
1558:
1555:
1551:K. C. Nicolaou
1514:
1511:
1501:
1498:
1489:
1486:
1465:scavengers or
1430:
1427:
1426:
1425:
1422:
1419:
1416:
1410:
1392:
1386:
1372:
1366:
1359:
1348:
1345:
1317:hepatotoxicity
1313:hypomagnesemia
1294:hydrocortisone
1244:
1241:
1207:
1204:
1194:
1191:
1158:deoxycholate.
1154:
1151:
1138:
1135:
1117:
1114:
1112:
1109:
1106:
1105:
1102:
1094:
1093:
1090:
1082:
1081:
1078:
1070:
1069:
1066:
1063:Candida krusei
1058:
1057:
1054:
1046:
1045:
1042:
1034:
1033:
1030:
1022:
1021:
1018:
1010:
1009:
1003:
993:
990:
973:
970:
956:, and certain
937:
934:
932:
929:
866:, chills, and
849:cryptococcosis
813:Amphotericin B
808:
807:
796:
795:
793:
792:
789:
787:
784:
776:
775:
774:
771:
770:
768:
767:
764:
756:
755:
754:
751:
750:
747:
741:
740:
738:
737:
729:
727:
719:
718:
712:
706:
705:
702:
693:
687:
682:
676:
675:
671:
670:
660:
652:
651:
649:
648:
635:
633:
620:
619:
617:
616:
608:
606:
600:
599:
597:
596:
588:
586:
580:
579:
577:
576:
568:
566:
560:
559:
557:
556:
548:
546:
540:
539:
537:
536:
528:
526:
520:
519:
517:
516:
508:
506:
500:
499:
497:
496:
488:
486:
480:
479:
477:
476:
468:
466:
455:
454:
452:
451:
443:
441:
435:
434:
432:
431:
344:
336:
335:
334:
331:
330:
326:
325:
323:
322:
319:
315:
313:
307:
306:
304:
303:
300:
296:
294:
285:
284:
281:
275:
274:
271:
265:
264:
257:
256:
254:
253:
250:
240:
238:
232:
231:
227:
226:
224:
223:
180:
178:
172:
171:
166:
164:administration
158:
157:
155:
154:
152:
142:
140:
132:
131:
129:
128:
125:Amphotericin_B
110:
108:
102:
101:
94:
88:
87:
80:
70:
69:
66:
60:
59:
55:
54:
46:
45:
34:Amphotericin B
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6755:
6744:
6741:
6739:
6736:
6734:
6731:
6729:
6726:
6724:
6721:
6719:
6718:Lipid methods
6716:
6714:
6711:
6709:
6706:
6704:
6701:
6699:
6696:
6694:
6691:
6690:
6688:
6678:
6668:
6664:
6651:
6650:Copper usnate
6648:
6646:
6645:
6641:
6639:
6636:
6634:
6631:
6629:
6626:
6624:
6621:
6619:
6616:
6614:
6611:
6609:
6606:
6605:
6603:
6599:
6589:
6586:
6584:
6581:
6580:
6578:
6574:
6568:
6565:
6563:
6560:
6558:
6555:
6554:
6552:
6550:
6546:
6540:
6537:
6536:
6534:
6532:
6528:
6522:
6519:
6517:
6514:
6512:
6509:
6507:
6504:
6502:
6501:Propenidazole
6499:
6497:
6494:
6492:
6491:Fenticonazole
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6472:
6469:
6467:
6464:
6462:
6459:
6457:
6454:
6452:
6451:Metronidazole
6449:
6448:
6446:
6444:
6440:
6437:
6435:
6431:
6425:
6424:Sulfatolamide
6422:
6421:
6419:
6417:
6413:
6407:
6406:Ascorbic acid
6404:
6402:
6399:
6397:
6394:
6393:
6391:
6389:
6388:Organic acids
6385:
6379:
6376:
6374:
6371:
6369:
6366:
6364:
6361:
6359:
6356:
6354:
6351:
6350:
6348:
6345:
6341:
6335:
6332:
6331:
6329:
6326:
