575:. They are best avoided in the athlete population. Safety concerns exist for fluoroquinolone use during pregnancy, so they are contraindicated unless no other safe alternative antibiotic exists. However, one meta-analysis looking at the outcome of pregnancies involving quinolone use in the first trimester found no increased risk of malformations. They are also contraindicated in children due to the risks of damage to the musculoskeletal system. Their use in children is not absolutely contraindicated, however for certain severe infections where other antibiotics are not an option, their use can be justified. Quinolones should also not be given to people with a known
1395:
effects occurring at the same time and causing the potential for irreversible impairment. The advisory committee concluded that the serious risks associated with the use of fluoroquinolones for these types of uncomplicated infections generally outweighed the benefits for patients with other treatment options. The 21-member joint committee overwhelmingly recommended stronger label warnings on the containers because of rare but sometimes devastating side effects.
195:
2930:"Information for Healthcare Professionals: Fluoroquinolone Antimicrobial Drugs [ciprofloxacin (Marketed as Cipro and generic ciprofloxacin), ciprofloxacin extended-release (Marketed as Cipro XR and Proquin XR), gemifloxacin (Marketed as Factive), levofloxacin (Marketed as Levaquin), moxifloxacin (Marketed as Avelox), norfloxacin (Marketed as Noroxin), and ofloxacin (Marketed as Floxin)]"
205:
51:
1343:
708:
1431:
1748:
277:
deaths were observed in the levofloxacin group, neither of which was thought to be treatment-related. Spontaneous reports to the U.S. FDA Adverse
Effects Reporting System at the time of the 20 September 2011 U.S. FDA Pediatric Drugs Advisory Committee included musculoskeletal events (39, including five cases of tendon rupture) and
723:, DNA gyrase and topoisomerase IV, which cut DNA to introduce supercoiling, while leaving nuclease activity unaffected. With the ligase activity disrupted, these enzymes release DNA with single- and double-strand breaks that lead to cell death. The majority of quinolones in clinical use are fluoroquinolones, which have a
329:
also may be higher among people who are male, have a pre-existing joint or tendon issue, have kidney disease, or are highly active. Some experts have advised avoidance of fluoroquinolones in athletes. If tendonitis occurs, it generally appears within one month, and the most common tendon injured appears to be the
1391:
the increased risk of tendinitis and tendon rupture. In
February 2011, the risk of worsening symptoms for those with myasthenia gravis was added to the warning. In August 2013, the agency required updates to the labels to describe the potential for irreversible peripheral neuropathy (serious nerve damage).
1398:
On 12 May 2016, the FDA issued a drug safety communication advising that fluoroquinolones should be reserved for these conditions only when no other options are available due to potentially permanent, disabling side effects occurring together. The drug safety communication also announced the required
1390:
These drugs were widely used as a first-line treatment for many infections, including very commons ones such as acute sinusitis, acute bronchitis, and uncomplicated UTIs. Reports of serious adverse events began emerging, and the FDA first added a black-box warning to fluoroquinolones in July 2008 for
276:
in 712 children with community-acquired pneumonia, serious adverse events were experienced by 6% of those treated with levofloxacin and 4% of those treated with comparator antibiotics. Most of these were considered by the treating physician to be unrelated or doubtfully related to the study drug. Two
255:
In most countries, fluoroquinolones are approved for use in children only under narrowly defined circumstances, owing in part to the observation of high rates of musculoskeletal adverse events in fluoroquinolone-treated juvenile animals. In the UK, the prescribing indications for fluoroquinolones for
1394:
In
November 2015, an FDA Advisory Committee discussed the risks and benefits of fluoroquinolones for the treatment of acute bacterial sinusitis, acute bacterial exacerbation of chronic bronchitis, and uncomplicated UTIs based on new safety information. The new information focused on two or more side
319:
were added in 2018. In
December 2018, the FDA issued a warning regarding an increased risk of aortic aneurysms and aortic dissections associated with fluoroquinolone use. This warning specifically targeted older adults and patients with conditions such as hypertension, Marfan syndrome, Ehlers-Danlos
4041:
From 1995 to 2002, inappropriate antibiotic prescribing for acute respiratory infections, which are usually caused by viruses and thus are not responsive to antibiotics, declined from 61 to 49 percent. However, the use of broad-spectrum antibiotics such as the fluoroquinolones, jumped from 41 to 77
1399:
labeling updates to reflect this new safety information. The FDA put out another label change in July 2017, strengthening the warnings about potentially disabling adverse effects and limiting use of these drugs to second-line treatments for acute sinusitis, acute bronchitis, and uncomplicated UTIs.
328:
Quinolones are associated with a small risk of tendonitis and tendon rupture; a 2013 review found the incidence of tendon injury among those taking fluoroquinolones to be between 0.08 and 0.20%. The risk appears to be higher among people older than 60 and those also taking corticosteroids; the risk
1447:
Quinolones can be classified into generations based on their antibacterial spectrums. The earlier-generation agents are, in general, more narrow-spectrum than the later ones, but no standard is employed to determine which drug belongs to which generation. The only universal standard applied is the
1434:
Sites of substitution in second-generation fluoroquinolone antibiotics: Here, and in following the orientation of the quinolones are flipped with respect to horizontal and vertical axes, relative to earlier images; the nitrogen (N)-containing pyridine ring is now on the left, and the N-1 atom and
404:
The overall rate of adverse events in people treated with fluoroquinolones is roughly similar to that seen in people treated with other antibiotic classes. A U.S. Centers for
Disease Control and Prevention study found people treated with fluoroquinolones experienced adverse events severe enough to
386:
More generally, fluoroquinolones are tolerated, with typical drug side effects being mild to moderate. Common side effects include gastrointestinal effects such as nausea, vomiting, and diarrhea, as well as headache and insomnia. Postmarketing surveillance has revealed a variety of relatively rare
740:
suffix. First and second generation quinolones are largely active against Gram-negative bacteria, whereas third and fourth generation quinolones have increased activity against Gram-positive and anaerobic bacteria. Some quinolones containing aromatic substituents at their C-7 positions are highly
310:
on all fluoroquinolones, advising of the increased risk of tendon damage. In 2016, the FDA found that systemic use (by mouth or injection) of fluoroquinolones was associated with "disabling and potentially permanent serious side effects" involving the tendons, muscles, joints, nerves, and central
400:
A 2018 EU-wide review of fluoroquinolones concluded that they are associated with serious side effects including tendonitis, tendon rupture, arthralgia, pain in extremities, gait disturbance, neuropathies associated with paraesthesia, depression, fatigue, memory impairment, sleep disorders, and
214:
Fluoroquinolones are often used for genitourinary infections and are widely used in the treatment of hospital-acquired infections associated with urinary catheters. In community-acquired infections, they are recommended only when risk factors for multidrug resistance are present or after other
629:
infections, treatment guidelines often recommend minimizing the use of fluoroquinolones and other broad-spectrum antibiotics in less severe infections and in those in which risk factors for multidrug resistance are not present. It has been recommended that fluoroquinolones not be used as a
373:
may occur in connection with the use of any antibacterial drug, especially those with a broad spectrum of activity such as clindamycin, cephalosporins, and fluoroquinolones. Fluoroquinoline treatment is associated with risk that is similar to or less than that associated with broad spectrum
787:
Eukaryotic cells are not believed to contain DNA gyrase or topoisomerase IV. However, debate exists concerning whether the quinolones still have such an adverse effect on the DNA of healthy cells. Some compounds in this class have been shown to inhibit the synthesis of
1407:
The first generation of the quinolones began following introduction of the related, but structurally distinct naphthyridine-family nalidixic acid in 1962 for treatment of UTIs in humans. Nalidixic acid was discovered by George Lesher and coworkers in a chemical
281:
events (19, including five cases of seizures) as the most common spontaneous reports between April 2005 and March 2008. An estimated 130,000 pediatric prescriptions for levofloxacin were filled on behalf of 112,000 pediatric patients during that period.
1370:
synthesis. Nalidixic acid is thus considered to be the predecessor of all members of the quinolone family, including the second, third and fourth generations commonly known as fluoroquinolones. Since the introduction of nalidixic acid, more than 10,000
744:
It has also been proposed that quinolone antibiotics cause oxidation of guanine nucleotides in the bacterial nucleotide pool, and that this process contributes to the cytotoxicity of these agents. The incorporation of oxidized guanine nucleotides into
401:
impaired hearing, vision, taste and smell. Tendon damage (especially to
Achilles tendon but also other tendons) can occur within 48 hours of starting fluoroquinolone treatment but the damage may be delayed several months after stopping treatment.
311:
nervous system, concluding that these side effects generally outweigh the benefits for people with acute sinusitis, acute bronchitis, and uncomplicated urinary tract infections when other treatment options are available. Concerns regarding
547:, so may have interactions with drugs cleared by those enzymes; the order from most P450-inhibitory to least, is enoxacin > ciprofloxacin > norfloxacin > ofloxacin, levofloxacin, trovafloxacin, gatifloxacin, moxifloxacin.
3060:
Falagas ME, Matthaiou DK, Vardakas KZ (December 2006). "Fluoroquinolones vs beta-lactams for empirical treatment of immunocompetent patients with skin and soft tissue infections: a meta-analysis of randomized controlled trials".
4652:
359:, and the elderly. For these people, fluoroquinolones should be used only when no other treatment options are available. One year after the warning announcement, prescribing behaviors were reported to have remained unchanged.
350:
Fluoroquinolones can increase the rate of rare but serious tears in the aorta by 31% compared to other antibiotics. People at increased risk include those with aortic aneurysm, hypertension, certain genetic conditions such as
804:, or active structure, of the fluoroquinolone class is based upon the quinoline ring system. Various substitutions made to the quinoline ring resulted in the development of numerous fluoroquinolone drugs. The addition of the
1752:
638:
Working Group recommends fluoroquinolones be used for the ambulatory treatment of community-acquired pneumonia only after other antibiotic classes have been tried and failed, or in cases with demonstrated drug-resistant
3581:
Noel GJ, Bradley JS, Kauffman RE, Duffy CM, Gerbino PG, Arguedas A, et al. (October 2007). "Comparative safety profile of levofloxacin in 2523 children with a focus on four specific musculoskeletal disorders".