6322:
6316:
6313:
6311:
6308:
6306:
6303:
6301:
6298:
6296:
6293:
6291:
6288:
6286:
6283:
6281:
6278:
6277:
6275:
6273:
6269:
6264:
6260:
6256:
6253:
6252:Gynecological
6246:
6241:
6239:
6234:
6232:
6227:
6226:
6223:
6207:
6205:
6202:
6201:
6199:
6196:
6193:
6190:
6188:
6185:
6184:
6180:
6169:
6165:
6162:
6159:
6155:
6152:
6149:
6145:
6142:
6141:
6136:
6133:
6131:
6130:Metronidazole
6127:
6124:
6123:
6121:
6119:
6115:
6108:
6104:
6103:Metronidazole
6100:
6096:
6093:
6092:
6090:
6088:
6084:
6077:
6073:
6072:aminoacridine
6070:
6069:
6065:
6061:
6058:
6055:
6051:
6048:
6047:
6043:
6039:
6038:benzimidazole
6036:
6033:
6029:
6028:Metronidazole
6025:
6022:
6021:
6019:
6017:
6013:
6010:
6008:
6004:
5993:
5989:
5986:
5985:
5983:
5981:
5977:
5970:
5966:
5963:
5960:
5956:
5953:
5950:
5946:
5943:
5942:
5941:
5939:
5935:
5931:
5924:
5920:
5917:
5916:
5914:
5912:
5911:Leishmaniasis
5908:
5897:
5893:
5890:
5887:
5883:
5880:
5879:
5877:
5875:
5871:
5864:
5860:
5857:
5853:
5849:
5846:
5843:
5839:
5836:
5833:
5829:
5825:
5821:
5818:
5815:
5811:
5808:
5807:
5805:
5803:
5799:
5796:
5794:
5790:
5787:
5785:
5784:Discicristata
5781:
5776:
5772:
5769:
5765:
5758:
5753:
5751:
5746:
5744:
5739:
5738:
5735:
5719:
5717:
5714:
5713:
5711:
5708:
5705:
5702:
5700:
5697:
5696:
5692:
5686:
5683:
5681:
5678:
5676:
5672:
5669:
5667:
5664:
5662:
5659:
5657:
5654:
5652:
5649:
5647:
5644:
5642:
5639:
5638:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5615:
5612:
5610:
5607:
5605:
5602:
5600:
5597:
5595:
5592:
5590:
5587:
5585:
5582:
5580:
5577:
5575:
5572:
5570:
5567:
5565:
5562:
5560:
5557:
5555:
5552:
5550:
5547:
5545:
5544:chlorphenesin
5542:
5540:
5537:
5535:
5532:
5531:
5529:
5525:
5515:
5511:
5510:
5508:
5505:
5501:
5495:
5491:
5490:
5488:
5486:
5482:
5476:
5472:
5471:
5469:
5467:
5462:
5458:
5455:
5453:Intracellular
5451:
5441:
5440:ibrexafungerp
5438:
5435:
5432:
5430:
5427:
5425:
5422:
5420:
5417:
5415:
5414:anidulafungin
5411:
5410:echinocandins
5407:
5406:
5404:
5400:
5396:
5386:
5382:
5381:
5379:
5375:
5365:
5361:
5360:
5358:
5356:
5352:
5344:
5341:
5339:
5335:
5334:
5332:
5330:
5326:
5323:
5319:
5315:
5308:
5303:
5300:
5298:
5295:
5293:
5289:
5288:
5286:
5283:
5278:
5274:
5264:
5260:
5259:
5257:
5255:
5251:
5245:
5242:
5240:
5236:
5235:
5232:
5229:
5227:
5224:
5222:
5221:oteseconazole
5219:
5217:
5214:
5212:
5211:isavuconazole
5209:
5207:
5204:
5202:
5199:
5197:
5194:
5192:
5188:
5187:
5184:
5181:
5179:
5176:
5174:
5173:efinaconazole
5170:
5169:
5167:
5165:
5161:
5154:
5153:
5150:
5147:
5145:
5142:
5140:
5139:sertaconazole
5137:
5135:
5132:
5130:
5127:
5125:
5122:
5120:
5117:
5115:
5112:
5110:
5107:
5105:
5102:
5100:
5097:
5095:
5094:fenticonazole
5092:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5067:
5065:
5064:chlormidazole
5062:
5060:
5057:
5055:
5051:
5050:
5048:
5046:
5042:
5039:
5036:
5030:
5026:
5023:
5019:
5015:
5012:
5006:
5001:
4997:
4993:
4986:
4981:
4979:
4974:
4972:
4967:
4966:
4963:
4947:
4945:
4942:
4941:
4939:
4936:
4933:
4930:
4928:
4925:
4924:
4920:
4914:
4911:
4909:
4906:
4904:
4901:
4899:
4896:
4894:
4891:
4889:
4886:
4884:
4881:
4880:
4878:
4874:
4868:
4867:
4863:
4861:
4860:
4856:
4855:
4853:
4849:
4841:
4838:
4836:
4833:
4831:
4828:
4826:
4825:Sulfasalazine
4823:
4822:
4821:
4820:
4816:
4815:
4810:
4807:
4806:
4805:
4803:
4799:
4798:
4793:
4792:Beclometasone
4790:
4788:
4785:
4783:
4780:
4778:
4777:Betamethasone
4775:
4773:
4770:
4768:
4765:
4763:
4760:
4759:
4758:
4756:
4752:
4751:
4749:
4745:
4738:
4734:
4731:
4729:
4726:
4723:
4722:
4719:
4716:
4713:
4709:
4708:Diphenoxylate
4706:
4704:
4699:
4698:
4694:
4691:
4689:
4686:
4684:
4681:
4678:
4674:
4671:
4670:
4668:
4665:
4661:
4657:
4651:
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4628:
4625:
4621:
4618:
4616:
4613:
4612:
4610:
4608:
4603:
4595:
4592:
4591:
4590:
4589:
4585:
4584:
4579:
4576:
4575:
4574:
4573:
4569:
4568:
4563:
4560:
4559:
4558:
4557:
4553:
4552:
4547:
4544:
4542:
4539:
4538:
4537:
4536:
4532:
4531:
4526:
4523:
4521:
4518:
4516:
4513:
4512:
4511:
4510:
4506:
4505:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4482:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4441:
4440:
4439:
4435:
4434:
4432:
4428:
4422:
4419:
4418:
4416:
4412:
4407:
4403:
4399:
4396:
4392:
4385:
4380:
4378:
4373:
4371:
4366:
4365:
4362:
4350:
4346:
4343:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4322:
4320:
4316:
4310:
4309:Triamcinolone
4307:
4305:
4302:
4300:
4299:Dexamethasone
4297:
4296:
4294:
4291:
4286:
4282:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4236:
4233:
4231:
4230:Metronidazole
4228:
4226:
4223:
4221:
4218:
4216:
4213:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4180:Chlorhexidine
4178:
4176:
4173:
4171:
4168:
4167:
4165:
4163:
4159:
4155:
4149:
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4125:
4123:
4121:
4118:
4114:
4109:
4105:
4098:
4093:
4091:
4086:
4084:
4079:
4078:
4075:
4067:
4063:
4059:
4055:
4051:
4047:
4045:
4042:
4040:
4037:
4036:
4032:
4016:
4012:
4008:
4002:
3999:
3993:
3990:
3985:
3981:
3974:
3971:
3966:
3962:
3958:
3954:
3950:
3946:
3939:
3936:
3931:
3927:
3922:
3917:
3913:
3909:
3905:
3898:
3895:
3890:
3886:
3881:
3876:
3872:
3868:
3864:
3857:
3855:
3851:
3840:on 2017-09-21
3836:
3831:
3826:
3822:
3818:
3814:
3807:
3800:
3798:
3794:
3789:
3785:
3781:
3777:
3773:
3769:
3765:
3761:
3757:
3750:
3747:
3743:. MA Waltham.