285:
Meta-analyses conclude that fluoroquinolones pose little or no additional risk to children compared to other antibiotic classes. Fluoroquinolone use in children may be appropriate when the infection is caused by
4726:
4702:
2015:
American
Thoracic Society, Infectious Diseases Society of America (February 2005). "Guidelines for the management of adults with hospital-acquired, ventilator-associated, and healthcare-associated pneumonia".
341:
Nervous-system effects include insomnia, restlessness, and rarely, seizure, convulsions, and psychosis. Other rare and serious adverse events have been observed with varying degrees of evidence for causation.
1435:
C-6 carbonyl are at 12 o'clock and 6 o'clock in the pyridine ring. The characteristic 6-fluoro group is shown in red. For instance, in ciprofloxacin, above, the R substituent attached to the N-1 atom is a
5056:
4042:
percent from 1995 to 2001. Overuse of these antibiotics will eventually render them useless for treating antibiotic-resistant infections, for which broad-spectrum antibiotics are supposed to be reserved.
1420:
later.) The majority of quinolones in clinical use belong to the second generation class of "fluoroquinolones", which have a true quinoline framework, maintain the C-3 carboxylic acid group, and add a
4676:
2461:
Galatti L, Giustini SE, Sessa A, Polimeni G, Salvo F, Spina E, Caputi AP (March 2005). "Neuropsychiatric reactions to drugs: an analysis of spontaneous reports from general practitioners in Italy".
664:
Fluoroquinolones had become the class of antibiotics most commonly prescribed to adults in 2002. Nearly half (42%) of these prescriptions were for conditions not approved by the U.S. FDA, such as
597:
at C6 distinguishes the successive-generation fluoroquinolones from the first-generation of quinolones. The addition of the C6 fluorine atom has since been demonstrated not to be required for the
4449:
Suto MJ, Domagala JM, Roland GE, Mailloux GB, Cohen MA (December 1992). "Fluoroquinolones: relationships between structural variations, mammalian cell cytotoxicity, and antimicrobial activity".
4806:
Wentland MP: In memoriam: George Y. Lesher, PhD, in Hooper DC, Wolfson JS (eds): Quinolone antimicrobial agents, ed 2., Washington DC, American
Society for Microbiology : XIII – XIV, 1993.
5097:
2076:
Sung L, Manji A, Beyene J, Dupuis LL, Alexander S, Phillips R, Lehrnbecher T (May 2012). "Fluoroquinolones in children with fever and neutropenia: a systematic review of prospective trials".
387:
but serious adverse effects associated with all members of the fluoroquinolone antibacterial class. Among these, tendon problems and exacerbation of the symptoms of the neurological disorder
811:
at C-6 distinguishes the successive-generation fluoroquinolones from the first-generation quinolones, although examples are known that omit the atom while retaining antibacterial activity.
1452:
drugs found within this class (quinolones) within the first-generation heading. As such, a wide variation exists within the literature dependent upon the methods employed by the authors.
446:, but in practice, this appears relatively uncommon in part because the most widely prescribed fluoroquinolones (ciprofloxacin and levofloxacin) only minimally prolong the QT interval.
2273:"FDA Drug Safety Communication: FDA advises restricting fluoroquinolone antibiotic use for certain uncomplicated infections; warns about disabling side effects that can occur together"
4659:
2929:
488:, and products containing calcium, iron, or zinc invariably result in marked reduction of oral absorption of fluoroquinolones. Other drugs that interact with fluoroquinolones include
4677:"Briefing Information for the November 5, 2015 Joint Meeting of the Antimicrobial Drugs Advisory Committee (AMDAC) and the Drug Safety and Risk Management Advisory Committee (DSaRM)"
1416:. Naphthyridone and quinolone classes of antibiotics prevent bacterial DNA replication by inhibition of DNA unwinding events, and can be both bacteriostatic and bacteriocidal. (See
4533:
Zhanel GG, Fontaine S, Adam H, Schurek K, Mayer M, Noreddin AM, et al. (2006). "A Review of New
Fluoroquinolones : Focus on their Use in Respiratory Tract Infections".
2154:
1763:
78:
3096:
Van
Bambeke F, Tulkens PM (2009). "Safety profile of the respiratory fluoroquinolone moxifloxacin: comparison with other fluoroquinolones and other antibacterial classes".
5167:
4733:
4709:
2291:"Safety Alerts for Human Medical Products – Fluoroquinolone Antibiotics: FDA Requires Labeling Changes Due to Low Blood Sugar Levels and Mental Health Side Effects"
3503:
4703:"FDA Briefing Document Joint Meeting of the Antimicrobial Drugs Advisory Committee and the Drug Safety and Risk Management Advisory Committee, November 5, 2015"
2320:"Impact of the US Food and Drug Administration warning regarding increased risk of aortic aneurysms or aortic dissections on fluoroquinolone prescribing trends"
1934:
683:
pumps can act to decrease intracellular quinolone concentration. In gram-negative bacteria, plasmid-mediated resistance genes produce proteins that can bind to
450:
5139:
4680:
4285:"Cytotoxicity of quinolones toward eukaryotic cells. Identification of topoisomerase II as the primary cellular target for the quinolone CP-115,953 in yeast"
468:
The mechanisms of the toxicity of fluoroquinolones have been attributed to their interactions with different receptor complexes, such as blockade of the GABA
1375:
have been synthesized, but only a handful have found their way into clinical practice. The first generation also included other quinolone drugs, such as
673:
4727:"Transcript: Joint Meeting of the Antimicrobial Drugs Advisory Committee and the Drug Safety and Risk Management Advisory Committee, November 5, 2015"
268:
infections are licensed indications in the UK due to ongoing safety concerns. In a study comparing the safety and efficacy of levofloxacin to that of
3249:
676:. In addition, they are commonly prescribed for medical conditions, such as acute respiratory illness, that are usually caused by viral infections.
4751:
4414:
Castora FJ, Vissering FF, Simpson MV (September 1983). "The effect of bacterial DNA gyrase inhibitors on DNA synthesis in mammalian mitochondria".
3813:"Infectious Diseases Society of America/American Thoracic Society consensus guidelines on the management of community-acquired pneumonia in adults"
5060:
868:
3001:
460:
and seizure. Susceptible groups of patients, such as children and the elderly, are at greater risk of adverse reactions during therapeutic use.
1796:"Isolation and molecular characterization of nalidixic acid-resistant extraintestinal pathogenic Escherichia coli from retail chicken products"
6063:
5160:
5032:
3293:
5117:
2939:
5274:
3926:"Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story"
3965:
Linder JA, Huang ES, Steinman MA, Gonzales R, Stafford RS (March 2005). "Fluoroquinolone prescribing in the United States: 1995 to 2002".
2290:
3283:
3454:
3546:
Bar-Oz B, Moretti ME, Boskovic R, O'Brien L, Koren G (April 2009). "The safety of quinolones--a meta-analysis of pregnancy outcomes".
4508:
3733:
3352:
Farinas ER, et al. (Public Health Service Food and Drug Administration Center for Drug Evaluation and Research) (1 March 2005).
784:. For many Gram-negative bacteria, DNA gyrase is the target, whereas topoisomerase IV is the target for many Gram-positive bacteria.
5219:
5121:
2716:"FDA warns about increased risk of ruptures or tears in the aorta blood vessel with fluoroquinolone antibiotics in certain patients"
3672:
3486:
3002:"Disabling and potentially permanent side effects lead to suspension or restrictions of quinolone and fluoroquinolone antibiotics"
5153:
3784:
Hong CY, Kim SH, Kim YK (22 July 1997). "Novel 5-amino-6-methylquinolone antibacterials: A new class of non-6-fluoroquinolones".
624:
4399:
Bergan T, Dalhoff A, Thorsteinsson SB (July 1985). "A review of the pharmacokinetics and tissue penetration of ciprofloxacin.".
374:
cephalosporins. Fluoroquinoline administration may be associated with the acquisition and outgrowth of a particularly virulent
543:
symptoms due to quinolones displacing benzodiazepines from their binding sites. Fluoroquinolones have varying specificity for
6107:
1624:
Fourth-generation fluoroquinolones act at DNA gyrase and topoisomerase IV. This dual action slows development of resistance.
1980:
Liu H, Mulholland SG (July 2005). "Appropriate antibiotic treatment of genitourinary infections in hospitalized patients".
5510:
4974:
623:
Because the use of broad-spectrum antibiotics encourages the spread of multidrug-resistant strains and the development of
367:
55:
The second generation fluoroquinolone, ciprofloxacin. The two ringed nitrogen containing system with a ketone is called a
3455:"Guidance for the use and reduction of misuse of benzodiazepines and other hypnotics and anxiolytics in general practice"
2414:"Fluoroquinolones and tendinopathy: a guide for athletes and sports clinicians and a systematic review of the literature"
2366:
Stephenson AL, Wu W, Cortes D, Rochon PA (September 2013). "Tendon Injury and Fluoroquinolone Use: A Systematic Review".
2059:
5999:
4858:
3309:
Iannini PB (June 2007). "The safety profile of moxifloxacin and other fluoroquinolones in special patient populations".
2934:
661:, commonly exhibit resistance. Widespread veterinary usage of quinolones, in particular in Europe, has been implicated.
287:
4936:
6080:
3499:
4054:
Robicsek A, Jacoby GA, Hooper DC (October 2006). "The worldwide emergence of plasmid-mediated quinolone resistance".
4011:"Antibiotic resistance among gram-negative bacilli in US intensive care units: implications for fluoroquinolone use"
3353:
915:
750:
4859:"New Classification and Update on the Quinolone Antibiotics – May 1, 2000 – American Academy of Family Physicians"
2966:
De Sarro A, De Sarro G (March 2001). "Adverse reactions to fluoroquinolones. an overview on mechanistic aspects".
2805:"Antibiotics and hospital-acquired Clostridium difficile infection: update of systematic review and meta-analysis"
2786:
719:
by preventing bacterial DNA from unwinding and duplicating. Specifically, they inhibit the ligase activity of the
540:
536:
145:
240:, fluoroquinolones are the "drugs of choice" due to their ability to enter bone tissue without chelating it, as
5525:
1359:
641:
114:
472:
receptor complex within the central nervous system, leading to excitotoxic type effects and oxidative stress.
5129:
4782:
4580:
6068:
5576:
4756:
2846:"Risk factors for development of Clostridium difficile infection due to BI/NAP1/027 strain: a meta-analysis"
5520:
5111:
4634:
4091:"NorM, a putative multidrug efflux protein, of Vibrio parahaemolyticus and its homolog in Escherichia coli"
3021:"Macrolides vs. quinolones for community-acquired pneumonia: meta-analysis of randomized controlled trials"
1757:
5952:
5424:
5391:
5363:
5321:
5284:
5269:
5180:
907:
895:
774:
564:
356:
316:
278:
247:
Fluoroquinolones are featured prominently in guidelines for the treatment of hospital-acquired pneumonia.
298:
While typical drug side effects reactions are mild to moderate, sometimes serious adverse effects occur.
290:, or when alternative treatment options require parenteral administration and oral therapy is preferred.
5347:
5343:
5227:
5145:
5102:
3668:
2148:
1387:, which were introduced in the 1970s. They proved to be only marginal improvements over nalidixic acid.
780:
731:
720:
680:
648:
618:
223:
where the person may need to be hospitalised, fluoroquinolones are recommended as first-line therapy.
4340:
560:
1331:. The other parameters an average of the values available in the literature irrespective of dosage.
749:
could be bactericidal. Bacterial cytotoxicity could arise from incomplete repair of closely spaced
5696:
2250:
858:
848:
830:
443:
438:
227:
5470:
3811:
Mandell LA, Wunderink RG, Anzueto A, Bartlett JG, Campbell GD, Dean NC, et al. (March 2007).
1950:
5947:
5419:
4558:
3714:
3650:
3607:
3435:
3334:
3121:
2741:
Deshpande A, Pasupuleti V, Thota P, Pant C, Rolston DD, Sferra TJ, et al. (September 2013).
2599:
2521:
2391:
2101:
2041:
937:
880:
5203:
5028:
5022:
4928:
4839:
4550:
4485:
4466:
4431:
4366:
4306:
4265:
4221:
4172:
4120:
4071:
4032:
3982:
3947:
3891:
3842:
3756:
3706:
3642:
3599:
3563:
3528:
3427:
3387:
3326:
3289:
3257:
3230:
3189:
3162:
3113:
3078:
3042:
2983:
2911:
2867:
2826:
2764:
2697:
2648:
2591:
2556:
2513:
2478:
2443:
2383:
2341:
2232:
2191:
2136:
2093:
2033:
1997:
1962:
1954:
1915:
1866:
1825:
1794:
Johnson JR, Murray AC, Gajewski A, Sullivan M, Snippes P, Kuskowski MA, Smith KE (July 2003).
1372:
789:
735:
614:
389:
307:
152:
672:, and acute upper respiratory tract infection, according to a study supported in part by the
5692:
5515:
5399:
5371:
4829:
4542:
4500:
4458:
4423:
4356:
4348:
4296:
4255:
4211:
4203:
4162:
4154:
4110:
4102:
4063:
4022:
3974:
3937:
3881:
3873:
3832:
3824:
3793:
3748:
3698:
3634:
3591:
3555:
3461:
3419:
3318:
3220:
3152:
3105:
3070:
3032:
2975:
2901:
2857:
2816:
2754:
2687:
2679:
2638:
2630:
2583:
2548:
2505:
2470:
2433:
2425:
2375:
2331:
2222:
2181:
2128:
2085:
2025:
1989:
1946:
1905:
1897:
1856:
1815:
1807:
1691:
927:
711:
Structure of bacterial DNA gyrase complexed with DNA and two ciprofloxacin molecules (green)
696:
665:
657:
576:
509:
4597:
Wentland MP (1993). "In memoriam: George Y. Lesher, PhD". In Hooper DC, Wolfson JS (eds.).
4329:"Oxidation of the guanine nucleotide pool underlies cell death by bactericidal antibiotics"
2668:"Association of Fluoroquinolone Use With Short-term Risk of Development of Aortic Aneurysm"
5588:
5414:
5133:
5092:
3507:
837:
762:
716:
544:
453:
it was discovered that fluoroquinolones could increase the risk for heart valve diseases.
436:
by blocking voltage-gated potassium channels. Prolongation of the QT interval can lead to
352:
330:
312:
265:
4344:
3689:
Scherer K, Bircher AJ (January 2005). "Hypersensitivity reactions to fluoroquinolones".
3180:
Heidelbaugh JJ, Holmstrom H (April 2013). "The perils of prescribing fluoroquinolones".
699:
can decrease their binding affinity to quinolones, decreasing the drugs' effectiveness.
6074:
5961:
5831:
5631:
5626:
5616:
5480:
5475:
5439:
5297:
4834:
4817:
4778:
4576:
4361:
4328:
4216:
4191:
4167:
4142:
3886:
3861:
3837:
3812:
3638:
2743:"Community-associated Clostridium difficile infection and antibiotics: a meta-analysis"
2692:
2667:
2643:
2618:
2438:
2413:
1910:
1885:
1506:
1502:
1498:
1376:
1355:
1350:, it is considered the predecessor of all subsequently developed quinolone antibiotics.
457:
216:
4601:. Vol. XIII–XIV (2nd ed.). Washington DC: American Society for Microbiology.
4301:
4284:
4115:
4090:
4089:
Morita Y, Kodama K, Shiota S, Mine T, Kataoka A, Mizushima T, Tsuchiya T (July 1998).
4067:
4009:
Neuhauser MM, Weinstein RA, Rydman R, Danziger LH, Karam G, Quinn JP (February 2003).
3797:
2844:
Vardakas KZ, Konstantelias AA, Loizidis G, Rafailidis PI, Falagas ME (November 2012).
2319:
2060:"Adverse Event Review: Levaquin® (levofloxacin): Pediatric Advisory Committee Meeting"
1820:
1795:
194:
6101:
5929:
5879:
5869:
5827:
5817:
5807:
5739:
5663:
5621:
5541:
5465:
5434:
5353:
5339:
5327:
5317:
5311:
5307:
5302:
5292:
5247:
5087:
4546:
4427:
3378:
Saint F, Salomon L, Cicco A, de la Taille A, Chopin D, Abbou CC (December 2001). "".
3109:
3037:
3020:
2715:
2272:
1901:
1722:
1669:
1664:
Two structurally related fourth-generation drugs, but formally not 4-quinolones, are
1648:
1628:
1586:
1520:
1482:
1460:
1380:
1347:
949:
801:
766:
598:
583:
406:
394:
241:
231:
208:
183:
179:
175:
148:
83:
4562:
3718:
3654:
3611:
3439:
3338:
3125:
2603:
2525:
2395:
2132:
2105:
2045:
1811:
1493:
Structurally related first-generation drugs, but formally not 4-quinolones, include
1362:(UTIs) in humans. Nalidixic acid was discovered by George Lesher and coworkers in a
320:
syndrome, atherosclerosis, peripheral vascular disease, and a history of aneurysms.
5884:
5874:
5859:
5849:
5822:
5802:
5797:
5792:
5787:
5782:
5777:
5759:
5754:
5749:
5744:
5734:
5729:
5688:
5683:
5485:
5376:
5257:
5188:
5184:
1734:
1728:
1710:
1698:
1665:
1658:
1653:
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1638:
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1613:
1606:
1601:
1596:
1591:
1581:
1574:
1535:
1530:
1464:
1456:
1358:
is considered the first quinolone drug. It was introduced in 1962 for treatment of
1261:
1195:
1133:
1093:
669:
525:
517:
501:
269:
198:
101:
17:
3423:
3354:"Consult: One-Year Post Pediatric Exclusivity Postmarketing Adverse Events Review"
1935:"Should Physicians Consider the Environmental Effects of Prescribing Antibiotics?"
1561:
A structurally related second-generation drug, but formally not a 4-quinolone, is
1516:
The second-generation class is sometimes subdivided into "Class 1" and "Class 2".
3978:
3595:
3559:
3410:
Fish DN (October 2001). "Fluoroquinolone adverse effects and drug interactions".
2552:
2089:
1993:
1612:
A structurally related third-generation drug, but formally not a 4-quinolone, is
120:
6045:
6037:
6017:
5970:
5904:
5864:
5812:
5701:
5551:
5490:
5444:
5404:
5381:
5252:
5232:
5176:
3282:
Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (2006).
2574:
Mehlhorn AJ, Brown DA (November 2007). "Safety concerns with fluoroquinolones".
1716:
1573:
Unlike the first and second generations, the third generation is active against
1540:
1436:
1413:
1367:
1011:
568:
529:
433:
422:
418:
273:
261:
220:
156:
5112:
Healthcare-associated Infections (HAIs)- Quinolones and the Clinical Laboratory
4966:
4504:
3752:
2862:
2845:
2683:
2474:
2119:
Rosanova MT, Lede R, Capurro H, Petrungaro V, Copertari P (December 2010). "".
1884:
Heeb S, Fletcher MP, Chhabra SR, Diggle SP, Williams P, Cámara M (March 2011).