3742:
3739:
3732:
3729:
3724:
3720:
3716:
3712:
3708:
3704:
3696:
3693:
3682:on 2011-04-19
3678:
3674:
3667:
3661:
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3653:
3649:
3645:
3641:
3637:
3633:
3629:
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3607:
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3599:
3595:
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3574:
3569:
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3561:
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3553:
3549:
3542:
3535:
3532:
3527:
3523:
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3515:
3511:
3507:
3503:
3499:
3492:
3485:
3482:
3477:
3473:
3468:
3463:
3458:
3453:
3449:
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3441:
3434:
3432:
3428:
3415:
3408:
3402:
3399:
3394:
3390:
3386:
3382:
3378:
3374:
3370:
3366:
3359:
3356:
3350:
3347:
3343:
3337:
3334:
3329:
3325:
3320:
3315:
3311:
3307:
3303:
3299:
3295:
3288:
3285:
3280:
3276:
3271:
3266:
3262:
3258:
3254:
3247:
3244:
3239:
3235:
3231:
3227:
3223:
3219:
3212:
3209:
3204:
3200:
3196:
3192:
3188:
3184:
3180:
3176:
3169:
3166:
3161:
3157:
3152:
3147:
3143:
3139:
3135:
3128:
3125:
3120:
3116:
3112:
3108:
3104:
3100:
3093:
3090:
3074:
3070:
3063:
3056:
3053:
3042:
3038:
3032:
3029:
3024:
3020:
3015:
3010:
3006:
3002:
2998:
2994:
2990:
2983:
2980:
2975:
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2898:
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2890:
2883:
2880:
2875:
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2860:
2857:
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2848:
2843:
2838:
2834:
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2826:
2822:
2818:
2811:
2808:
2803:
2799:
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2791:
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2779:
2775:
2768:
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2760:
2756:
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2740:
2732:
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2724:
2720:
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2712:
2708:
2704:
2697:
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2691:
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2677:
2672:
2667:
2662:
2658:
2654:
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2640:
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2623:
2619:
2615:
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2593:
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2579:
2577:
2573:
2561:
2557:
2553:
2547:
2544:
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2535:
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2511:
2504:
2502:
2498:
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2222:
2210:
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2196:
2194:
2190:
2185:
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2177:
2173:
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2165:
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2157:
2150:
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2146:
2144:
2142:
2140:
2138:
2136:
2132:
2118:
2111:
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2107:
2105:
2103:
2099:
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2064:
2060:
2053:
2050:
2045:
2041:
2037:
2033:
2029:
2025:
2021:
2017:
2010:
2007:
1995:
1991:
1984:
1981:
1976:
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1968:
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1952:
1948:
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1900:
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1864:
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1854:
1851:
1846:
1844:9783527607495
1840:
1836:
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1827:
1824:
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1815:
1813:9789400926592
1809:
1805:
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1796:
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1771:
1768:
1763:
1761:9789241547659
1757:
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1707:
1705:
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1682:9789241209496
1678:
1673:
1668:
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1646:
1634:
1630:
1624:
1621:
1609:. 12 May 2022
1608:
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1573:
1571:
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1540:
1536:
1535:Orinoco River
1532:
1529:
1525:
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1521:
1512:
1510:
1507:
1499:
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1494:
1487:
1485:
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1396:
1393:
1390:
1387:
1384:
1380:
1376:
1373:
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1367:
1364:
1361:Diuretics or
1360:
1357:
1354:
1353:
1352:
1346:
1344:
1342:
1338:
1334:
1330:
1326:
1322:
1318:
1314:
1310:
1305:
1302:
1301:Kidney damage
1297:
1295:
1291:
1287:
1283:
1279:
1275:
1271:
1267:
1263:
1259:
1255:
1251:
1242:
1240:
1237:
1236:nanoparticles
1231:
1229:
1225:
1221:
1217:
1213:
1205:
1203:
1200:
1192:
1190:
1188:
1184:
1180:
1176:
1172:
1168:
1164:
1159:
1152:
1150:
1148:
1147:intravenously
1144:
1136:
1134:
1131:
1127:
1126:normal saline
1123:
1115:
1110:
1103:
1101:
1100:
1096:
1095:
1091:
1089:
1088:
1084:
1083:
1079:
1077:
1076:
1072:
1071:
1067:
1065:
1064:
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1059:
1055:
1053:
1052:
1048:
1047:
1043:
1041:
1040:
1036:
1035:
1031:
1029:
1028:
1024:
1023:
1019:
1017:
1016:
1012:
1011:
1008:
1004:
1001:
1000:
997:
991:
989:
987:
983:
979:
972:Antiprotozoal
971:
969:
967:
963:
959:
955:
951:
947:
943:
935:
930:
928:
926:
922:
918:
914:
910:
909:streptomycete
906:
905:
899:
897:
896:cell membrane
893:
889:
885:
881:
877:
873:
869:
865:
860:
858:
857:intravenously
854:
850:
846:
842:
838:
837:blastomycosis
834:
833:aspergillosis
830:
826:
825:leishmaniasis
822:
818:
814:
804:
797:
788:
783:
779:
772:
763:
759:
752:
748:
746:
745:Melting point
742:
735:
731:
730:
728:
725:
720:
713:
711:
707:
683:
681:
677:
672:
668:
664:
661:
659:
657:ECHA InfoCard
653:
645:
641:
640:DTXSID9022601
637:
636:
634:
625:
621:
614:
610:
609:
607:
605:
601:
594:
590:
589:
587:
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581:
574:
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569:
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554:
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541:
534:
530:
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525:
521:
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510:
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81:
79:
75:
71:
67:
65:
61:
58:Clinical data
56:
52:
47:
43:
38:
30:
19:
6723:Nephrotoxins
6642:
6628:Furazolidone
6618:Policresulen
6566:
6521:Flutrimazole
6506:Butoconazole
6486:Ketoconazole
6456:Clotrimazole
6416:Sulfonamides
6378:Oxyquinoline
6154:tetracycline
6144:oxyquinoline
6064:Furazolidone
6054:Nitazoxanide
5991:
5928:
5922:
5886:Benznidazole
5863:Fexinidazole
5832:Tryparsamide
5814:Eflornithine
5766:directed at
5666:tea tree oil
5651:lemon myrtle
5564:ethylparaben
5494:griseofulvin
5355:Benzylamines
5306:
5244:ravuconazole
5239:albaconazole
5231:voriconazole
5226:posaconazole
5216:itraconazole
5206:hexaconazole
5124:neticonazole
5114:luliconazole
5109:ketoconazole
5099:flutrimazole
5084:eberconazole
5074:clotrimazole
5059:butoconazole
4908:Racecadotril
4864:
4857:
4817:
4802:antiallergic
4800:
4762:Prednisolone
4753:
4737:+simethicone
4724:
4700:
4640:Crospovidone
4588:Oxyquinoline
4586:
4570:
4554:
4541:Nifuroxazide
4533:
4509:Sulfonamides
4507:
4494:Streptomycin
4443:
4436:
4270:Tetracycline
4255:Oxyquinoline
4190:Clotrimazole
4169:
4065:
4053:
4019:. Retrieved
4010:
4001:
3992:
3983:
3979:
3973:
3948:
3944:
3938:
3911:
3907:
3897:
3870:
3866:
3842:. Retrieved
3835:the original
3812:
3763:
3759:
3749:
3740:
3731:
3706:
3703:Biochemistry
3702:
3695:
3684:. Retrieved
3677:the original
3672:
3660:
3630:(4): 223–7.
3627:
3623:
3589:
3585:
3551:
3547:
3534:
3501:
3497:
3484:
3447:
3443:
3418:. Retrieved
3413:
3401:
3368:
3364:
3358:
3349:
3336:
3301:
3297:
3287:
3260:
3256:
3246:
3221:
3217:
3211:
3178:
3174:
3168:
3141:
3137:
3127:
3102:
3098:
3092:
3080:. Retrieved
3068:
3060:Hartsel SC.
3055:
3044:. Retrieved
3040:
3031:
2996:
2992:
2982:
2947:
2943:
2933:
2896:
2892:
2882:
2873:
2869:
2859:
2824:
2820:
2810:
2777:
2773:
2767:
2742:
2738:
2731:
2706:
2702:
2656:
2652:
2642:
2617:
2613:
2607:
2596:. Retrieved
2587:
2564:. Retrieved
2555:
2546:
2513:
2509:
2473:
2469:
2459:
2432:
2428:
2418:
2381:
2377:
2367:
2332:
2328:
2318:
2291:
2287:
2264:
2239:
2235:
2213:. Retrieved
2204:
2159:
2155:
2123:. Retrieved
2066:
2062:
2052:
2019:
2015:
2009:
1998:. Retrieved
1983:
1950:
1946:
1940:
1921:
1915:
1903:. Retrieved
1890:
1881:
1872:10665/325771
1862:
1853:
1833:
1826:
1802:
1795:
1776:
1770:
1741:
1732:
1720:. Retrieved
1662:
1636:. Retrieved
1632:
1623:
1611:. Retrieved
1606:
1597:
1584:
1582:properties.