6007:
5933:
5920:
5909:
5854:
5711:
5706:
5678:
5611:
5581:
5429:
5242:
5197:
4996:
3702:
3019:
Skalsky K, Yahav D, Lador A, Eliakim-Raz N, Leibovici L, Paul M (April 2013).
2429:
2379:
2336:
2186:
2169:
2029:
1704:
1679:
1555:
1550:
1525:
1476:
1440:
1409:
1363:
692:
684:
651:
to quinolones can evolve rapidly, even during a course of treatment. Numerous
497:
493:
489:
426:
414:
405:
lead to an emergency department visit more frequently than those treated with
236:
41:
5118:
Information for Healthcare Professionals: Fluoroquinolone Antimicrobial Drugs
4870:
3322:
3261:
2979:
2634:
2509:
1958:
6027:
6022:
6012:
5994:
5668:
5636:
5606:
5556:
5409:
5332:
4916:
4352:
1545:
1494:
1487:
1384:
1342:
707:
631:
587:
513:
410:
160:
95:
56:
5142:"Antibacterial Agents; Structure Activity Relationships," André Bryskier MD
4932:
4843:
4554:
4370:
4269:
4225:
4176:
4158:
4075:
4036:
4027:
4010:
3986:
3951:
3895:
3877:
3846:
3710:
3646:
3603:
3567:
3532:
3431:
3391:
3330:
3234:
3225:
3208:
3193:
3166:
3117:
3082:
3046:
2987:
2915:
2871:
2830:
2768:
2701:
2595:
2560:
2517:
2482:
2447:
2387:
2345:
2236:
2227:
2210:
2195:
2140:
2097:
2037:
2001:
1966:
1919:
1870:
1829:
1443:
moiety, and the remaining substitution sites (R groups) are hydrogen atoms.
204:
50:
4470:
4435:
4310:
4124:
4106:
2652:
1427:
to the all-carbon containing ring, typically at the C-6 or C-8 positions.
1412:
during an attempt at synthesis of the chloroquinoline antimalarial agent,
133:
5673:
5460:
5237:
2821:
2804:
2759:
2742:
1861:
1844:
1562:
1449:
1421:
805:
769:
724:
688:
652:
591:
556:
521:
505:
485:
171:
4462:
3625:
Leibovitz E (February 2006). "The use of fluoroquinolones in children".
820:
Pharmacokinetics of newer fluoroquinolones following a single oral dose
715:
Quinolones are chemotherapeutic bactericidal drugs. They interfere with
630:
first-line agent for community-acquired pneumonia, instead recommending
5546:
3074:
257:
4207:
3141:"Emergency department visits for antibiotic-associated adverse events"
2587:
1430:
586:, or active structure, of the fluoroquinolone class is based upon the
5106:
4327:
Foti JJ, Devadoss B, Winkler JA, Collins JJ, Walker GC (April 2012).
3911:
International Symposium on Antimicrobial Agents and Resistance. Drugs
1455:
The first generation is rarely used. Frequently prescribed drugs are
572:
481:
215:
antibiotic regimens have failed. However, for serious acute cases of
3909:
Jacobs M (2005). "Worldwide overview of antimicrobial Resistance.".
3548:
European Journal of Obstetrics, Gynecology, and Reproductive Biology
2883:
2881:
159:. They are used in human and veterinary medicine to treat bacterial
4416:
Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression
4260:
4243:
3942:
3925:
3828:
3157:
3140:
2906:
2889:
571:, pre-existing CNS lesions, or CNS inflammation, or who have had a
163:, as well as in animal husbandry, specifically poultry production.
5126:
1429:
1341:
706:
203:
193:
3862:"Antimicrobial drug prescribing for pneumonia in ambulatory care"
4486:"Activities of Quinolones Against Obligately Anaerobic Bacteria"
3860:
MacDougall C, Guglielmo BJ, Maselli J, Gonzales R (March 2005).
3734:"Activities of Quinolones Against Obligately Anaerobic Bacteria"
2496:
Babar SM (October 2013). "SIADH associated with ciprofloxacin".
1424:
825:
808:
727:
594:
174:
atom in their chemical structure and are effective against both
5149:
4384:
Bergan T (1988). "Pharmacokinetics of fluorinated quinolones".
3139:
Shehab N, Patel PR, Srinivasan A, Budnitz DS (September 2008).
869:
5984:
4818:"Quinolone generations: natural history or natural selection?"
746:
456:
Events that may occur in acute overdose are rare, and include
2170:"Do fluoroquinolones commonly cause arthropathy in children?"
4997:"Consolidated list of products – Pharmaceuticals 12th issue"
1694:, and several agents have veterinary-specific applications.
2666:
Newton ER, Akerman AW, Strassle PD, Kibbe MR (March 2021).
5136:"Family Practice Notebook" entry page for Fluoroquinolones
3924:
Nelson JM, Chiller TM, Powers JH, Angulo FJ (April 2007).
2018:
American Journal of Respiratory and Critical Care Medicine
3487:"Fluoroquinolones Antibiotic Alert – especially with EDS"
687:, protecting it from the action of quinolones. Finally,
679:
Three mechanisms of resistance are known. Some types of
634:
or doxycycline as first-line agents. The Drug-Resistant
3519:
Nardiello S, Pizzella T, Ariviello R (March 2002). "".
5024:
Clinical Ophthalmology: Contemporary Perspectives, 9/e
4635:"FDA updates warnings for fluoroquinolone antibiotics"
2787:"Data Mining Analysis of Multiple Antibiotics in AERS"
730:
attached to the central ring system, typically at the
1764:
United States Department of Health and Human Services
186:, one of the most widely used antibiotics worldwide.
2318:
Rizk JG, Slejko JF, Heil EL, Seo D, Qato DM (2024).
1759:
FDA updates warnings for fluoroquinolone antibiotics
27:
Class of antibacterial drugs, subgroup of quinolones
6036:
5993:
5983:
5960:
5946:
5918:
5897:
5840:
5768:
5720:
5654:
5645:
5597:
5569:
5534:
5503:
5453:
5390:
5362:
5283:
5268:
5218:
5196:
4143:"Emerging mechanisms of fluoroquinolone resistance"
2407:
2405:
127:
113:
108:
94:
89:
77:
69:
64:
34:
4971:Seminars in Respiratory and Critical Care Medicine
3405:
3403:
3401:
2313:
2311:
2251:"FDA orders 'black box' label on some antibiotics"
2211:"The use of systemic and topical fluoroquinolones"
4910:
4908:
4403:. Hong Kong: Sieber and McIntyre. pp. 23–36.
2890:"Antimicrobial safety: focus on fluoroquinolones"
2361:
2359:
2357:
2355:
2153:: CS1 maint: DOI inactive as of September 2024 (
2065:. Food and Drug Administration. 18 November 2008.
741:active against eukaryotic type II topoisomerase.
4906:
4904:
4902:
4900:
4898:
4896:
4894:
4892:
4890:
4888:
3288:. New York: McGraw-Hill, Medical Pub. Division.
256:children are severely restricted. Only inhalant
4616:. San Diego: Academic Press Inc. pp. 1–22.
2961:
2959:
2957:
1933:Balch J, Schoen JH, Patel PK (1 October 2017).
874:Tooltip Area under the curve (pharmacokinetics)
761:Fluoroquinolones can enter in cells easily via
4679:. Food and Drug Administration. Archived from
4192:"Mechanism of quinolone action and resistance"
4190:Aldred KJ, Kerns RJ, Osheroff N (March 2014).
1886:"Quinolones: from antibiotics to autoinducers"
896:
753:in the DNA resulting in double-strand breaks.
555:Quinolones are not recommended in people with
413:, but less frequently than those treated with
5161:
4283:Elsea SH, Osheroff N, Nitiss JL (July 1992).
1951:10.1001/journalofethics.2017.19.10.peer1-1710
535:Administration of quinolone antibiotics to a
484:, such as aluminium- or magnesium-containing
451:Journal of the American College of Cardiology
8:
4629:
4627:
4625:
4623:
4493:Anti-Infective Agents in Medicinal Chemistry
3786:Bioorganic & Medicinal Chemistry Letters
3779:
3777:
3741:Anti-Infective Agents in Medicinal Chemistry
2850:International Journal of Infectious Diseases
1328:
166:Nearly all quinolone antibiotics in use are
4960:
4958:
4956:
4954:
4752:"FDA Panel Seeks Tougher Antibiotic Labels"
4322:
4320:
4244:"The quinolones: past, present, and future"
609:Antibiotic misuse and bacterial resistances
5990:
5957:
5651:
5594:
5280:
5215:
5168:
5154:
5146:
4136:
4134:
3250:"Antibiotics Tied to Heart Valve Problems"
2785:Levine JG, Szarfman A (15 December 2006).
938:
881:
674:Agency for Healthcare Research and Quality
49:
4857:Lilley SH, Malone R, King DE (May 2000).
4833:
4822:The Journal of Antimicrobial Chemotherapy
4653:"Fluoroquinolone Safety Labeling Changes"
4360:
4300:
4259:
4237:
4235:
4215:
4166:
4114:
4026:
3941:
3885:
3836:
3224:
3213:The Journal of Antimicrobial Chemotherapy
3156:
3036:
2905:
2861:
2820:
2809:The Journal of Antimicrobial Chemotherapy
2780:
2778:
2758:
2747:The Journal of Antimicrobial Chemotherapy
2691:
2642:
2437:
2335:
2226:
2185:
1909:
1860:
1849:The Journal of Antimicrobial Chemotherapy
1819:
1713:– 2nd gen, metabolizes into ciprofloxacin
5096:) is being considered for deletion. See
4965:Ambrose PG, Owens Jr RC (1 March 2000).
4783:"NegGram® Caplets (nalidixic acid, USP)"
4484:Schaumann R, Rodloff AC (January 2007).
3732:Schaumann R, Rodloff AC (January 2007).