1577:
1560:
1557:Formulations
1547:
1520:Streptomyces
1518:
1516:
1503:
1500:Biosynthesis
1495:
1491:
1479:
1477:
1470:
1467:antioxidants
1463:free radical
1432:
1379:ketoconazole
1350:
1347:Interactions
1329:thrombopenia
1306:
1298:
1246:
1243:Side effects
1232:
1209:
1196:
1160:
1156:
1143:deoxycholate
1140:
1137:Deoxycholate
1119:
1097:
1085:
1073:
1061:
1049:
1037:
1025:
1013:
1006:
995:
975:
952:infections,
950:mucormycosis
939:
931:Medical uses
908:
902:
900:
861:
829:mucormycosis
812:
811:
800:
604:NIAID ChemDB
593:ChEMBL267345
426:
422:
418:
414:
410:
406:
402:
398:
394:
390:
386:
382:
378:
374:
370:
366:
362:
358:
354:
350:
346:
289:Elimination
236:Legal status
230:Legal status
106:License data
29:
6703:Antifungals
6539:Terconazole
6516:Oxiconazole
6511:Omoconazole
6496:Azanidazole
6481:Tioconazole
6476:Isoconazole
6434:Antifungals
6401:Acetic acid
6396:Lactic acid
6368:Dequalinium
6346:derivatives
6310:Clindamycin
6305:Mepartricin
6300:Carfecillin
6272:Antibiotics
6259:antiseptics
6194:from market
6168:Paromomycin
6158:Doxycycline
6135:Secnidazole
6099:Carnidazole
6042:Albendazole
5969:Paromomycin
5959:Miltefosine
5949:Pentamidine
5945:benzamidine
5842:Pentamidine
5838:benzamidine
5828:Melarsoprol
5706:from market
5685:pentamidine
5646:lemon grass
5604:taurolidine
5574:polynoxylin
5475:flucytosine
5419:caspofungin
5343:terbinafine
5329:Allylamines
5191:fluconazole
5183:terconazole
5178:fluconazole
5149:tioconazole
5144:sulconazole
5134:oxiconazole
5129:omoconazole
5104:isoconazole
5079:croconazole
5037:inhibitors)
5035:demethylase
4992:Antifungals
4934:from market
4840:Balsalazide
4728:Eluxadoline
4695:(paregoric)
4650:Diosmectite
4645:Attapulgite
4622:(including
4605:Intestinal
4484:Polymyxin B
4479:Paromomycin
4454:Fidaxomicin
4438:Antibiotics
4414:Rehydration
4345:Epinephrine
4340:Benzydamine
4335:Becaplermin
4260:Polynoxylin
4240:Minocycline
4225:Mepartricin
4205:Doxycycline
4162:antiseptics
4120:prophylaxis
4066:MedlinePlus
4054:MedlinePlus
1751:10665/44053
1672:10665/44412
1528:filamentous
1399:ganciclovir
1356:Flucytosine
1335:(including
1333:arrhythmias
1309:hypokalemia
1282:Paracetamol
1250:hypotension
1228:fluconazole
1212:amphipathic
1171:cholesterol
1116:Intravenous
958:aspergillus
884:myocarditis
876:anaphylaxis
853:flucytosine
841:candidiasis
717: g·mol
663:100.014.311
329:Identifiers
92:MedlinePlus
64:Trade names
6687:Categories
6638:Protiofate
6608:Clodantoin
6583:Ciclopirox
6471:Ornidazole
6461:Miconazole
6443:Imidazoles
6358:Clioquinol
6315:Pentamycin
6290:Hachimycin
6280:Candicidin
6148:Iodoquinol
6107:Tinidazole
6076:Quinacrine
6060:nitrofuran
6050:thiazolide
6032:Tinidazole
6016:Giardiasis
5896:Nifurtimox
5892:nitrofuran
5675:atovaquone
5656:orange oil
5619:tolnaftate
5614:tolciclate
5599:sulbentine
5569:haloprogin
5549:ciclopirox
5514:tavaborole
5506:inhibitors
5492:Systemic:
5473:Systemic:
5434:rezafungin
5429:micafungin
5424:cilofungin
5408:Systemic:
5402:inhibitors
5385:amorolfine
5364:butenafine
5321:inhibitors
5305:Systemic:
5282:ergosterol
5189:Systemic:
5119:miconazole
5069:climbazole
5054:bifonazole
5045:Imidazoles
5021:inhibitors
5018:Ergosterol
4913:Kaopectate
4903:Octreotide
4898:Crofelemer
4835:Olsalazine
4830:Mesalazine
4787:Budesonide
4782:Tixocortol
4772:Prednisone
4733:Loperamide
4607:adsorbents
4562:Miconazole
4535:Nitrofuran
4499:Vancomycin
4395:intestinal
4349:Adrenalone
4235:Miconazole
4215:Hexetidine
4021:2016-11-14
3844:2018-05-16
3830:2381/33805
3686:2010-02-18
3082:8 December
3046:2016-12-09
2598:2015-11-03
2566:2015-11-03
2215:2015-11-17
2125:2015-11-17
2000:2016-11-14
1786:8485152050
1722:January 1,
1589:References
1580:amphoteric
1537:region of
1435:ergosterol
1413:Zidovudine
1383:miconazole
1325:leukopenia
1278:drowsiness
1189:in Japan.
1032:Resistant
936:Antifungal
722:3D model (
710:Molar mass
573:CHEBI:2682
533:7XU7A7DROE
504:ChemSpider
448:12633-72-6
439:CAS Number
338:IUPAC name
279:Metabolism
6623:Nifuratel
6562:Natamycin
6531:Triazoles
6466:Econazole
6344:Quinoline
6334:Acetarsol
6327:compounds
6204:Phase III
6192:Withdrawn
6164:neomycin
6007:Trichozoa
5820:arsenical
5810:ornithine
5771:parasites
5716:Phase III
5704:Withdrawn
5661:patchouli
5609:ticlatone
5512:Topical:
5383:Topical:
5362:Topical:
5338:naftifine
5336:Topical:
5309:, hamycin
5297:natamycin
5290:Topical:
5263:abafungin
5261:Topical:
5254:Thiazoles
5237:Unknown:
5171:Topical:
5164:Triazoles
5089:econazole
5052:Topical:
4944:Phase III
4932:Withdrawn
4893:Ceratonia
4718:Difenoxin
4712:+atropine
4578:Acetarsol
4572:Arsenical
4556:Imidazole
4546:Nifurzide
4489:Rifaximin
4464:Natamycin
4459:Kanamycin
4325:Amlexanox
4245:Natamycin
4158:Infection
4128:Dectaflur
4011:Edu.drugs
4007:"Halizon"
3965:0002-7863
2876:(1): 1–9.
1638:11 August
1564:liposomal
1539:Venezuela
1531:bacterium
1403:tenofovir
1395:Foscarnet
1363:cisplatin
1286:pethidine
1274:tachypnea
1163:injection
1153:Liposomal
1122:insoluble
917:Venezuela
888:pregnancy
868:headaches
311:Excretion
291:half-life
273:100% (IV)
162:Routes of
136:Pregnancy
84:Monograph
78:Drugs.com
6728:Polyenes
6677:Medicine
6557:Nystatin
6549:Polyenes
5965:neomycin
5768:excavata
5559:dimazole
5302:nystatin
5284:binding)
5010:membrane
4701:crosses
4688:Morphine
4677:laudanum
4615:Charcoal
4474:Nystatin
4469:Neomycin
4449:Colistin
4404:agents (
4250:Neomycin
4015:Archived
3930:22975171
3889:11451671
3788:10209476
3780:21267757
3741:UpToDate
3644:19836985
3606:19689243
3568:19233539
3526:38893122
3518:14738588
3476:23024638
3393:24486546
3385:19322184
3328:20047480
3279:10072411
3195:12056514
3160:12860979
3073:Archived
3023:29304209
2974:33827313
2925:37606364
2916:10724459
2851:26106277
2794:19214716
2759:19236839
2723:22195480
2685:19191635
2634:19545212
2592:Archived
2560:Archived
2538:43479677
2530:10221369
2492:11073746
2451:22491505
2410:26595825
2401:10542271
2310:14748798
2269:146-154.
2209:Archived
2176:23729001
2093:26259797
2044:42784356
2036:16597201
1994:Archived
1975:34340503
1967:19275278
1899:Archived
1861:(2019).
1818:Archived
1716:Archived
1633:DailyMed
1407:adefovir
1266:headache
1262:vomiting
1254:anorexia
1224:nystatin
1206:By mouth
1002:Species
980:such as
962:candidal
803:(verify)
513:10237579
484:DrugBank
176:ATC code
151: B2
138:category
120:DailyMed
6613:Inosine
6325:Arsenic
5988:polyene
5919:polyene
5852:Suramin
5680:dapsone
5292:hamycin
4683:Codeine
4664:opioids
4620:Bismuth
4210:Eugenol
4133:Olaflur
3723:6871175
3467:3441194
3450:: 286.