3584:The Pediatric Infectious Disease Journal
2539:Rouveix B (November–December 2006). "".
2078:The Pediatric Infectious Disease Journal
1417:
928:
818:
5057:"Drug Company Taking Tequin Off Market"
4915:Oliphant CM, Green GM (February 2002).
4581:"NegGram Caplets (nalidixic acid, USP)"
3673:"Highlights of Prescribing Information"
2209:Bradley JS, Jackson MA (October 2011).
2168:Forsythe CT, Ernst ME (November 2007).
1771:
1346:Nalidixic acid. Although technically a
1321:
838:
230:being at increased risk for developing
5769:
5655:
4939:from the original on 29 September 2007
2146:
1843:Andersson MI, MacGowan AP (May 2003).
1707:– 2nd/3rd gen, related to temafloxacin
1439:group, the R substituent in blue is a
31:
5721:
5598:
4095:Antimicrobial Agents and Chemotherapy
1800:Antimicrobial Agents and Chemotherapy
432:Fluoroquinolones prolong the heart's
100:
7:
4917:"Quinolones: a comprehensive review"
4614:The quinolones: history and overview
3311:Current Medical Research and Opinion
3209:"Cardiotoxicity of fluoroquinolones"
2792:. U.S. Food and Drug Administration.
1737:– 2nd/3rd gen, related to difloxacin
1690:Quinolones have been widely used in
333:. The cause is not well understood.
5841:
4967:"Clinical Usefulness of Quinolones"
4658:. FDA. 4 April 2017. Archived from
4388:. Academic Press. pp. 119–154.
4289:The Journal of Biological Chemistry
3285:Goldfrank's toxicologic emergencies
3207:Rubinstein E, Camm J (April 2002).
3025:Clinical Microbiology and Infection
2803:Slimings C, Riley TV (April 2014).
1701:– 2nd gen, related to ciprofloxacin
1354:Although not formally a quinolone,
5059:. Associated Press. Archived from
4835:10.1093/oxfordjournals.jac.a020889
4535:Treatments in Respiratory Medicine
3691:Current Allergy and Asthma Reports
3639:10.1097/01.mop.0000192520.48411.fa
2888:Owens RC, Ambrose PG (July 2005).
1731:– 3rd gen, related to sparfloxacin
1725:– 3rd gen, related to levofloxacin
1719:– 3rd gen, related to levofloxacin
734:. Most of them are named with the
25:
5122:U.S. Food and Drug Administration
5100:to help reach a consensus. ›
5027:. Elsevier India. pp. 112–.
4977:from the original on 23 June 2011
4514:from the original on 16 June 2010
2619:"Quinolones may induce hepatitis"
2617:Jones SE, Smith RH (March 1997).
2541:Médecine et Maladies Infectieuses
590:ring system. The addition of the
539:individual can precipitate acute
5140:Structure Activity Relationships
4547:10.2165/00151829-200605060-00009
3967:The American Journal of Medicine
3110:10.2165/00002018-200932050-00001
3038:10.1111/j.1469-0691.2012.03838.x
2121:Archivos Argentinos de Pediatria
1982:The American Journal of Medicine
1902:10.1111/j.1574-6976.2010.00247.x
1751: This article incorporates
1746:
480:Products containing multivalent
4586:. Food and Drug Administration.
4401:Ciprofloxacin A new 4–quinolone
4339:(6079). New York, N.Y.: 315–9.
4056:The Lancet. Infectious Diseases
3678:. Food and Drug Administration.
3248:Bakalar N (17 September 2019).
2133:10.1590/S0325-00752010000600008
1845:"Development of the quinolones"
1812:10.1128/AAC.47.7.2161-2168.2003
1254:
1250:
1086:
1082:
1077:
1073:
1068:
1061:
1054:
1050:
1033:
1021:
4869:(9): 2741–2748. Archived from
4599:Quinolone antimicrobial agents
4451:Journal of Medicinal Chemistry
4141:Hooper DC (March–April 2001).
3502:levaquinadversesideeffect.com
3359:. Food and Drug Administration
3182:The Journal of Family Practice
2135:(inactive 18 September 2024).
901:Tooltip Volume of distribution
1:
5511:Trimethoprim/sulfamethoxazole
4750:Burton TM (6 November 2015).
4612:Norris S, Mandell GL (1988).
4302:10.1016/S0021-9258(18)42185-0
4068:10.1016/S1473-3099(06)70599-0
3798:10.1016/S0960-894X(97)00324-7
3627:Current Opinion in Pediatrics
3424:10.1592/phco.21.16.253S.33993
2576:The Annals of Pharmacotherapy
2498:The Annals of Pharmacotherapy
1672:(removed from clinical use).
765:, so are often used to treat
4428:10.1016/0167-4781(83)90090-8
4248:Clinical Infectious Diseases
4147:Emerging Infectious Diseases
3979:10.1016/j.amjmed.2004.09.015
3930:Clinical Infectious Diseases
3866:Emerging Infectious Diseases
3817:Clinical Infectious Diseases
3596:10.1097/INF.0b013e3180cbd382
3560:10.1016/j.ejogrb.2008.12.007
3145:Clinical Infectious Diseases
2935:Food and Drug Administration
2894:Clinical Infectious Diseases
2553:10.1016/j.medmal.2006.05.012
2418:Journal of Athletic Training
2090:10.1097/INF.0b013e318245ab48
1994:10.1016/j.amjmed.2005.05.009
306:In 2008, the U.S. FDA added
288:multidrug-resistant bacteria
144:constitute a large group of
5516:Ormetoprim/sulfadimethoxine
3453:Ford C, Law F (July 2014).
2968:Current Medicinal Chemistry
6124:
4505:10.2174/187152107779314179
3753:10.2174/187152107779314179
2863:10.1016/j.ijid.2012.07.010
2684:10.1001/jamasurg.2020.6165
2475:10.1016/j.phrs.2004.08.003
1323:= Dosage applies only to C
1322:
943:Tooltip Hepatic impairment
889:Tooltip Terminal half-life
732:6-position or C-8 position
612:
6058:
5526:Pyrimethamine/sulfadoxine
4921:American Family Physician
4863:American Family Physician
4242:Andriole VT (July 2005).
3703:10.1007/s11882-005-0049-1
3006:European Medicines Agency
2430:10.4085/1062-6050-49.2.09
2380:10.1007/s40264-013-0089-8
2337:10.1136/bmjoq-2024-002925
2187:10.1017/s1481803500015517
2030:10.1164/rccm.200405-644ST
1890:FEMS Microbiology Reviews
921:
914:
906:
894:
879:
867:
857:
847:
836:
829:
824:
541:benzodiazepine withdrawal
182:bacteria. One example is
155:related to the substance
132:
48:
39:
5098:templates for discussion
5055:Schmid RE (1 May 2006).
3521:Le Infezioni in Medicina
3323:10.1185/030079907X188099
2980:10.2174/0929867013373435
2635:10.1136/bmj.314.7084.869
2510:10.1177/1060028013502457
2463:Pharmacological Research
2412:Lewis T, Cook J (2014).
1360:urinary tract infections
933:Tooltip Renal impairment
642:Streptococcus pneumoniae
636:Streptococcus pneumoniae
601:activity of this class (
537:benzodiazepine-dependent
4828:(Supplement 3): 17–24.
4779:Sanofi-Aventis U.S. LLC
4757:The Wall Street Journal
4577:Sanofi-Aventis U.S. LLC
4353:10.1126/science.1219192
3999:K08 HS14563 and HS11313
3460:. SMMGP. Archived from
3063:Mayo Clinic Proceedings
843:Tooltip Bioavailability
751:8-oxo-2'-deoxyguanosine
153:bicyclic core structure
5425:Sulfamethoxypyridazine
5002:. United Nations. 2005
4159:10.3201/eid0702.010239
4028:10.1001/jama.289.7.885
3878:10.3201/eid1103.040819
3418:(10 Pt 2): 253S–272S.
2900:(Suppl 2): S144–S157.
2790:(Microsoft PowerPoint)
2228:10.1542/peds.2011-1496
1753:public domain material
1444:
1351:
775:Legionella pneumophila
721:type II topoisomerases
712:
565:Ehlers-Danlos Syndrome
397:in the United States.
357:Ehlers-Danlos syndrome
317:mental health problems
279:central nervous system
211:
201:
6108:Quinolone antibiotics
5898:Newer non-fluorinated
5535:Other DHPS inhibitors
5521:Pyrimethamine/dapsone
5348:Succinylsulfathiazole
5344:Phthalylsulfathiazole
5228:2,4-Diaminopyrimidine
4732:. FDA. Archived from
4708:. FDA. Archived from
4107:10.1128/AAC.42.7.1778
3669:Janssen Pharmaceutica
1988:(Suppl 7A): 14S–20S.
1939:AMA Journal of Ethics
1433:
1366:during an attempt at
1345:
781:Mycoplasma pneumoniae
710:
626:Clostridium difficile
619:Antibiotic resistance
464:Mechanism of toxicity
442:, a life-threatening
369:Clostridium difficile
207:
197:
142:Quinolone antibiotics
5322:Acetyl sulfisoxazole
5181:inhibit nucleic acid
5132:17 June 2006 at the
5103:Quinolone antibiotic
4816:Ball P (July 2000).
4715:on 17 November 2015.
3823:(Suppl 2): S27–S72.
3506:17 June 2021 at the
3226:10.1093/jac/49.4.593
2330:(e002925): e002925.
1779:Andriole VT (1989).
1448:grouping of the non-
395:"black box" warnings
5697:Alalevonadifloxacin
5364:Intermediate-acting
5063:on 25 November 2007
4739:on 8 February 2016.
4463:10.1021/jm00103a013
4345:2012Sci...336..315F
4295:(19): 13150–13153.
3913:. pp. 542–546.
3380:Progres en Urologie
1418:Mechanism of Action
821:
703:Mechanism of action
579:to the drug class.
439:torsades de pointes
393:are the subject of
228:sickle-cell disease
226:Due to people with
73:Bacterial infection
18:2- and 4-Quinolones
6085:Never to phase III
5586:thereby inhibiting
5574:(inhibit bacterial
5420:Sulfametoxydiazine
5208:thereby inhibiting
5201:(inhibit bacterial
4781:(September 2008).
4683:on 20 October 2015
4579:(September 2008).
3671:(September 2008).
3254:The New York Times
3075:10.4065/81.12.1553
2942:on 30 October 2017
2822:10.1093/jac/dkt477
2760:10.1093/jac/dkt129
2722:. 20 December 2018
2547:(11–12): 697–705.
2253:. CNN. 8 July 2008
2221:(4): e1034–e1045.
1862:10.1093/jac/dkg212
1855:(Suppl S1): 1–11.
1445:
1352:
819:
713:
308:black box warnings
212:
202:
170:, which contain a
6095:
6094:
6054:
6053:
5979:
5978:
5942:
5941:
5893:
5892:
5565:
5564:
5499:
5498:
5204:purine metabolism
5034:978-81-312-1680-4
4457:(25): 4745–4750.
4254:(S2): S113–S119.
4208:10.1021/bi5000564
4202:(10): 1565–1574.
3792:(14): 1875–1878.
3489:. 29 August 2013.
3295:978-0-07-143763-9
3069:(12): 1553–1566.
2856:(11): e768–e773.
2588:10.1345/aph.1K347
2582:(11): 1859–1866.
2504:(10): 1359–1363.
1783:. Academic Press.
1620:Fourth generation
1616:(Ozex, Tosacin).
1512:Second generation
1335:
1334:
790:mitochondrial DNA
615:Antibiotic misuse
561:Marfan's syndrome
551:Contraindications
449:In 2019 study by
390:myasthenia gravis
346:Aortic dissection
244:are known to do.
139:
138:
65:Class identifiers
16:(Redirected from
6115:
5991:
5958:
5693:Levonadifloxacin
5652:
5647:Fluoroquinolones
5595:
5400:Sulfadimethoxine
5372:Sulfamethoxazole
5293:Sulfaisodimidine
5281:
5216:
5170:
5163:
5156:
5147:
5127:Fluoroquinolones
5073:
5072:
5070:
5068:
5052:
5046:
5045:
5043:
5041:
5018:
5012:
5011:
5009:
5007:
5001:
4993:
4987:
4986:
4984:
4982:
4962:
4949:
4948:
4946:
4944:
4912:
4883:
4882:
4880:
4878:
4854:
4848:
4847:
4837:
4813:
4807:
4804:
4798:
4797:
4795:
4793:
4787:
4775:
4769:
4768:
4766:
4764:
4747:
4741:
4740:
4738:
4731:
4723:
4717:
4716:
4714:
4707:
4699:
4693:
4692:
4690:
4688:
4673:
4667:
4666:
4664:
4657:
4649:
4643:
4642:
4631:
4618:
4617:
4609:
4603:
4602:
4594:
4588:
4587:
4585:
4573:
4567:
4566:
4530:
4524:
4523:
4521:
4519:
4513:
4490:
4481:
4475:
4474:
4446:
4440:
4439:
4411:
4405:
4404:
4396:
4390:
4389:
4381:
4375:
4374:
4364:
4324:
4315:
4314:
4304:
4280:
4274:
4273:
4263:
4239:
4230:
4229:
4219:
4187:
4181:
4180:
4170:
4138:
4129:
4128:
4118:
4101:(7): 1778–1782.
4086:
4080:
4079:
4051:
4045:
4044:
4030:
4006:
4000:
3997:
3991:
3990:
3962:
3956:
3955:
3945:
3921:
3915:
3914:
3906:
3900:
3899:
3889:
3857:
3851:
3850:
3840:
3808:
3802:
3801:
3781:
3772:
3771:
3769:
3767:
3761:
3755:. Archived from
3738:
3729:
3723:
3722:
3686:
3680:
3679:
3677:
3665:
3659:
3658:
3622:
3616:
3615:
3578:
3572:
3571:
3543:
3537:
3536:
3516:
3510:
3497:
3491:
3490:
3483:
3477:
3476:
3474:
3472:
3466:
3459:
3450:
3444:
3443:
3407:
3396:
3395:
3386:(6): 1331–1334.
3375:
3369:
3368:
3366:
3364:
3358:
3349:
3343:
3342:
3317:(6): 1403–1413.
3306:
3300:
3299:
3279:
3273:
3272:
3270:
3268:
3245:
3239:
3238:
3228:
3204:
3198:
3197:
3177:
3171:
3170:
3160:
3136:
3130:
3129:
3093:
3087:
3086:
3057:
3051:
3050:
3040:
3016:
3010:
3009:
3008:. 11 March 2019.
2998:
2992:
2991:
2963:
2952:
2951:
2949:
2947:
2938:. Archived from
2926:
2920:
2919:
2909:
2885:
2876:
2875:
2865:
2841:
2835:
2834:
2824:
2800:
2794:
2793:
2791:
2782:
2773:
2772:
2762:
2753:(9): 1951–1961.
2738:
2732:
2731:
2729:
2727:
2712:
2706:
2705:
2695:
2663:
2657:
2656:
2646:
2614:
2608:
2607:
2571:
2565:
2564:
2536:
2530:
2529:
2493:
2487:
2486:
2458:
2452:
2451:
2441:
2409:
2400:
2399:
2363:
2350:
2349:
2339:
2324:BMJ Open Quality
2315:
2306:
2305:
2303:
2301:
2287:
2281:
2280:
2269:
2263:
2262:
2260:
2258:
2247:
2241:
2240:
2230:
2206:
2200:
2199:
2189:
2165:
2159:
2158:
2152:
2144:
2116:
2110:
2109:
2073:
2067:
2066:
2064:
2056:
2050:
2049:
2012:
2006:
2005:
1977:
1971:
1970:
1930:
1924:
1923:
1913:
1881:
1875:
1874:
1864:
1840:
1834:
1833:
1823:
1806:(7): 2161–2168.
1791:
1785:
1784:
1776:
1767:
1750:
1749:
1692:animal husbandry
1675:In development:
1569:Third generation
1479:(veterinary use)
1471:First generation
1330:
1256:
1252:
1088:
1084:
1079:
1075:
1070:
1063:
1056:
1052:
1035:
1023:
944:
940:
934:
930:
922:Dose adjustment
902:
898:
890:
886:
875:
871:
844:
840:
822:
815:Pharmacokinetics
697:topoisomerase IV
691:at key sites in
666:acute bronchitis
658:Escherichia coli
577:hypersensitivity
510:antiviral agents
168:fluoroquinolones
123:
104:
53:
32:
21:
6123:
6122:
6118:
6117:
6116:
6114:
6113:
6112:
6098:
6097:
6096:
6091:
6090:
6075:Clinical trials
6050:
6032:
5998:
5975:
5951:
5938:
5914:
5889:
5836:
5764:
5716:
5641:
5589:DNA replication
5587:
5585:
5579:
5575:
5573:
5561:
5530:
5495:
5454:Other/ungrouped
5449:
5415:Sulfametomidine
5386:
5358:
5272:
5264:
5211:
5209:
5207:
5202:
5200:
5192:
5174:
5134:Wayback Machine
5101:
5082:
5077:
5076:
5066:
5064:
5054:
5053:
5049:
5039:
5037:
5035:
5020:
5019:
5015:
5005:
5003:
4999:
4995:
4994:
4990:
4980:
4978:
4964:
4963:
4952:
4942:
4940:
4914:
4913:
4886:
4876:
4874:
4856:
4855:
4851:
4815:
4814:
4810:
4805:
4801:
4791:
4789:
4785:
4777:
4776:
4772:
4762:
4760:
4749:
4748:
4744:
4736:
4729:
4725:
4724:
4720:
4712:
4705:
4701:
4700:
4696:
4686:
4684:
4675:
4674:
4670:
4662:
4655:
4651:
4650:
4646:
4641:. 26 July 2016.
4633:
4632:
4621:
4611:
4610:
4606:
4596:
4595:
4591:
4583:
4575:
4574:
4570:
4532:
4531:
4527:
4517:
4515:
4511:
4488:
4483:
4482:
4478:
4448:
4447:
4443:
4413:
4412:
4408:
4398:
4397:
4393:
4383:
4382:
4378:
4326:
4325:
4318:
4282:
4281:
4277:
4241:
4240:
4233:
4189:
4188:
4184:
4140:
4139:
4132:
4088:
4087:
4083:
4062:(10): 629–640.
4053:
4052:
4048:
4008:
4007:
4003:
3998:
3994:
3964:
3963:
3959:
3923:
3922:
3918:
3908:
3907:
3903:
3859:
3858:
3854:
3810:
3809:
3805:
3783:
3782:
3775:
3765:
3763:
3762:on 16 June 2010
3759:
3736:
3731:
3730:
3726:
3688:
3687:
3683:
3675:
3667:
3666:
3662:
3624:
3623:
3619:
3590:(10): 879–891.