3420:14 July
3319:5826644
3238:7795069
3203:2124507
3119:3309074
3014:6636388
2965:8497650
2842:4475820
2802:8612917
2676:7294538
2359:9559804
2256:4877964
2184:2785865
2084:4604384
1905:29 June
1523:nodosus
1513:History
1481:in vivo
1270:dyspnea
913:Orinoco
892:polyene
715:924.091
680:Formula
493:DB00681
459:PubChem
216: (
214:J02AA01
206: (
204:G01AA03
196: (
194:A07AA07
192:)
186: (
184:A01AB04
122::
98:a682643
6693:Aldols
6663:Portal
6187:WHO-EM
5824:Atoxyl
5699:WHO-EM
5527:Others
5377:Others
5029:Azoles
4927:WHO-EM
4635:Kaolin
4630:Pectin
4117:Caries
3963:
3928:
3887:
3786:
3778:
3721:
3673:Pfizer
3652:592301
3650:
3642:
3604:
3566:
3524:
3516:
3474:
3464:
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3383:
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2849:
2839:
2800:
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2528:
2490:
2449:
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2357:
2350:105563
2347:
2308:
2254:
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2174:
2091:
2081:
2042:
2034:
1973:
1965:
1928:
1841:
1810:
1783:
1758:
1679:
1613:13 May
1292:, and
1258:nausea
1220:thrush
847:, and
815:is an
758:SMILES
613:000096
584:ChEMBL
553:D00203
283:kidney
118:
6601:Other
6576:Other
5008:Wall/
4318:Other
3838:(PDF)
3809:(PDF)
3784:S2CID
3680:(PDF)
3669:(PDF)
3648:S2CID
3544:(PDF)
3522:S2CID
3494:(PDF)
3410:(PDF)
3389:S2CID
3199:S2CID
3076:(PDF)
3065:(PDF)
2798:S2CID
2534:S2CID
2180:S2CID
2156:Drugs
2120:(PDF)
2040:S2CID
1971:S2CID
1947:Drugs
1895:(FDA)
1891:U.S.
1574:Names
1543:azole
1128:at a
864:fever
778:InChI
724:JSmol
564:ChEBI
473:14956
6257:and
4998:and
4400:and
4160:and
3961:ISSN
3926:PMID
3885:PMID
3776:PMID
3719:PMID
3640:PMID
3602:PMID
3564:PMID
3514:PMID
3472:PMID
3422:2022
3381:PMID
3324:PMID
3275:PMID
3234:PMID
3191:PMID
3156:PMID
3115:PMID
3084:2016
3019:PMID
2970:PMID
2921:PMID
2847:PMID
2790:PMID
2755:PMID
2719:PMID
2681:PMID
2630:PMID
2526:PMID
2488:PMID
2447:PMID
2406:PMID
2382:2015
2355:PMID
2306:PMID
2252:PMID
2172:PMID
2089:PMID
2032:PMID
1963:PMID
1926:ISBN
1907:2023
1839:ISBN
1808:ISBN
1781:ISBN
1756:ISBN
1724:2015
1677:ISBN
1640:2021
1615:2022
1526:, a
1453:and
1381:and
1311:and
1272:and
1226:and
984:and
960:and
882:and
823:and
544:KEGG
524:UNII
393:, 23
365:, 11
263:data
74:AHFS
6263:G01
5980:PAM
5775:P01
5671:PCP
5000:J02
4996:D01
4703:BBB
4406:A07
4108:A01
3953:doi
3949:109
3916:doi
3875:doi
3825:hdl
3817:doi
3768:doi
3711:doi
3632:doi
3594:doi
3556:doi
3552:141
3506:doi
3462:PMC
3452:doi
3373:doi
3314:PMC
3306:doi
3265:doi
3261:340
3226:doi
3183:doi
3146:doi
3142:278
3107:doi
3103:156
3009:PMC
3001:doi
2960:PMC
2952:doi
2911:PMC
2901:doi
2837:PMC
2829:doi
2782:doi
2747:doi
2743:372
2711:doi
2671:PMC
2661:doi
2622:doi
2618:200
2518:doi
2478:doi
2437:doi
2396:PMC
2386:doi
2345:PMC
2337:doi
2296:doi
2244:doi
2164:doi
2079:PMC
2071:doi
2024:doi
1955:doi
1867:hdl
1746:hdl
1667:hdl
1199:FDA
1124:in
629:EPA
463:CID
425:,37
421:,36
417:,35
413:,33
409:,31
405:,29
401:,27
397:,25
389:,21
385:,19
381:,18
377:,17
373:,16
369:,15
219:WHO
212:),
209:WHO
202:),
199:WHO
189:WHO
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