3580:
3579:
3575:
3545:
3544:
3540:
3518:
3517:
3513:
3508:Wayback Machine
3498:
3494:
3485:
3484:
3480:
3470:
3468:
3464:
3457:
3452:
3451:
3447:
3412:Pharmacotherapy
3409:
3408:
3399:
3377:
3376:
3372:
3362:
3360:
3356:
3351:
3350:
3346:
3308:
3307:
3303:
3296:
3281:
3280:
3276:
3266:
3264:
3247:
3246:
3242:
3206:
3205:
3201:
3179:
3178:
3174:
3138:
3137:
3133:
3095:
3094:
3090:
3059:
3058:
3054:
3018:
3017:
3013:
3000:
2999:
2995:
2965:
2964:
2955:
2945:
2943:
2928:
2927:
2923:
2887:
2886:
2879:
2843:
2842:
2838:
2802:
2801:
2797:
2789:
2784:
2783:
2776:
2740:
2739:
2735:
2725:
2723:
2714:
2713:
2709:
2665:
2664:
2660:
2616:
2615:
2611:
2573:
2572:
2568:
2538:
2537:
2533:
2495:
2494:
2490:
2460:
2459:
2455:
2411:
2410:
2403:
2365:
2364:
2353:
2317:
2316:
2309:
2299:
2297:
2289:
2288:
2284:
2271:
2270:
2266:
2256:
2254:
2249:
2248:
2244:
2208:
2207:
2203:
2167:
2166:
2162:
2145:
2118:
2117:
2113:
2075:
2074:
2070:
2062:
2058:
2057:
2053:
2014:
2013:
2009:
1979:
1978:
1974:
1945:(10): 957–965.
1932:
1931:
1927:
1883:
1882:
1878:
1842:
1841:
1837:
1793:
1792:
1788:
1778:
1777:
1773:
1756:
1747:
1744:
1688:
1622:
1571:
1514:
1473:
1405:
1340:
1326:
1317:
1312:
1307:
1302:
1297:
1292:
1287:
1282:
1277:
1272:
1267:
1253:
1246:
1241:
1236:
1231:
1226:
1221:
1216:
1211:
1206:
1201:
1189:
1184:
1179:
1174:
1169:
1164:
1159:
1154:
1149:
1144:
1139:
1085:
1076:
1067:
1060:
1053:
1046:
1041:
1036:
1029:
1024:
1017:
1005:
1000:
995:
990:
985:
980:
975:
970:
965:
960:
955:
942:
932:
918:
909:
903:
900:
891:
888:
885:
876:
873:
864:
862:
854:
852:
842:
833:
817:
798:
759:
757:Cellular uptake
717:DNA replication
705:
621:
611:
569:QT prolongation
553:
545:cytochrome P450
478:
471:
466:
384:
365:
353:Marfan syndrome
348:
339:
331:Achilles tendon
326:
313:low blood sugar
304:
296:
294:Adverse effects
266:cystic fibrosis
253:
192:
119:
60:
28:
23:
22:
15:
12:
11:
5:
6121:
6119:
6111:
6110:
6100:
6099:
6093:
6092:
6089:
6088:
6087:
6086:
6083:
6072:
6066:
6060:
6059:
6056:
6055:
6052:
6051:
6049:
6048:
6042:
6040:
6034:
6033:
6031:
6030:
6025:
6020:
6015:
6010:
6004:
6002:
6000:RNA polymerase
5988:
5981:
5980:
5977:
5976:
5974:
5973:
5967:
5965:
5962:Nitroimidazole
5955:
5944:
5943:
5940:
5939:
5937:
5936:
5930:Aminocoumarins
5926:
5924:
5916:
5915:
5913:
5912:
5907:
5901:
5899:
5895:
5894:
5891:
5890:
5888:
5887:
5882:
5877:
5872:
5867:
5862:
5857:
5852:
5846:
5844:
5838:
5837:
5835:
5834:
5832:Alatrofloxacin
5825:
5820:
5815:
5810:
5805:
5800:
5795:
5790:
5785:
5780:
5774:
5772:
5770:4th generation
5766:
5765:
5763:
5762:
5757:
5752:
5747:
5742:
5737:
5732:
5726:
5724:
5722:3rd generation
5718:
5717:
5715:
5714:
5709:
5704:
5699:
5686:
5681:
5676:
5671:
5666:
5660:
5658:
5656:2nd generation
5649:
5643:
5642:
5640:
5639:
5634:
5632:Piromidic acid
5629:
5627:Pipemidic acid
5624:
5619:
5617:Nalidixic acid
5614:
5609:
5603:
5601:
5599:1st generation
5592:
5567:
5566:
5563:
5562:
5560:
5559:
5554:
5549:
5544:
5538:
5536:
5532:
5531:
5529:
5528:
5523:
5518:
5513:
5507:
5505:
5501:
5500:
5497:
5496:
5494:
5493:
5488:
5483:
5481:Sulfaguanidine
5478:
5476:Sulfadicramide
5473:
5468:
5463:
5457:
5455:
5451:
5450:
5448:
5447:
5442:
5440:Sulfaphenazole
5437:
5432:
5427:
5422:
5417:
5412:
5407:
5402:
5396:
5394:
5388:
5387:
5385:
5384:
5379:
5374:
5368:
5366:
5360:
5359:
5357:
5356:
5351:
5337:
5336:
5335:
5325:
5315:
5305:
5300:
5298:Sulfamethizole
5295:
5289:
5287:
5278:
5275:DHPS inhibitor
5266:
5265:
5263:
5262:
5261:
5260:
5255:
5250:
5245:
5240:
5235:
5224:
5222:
5220:DHFR inhibitor
5213:
5194:
5193:
5177:Antibacterials
5175:
5173:
5172:
5165:
5158:
5150:
5144:
5143:
5137:
5124:
5115:
5109:
5085:
5081:
5080:External links
5078:
5075:
5074:
5047:
5033:
5021:Gupta (2009).
5013:
4988:
4950:
4927:(3): 455–464.
4884:
4873:on 6 June 2011
4849:
4808:
4799:
4770:
4742:
4718:
4694:
4668:
4665:on 9 May 2017.
4644:
4619:
4604:
4589:
4568:
4541:(6): 437–465.
4525:
4476:
4441:
4422:(4): 417–427.
4406:
4391:
4386:The quinolones
4376:
4316:
4275:
4261:10.1086/428051
4231:
4182:
4153:(2): 337–341.
4130:
4081:
4046:
4021:(7): 885–888.
4001:
3992:
3973:(3): 259–268.
3957:
3943:10.1086/512369
3936:(7): 977–980.
3916:
3901:
3872:(3): 380–384.
3852:
3829:10.1086/511159
3803:
3773:
3724:
3681:
3660:
3617:
3573:
3538:
3511:
3492:
3478:
3467:on 6 July 2017
3445:
3397:
3370:
3344:
3301:
3294:
3274:
3240:
3219:(4): 593–596.
3199:
3188:(4): 191–197.
3172:
3158:10.1086/591126
3151:(6): 735–743.
3131:
3104:(5): 359–378.
3088:
3052:
3031:(4): 370–378.
3011:
2993:
2974:(4): 371–384.
2953:
2921:
2907:10.1086/428055
2877:
2836:
2815:(4): 881–891.
2795:
2774:
2733:
2707:
2678:(3): 264–272.
2658:
2609:
2566:
2531:
2488:
2469:(3): 211–216.
2453:
2424:(3): 422–427.
2401:
2374:(9): 709–721.
2351:
2307:
2282:
2279:. 12 May 2016.
2264:
2242:
2201:
2180:(6): 459–462.
2160:
2127:(6): 524–531.
2123:(in Spanish).
2111:
2084:(5): 431–435.
2068:
2051:
2024:(4): 388–416.
2007:
1972:
1925:
1896:(2): 247–274.
1876:
1835:
1786:
1781:The Quinolones
1770:
1769:
1743:
1740:
1739:
1738:
1732:
1726:
1720:
1714:
1708:
1702:
1687:
1686:Veterinary use
1684:
1683:
1682:
1662:
1661:
1656:
1651:
1646:
1641:
1636:
1631:
1621:
1618:
1610:
1609:
1604:
1599:
1594:
1589:
1584:
1570:
1567:
1559:
1558:
1553:
1548:
1543:
1538:
1533:
1528:
1523:
1513:
1510:
1507:pipemidic acid
1503:piromidic acid
1499:nalidixic acid
1491:
1490:
1485:
1480:
1472:
1469:
1404:
1401:
1377:pipemidic acid
1356:nalidixic acid
1339:
1336:
1333:
1332:
1324:
1320:
1319:
1314:
1309:
1304:
1299:
1294:
1289:
1284:
1279:
1274:
1269:
1264:
1258:
1257:
1248:
1243:
1238:
1233:
1228:
1223:
1218:
1213:
1208:
1203:
1198:
1192:
1191:
1186:
1181:
1176:
1171:
1166:
1161:
1156:
1151:
1146:
1141:
1136:
1130:
1129:
1126:
1123:
1120:
1117:
1114:
1111:
1108:
1105:
1102:
1099:
1096:
1090:
1089:
1080:
1071:
1064:
1057:
1048:
1043:
1038:
1031:
1026:
1019:
1014:
1008:
1007:
1002:
997:
992:
987:
982:
977:
972:
967:
962:
957:
952:
946:
945:
935:
924:
923:
920:
913:
905:
893:
883:
878:
866:
860:
856:
850:
846:
835:
828:
816:
813:
797:
794:
758:
755:
704:
701:
610:
607:
552:
549:
477:
474:
469:
465:
462:
458:kidney failure
407:cephalosporins
383:
380:
364:
361:
347:
344:
338:
337:Nervous system
335:
325:
322:
303:
302:Boxed warnings
300:
295:
292:
264:infections in
252:
249:
217:pyelonephritis
191:
188:
149:bacteriocidals
146:broad-spectrum
137:
136:
130:
129:
125:
124:
117:
111:
110:
109:External links
106:
105:
98:
92:
91:
87:
86:
81:
75:
74:
71:
67:
66:
62:
61:
54:
46:
45:
37:
36:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6120:
6109:
6106:
6105:
6103:
6084:
6082:
6079:
6078:
6076:
6073:
6070:
6067:
6065:
6062:
6061:
6057:
6047:
6044:
6043:
6041:
6039:
6035:
6029:
6026:
6024:
6021:
6019:
6016:
6014:
6011:
6009:
6006:
6005:
6003:
6001:
5996:
5992:
5989:
5986:
5982:
5972:
5969:
5968:
5966:
5963:
5959:
5956:
5954:
5949:
5945:
5935:
5931:
5928:
5927:
5925:
5922:
5917:
5911:
5908:
5906:
5903:
5902:
5900:
5896:
5886:
5883:
5881:
5880:Pradofloxacin
5878:
5876:
5873:
5871:
5870:Marbofloxacin
5868:
5866:
5863:
5861:
5858:
5856:
5853:
5851:
5848:
5847:
5845:
5843:
5839:
5833:
5829:
5828:Trovafloxacin
5826:
5824:
5821:
5819:
5818:Prulifloxacin
5816:
5814:
5811:
5809:
5808:Clinafloxacin
5806:
5804:
5801:
5799:
5796:
5794:
5791:
5789:
5786:
5784:
5781:
5779:
5776:
5775:
5773:
5771:
5767:
5761:
5758:
5756:
5753:
5751:
5748:
5746:
5743:
5741:
5740:Grepafloxacin
5738:
5736:
5733:
5731:
5728:
5727:
5725:
5723:
5719:
5713:
5710:
5708:
5705:
5703:
5700:
5698:
5694:
5690:
5687:
5685:
5682:
5680:
5677:
5675:
5672:
5670:
5667:
5665:
5664:Ciprofloxacin
5662:
5661:
5659:
5657:
5653:
5650:
5648:
5644:
5638:
5635:
5633:
5630:
5628:
5625:
5623:
5622:Oxolinic acid
5620:
5618:
5615:
5613:
5610:
5608:
5605:
5604:
5602:
5600:
5596:
5593:
5590:
5583:
5578:
5577:topoisomerase
5572:
5568:
5558:
5555:
5553:
5550:
5548:
5545:
5543:
5542:Acediasulfone
5540:
5539:
5537:
5533:
5527:
5524:
5522:
5519:
5517:
5514:
5512:
5509:
5508:
5506:
5502:
5492:
5489:
5487:
5484:
5482:
5479:
5477:
5474:
5472:
5469:
5467:
5466:Sulfacetamide
5464:
5462:
5459:
5458:
5456:
5452:
5446:
5443:
5441:
5438:
5436:
5435:Sulfamerazine
5433:
5431:
5428:
5426:
5423:
5421:
5418:
5416:
5413:
5411:
5408:
5406:
5403:
5401:
5398:
5397:
5395:
5393:
5389:
5383:
5380:
5378:
5375:
5373:
5370:
5369:
5367:
5365:
5361:
5355:
5354:Sulfathiourea
5352:
5349:
5345:
5341:
5340:Sulfathiazole
5338:
5334:
5331:
5330:
5329:
5328:Sulfanilamide
5326:
5323:
5319:
5318:Sulfafurazole
5316:
5313:
5312:Sulfasalazine
5309:
5308:Sulfapyridine
5306:
5304:
5303:Sulfadimidine
5301:
5299:
5296:
5294:
5291:
5290:
5288:
5286:
5282:
5279:
5276:
5271:
5267:
5259:
5256:
5254:
5251:
5249:
5248:Pyrimethamine
5246:
5244:
5241:
5239:
5236:
5234:
5231:
5230:
5229:
5226:
5225:
5223:
5221:
5217:
5214:
5205:
5199:
5195:
5190:
5186:
5182:
5178:
5171:
5166:
5164:
5159:
5157:
5152:
5151:
5148:
5141:
5138:
5135:
5131:
5128:
5125:
5123:
5119:
5116:
5113:
5110:
5108:
5104:
5099:
5095:
5094:
5089:
5084:
5083:
5079:
5062:
5058:
5051:
5048:
5036:
5030:
5026:
5025:
5017:
5014:
4998:
4992:
4989:
4976:
4972:
4968:
4961:
4959:
4957:
4955:
4951:
4938:
4934:
4930:
4926:
4922:
4918:
4911:
4909:
4907:
4905:
4903:
4901:
4899:
4897:
4895:
4893:
4891:
4889:
4885:
4872:
4868:
4864:
4860:
4853:
4850:
4845:
4841:
4836:
4831:
4827:
4823:
4819:
4812:
4809:
4803:
4800:
4784:
4780:
4774:
4771:
4759:
4758:
4753:
4746:
4743:
4735:
4728:
4722:
4719:
4711:
4704:
4698:
4695:
4682:
4678:
4672:
4669:
4661:
4654:
4648:
4645:
4640:
4636:
4630:
4628:
4626:
4624:
4620:
4615:
4608:
4605:
4600:
4593:
4590:
4582:
4578:
4572:
4569:
4564:
4560:
4556:
4552:
4548:
4544:
4540:
4536:
4529:
4526:
4510:
4506:
4502:
4498:
4494:
4487:
4480:
4477:
4472:
4468:
4464:
4460:
4456:
4452:
4445:
4442:
4437:
4433:
4429:
4425:
4421:
4417:
4410:
4407:
4402:
4395:
4392:
4387:
4380:
4377:
4372:
4368:
4363:
4358:
4354:
4350:
4346:
4342:
4338:
4334:
4330:
4323:
4321:
4317:
4312:
4308:
4303:
4298:
4294:
4290:
4286:
4279:
4276:
4271:
4267:
4262:
4257:
4253:
4249:
4245:
4238:
4236:
4232:
4227:
4223:
4218:
4213:
4209:
4205:
4201:
4197:
4193:
4186:
4183:
4178:
4174:
4169:
4164:
4160:
4156:
4152:
4148:
4144:
4137:
4135:
4131:
4126:
4122:
4117:
4112:
4108:
4104:
4100:
4096:
4092:
4085:
4082:
4077:
4073:
4069:
4065:
4061:
4057:
4050:
4047:
4043:
4038:
4034:
4029:
4024:
4020:
4016:
4012:
4005:
4002:
3996:
3993:
3988:
3984:
3980:
3976:
3972:
3968:
3961:
3958:
3953:
3949:
3944:
3939:
3935:
3931:
3927:
3920:
3917:
3912:
3905:
3902:
3897:
3893:
3888:
3883:
3879:
3875:
3871:
3867:
3863:
3856:
3853:
3848:
3844:
3839:
3834:
3830:
3826:
3822:
3818:
3814:
3807:
3804:
3799:
3795:
3791:
3787:
3780:
3778:
3774:
3758:
3754:
3750:
3746:
3742:
3735:
3728:
3725:
3720:
3716:
3712:
3708:
3704:
3700:
3696:
3692:
3685:
3682:
3674:
3670:
3664:
3661:
3656:
3652:
3648:
3644:
3640:
3636:
3632:
3628:
3621:
3618:
3613:
3609:
3605:
3601:
3597:
3593:
3589:
3585:
3577:
3574:
3569:
3565:
3561:
3557:
3553:
3549:
3542:
3539:
3534:
3530:
3526:
3522:
3515:
3512:
3509:
3505:
3501:
3500:2011 Document
3496:
3493:
3488:
3482:
3479:
3463:
3456:
3449:
3446:
3441:
3437:
3433:
3429:
3425:
3421:
3417:
3413:
3406:
3404:
3402:
3398:
3393:
3389:
3385:
3382:(in French).
3381:
3374:
3371:
3355:
3348:
3345:
3340:
3336:
3332:
3328:
3324:
3320:
3316:
3312:
3305:
3302:
3297:
3291:
3287:
3286:
3278:
3275:
3263:
3259:
3255:
3251:
3244:
3241:
3236:
3232:
3227:
3222:
3218:
3214:
3210:
3203:
3200:
3195:
3191:
3187:
3183:
3176:
3173:
3168:
3164:
3159:
3154:
3150:
3146:
3142:
3135:
3132:
3127:
3123:
3119:
3115:
3111:
3107:
3103:
3099:
3092:
3089:
3084:
3080:
3076:
3072:
3068:
3064:
3056:
3053:
3048:
3044:
3039:
3034:
3030:
3026:
3022:
3015:
3012:
3007:
3003:
2997:
2994:
2989:
2985:
2981:
2977:
2973:
2969:
2962:
2960:
2958:
2954:
2941:
2937:
2936:
2931:
2925:
2922:
2917:
2913:
2908:
2903:
2899:
2895:
2891:
2884:
2882:
2878:
2873:
2869:
2864:
2859:
2855:
2851:
2847:
2840:
2837:
2832:
2828:
2823:
2818:
2814:
2810:
2806:
2799:
2796:
2788:
2781:
2779:
2775:
2770:
2766:
2761:
2756:
2752:
2748:
2744:
2737:
2734:
2721:
2717:
2711:
2708:
2703:
2699:
2694:
2689:
2685:
2681:
2677:
2673:
2669:
2662:
2659:
2654:
2650:
2645:
2640:
2636:
2632:
2629:(7084): 869.
2628:
2624:
2620:
2613:
2610:
2605:
2601:
2597:
2593:
2589:
2585:
2581:
2577:
2570:
2567:
2562:
2558:
2554:
2550:
2546:
2542:
2535:
2532:
2527:
2523:
2519:
2515:
2511:
2507:
2503:
2499:
2492:
2489:
2484:
2480:
2476:
2472:
2468:
2464:
2457:
2454:
2449:
2445:
2440:
2435:
2431:
2427:
2423:
2419:
2415:
2408:
2406:
2402:
2397:
2393:
2389:
2385:
2381:
2377:
2373:
2369:
2362:
2360:
2358:
2356:
2352:
2347:
2343:
2338:
2333:
2329:
2325:
2321:
2314:
2312:
2308:
2296:
2292:
2286:
2283:
2278:
2274:
2268:
2265:
2252:
2246:
2243:
2238:
2234:
2229:
2224:
2220:
2216:
2212:
2205:
2202:
2197:
2193:
2188:
2183:
2179:
2175:
2171:
2164:
2161:
2156:
2150:
2142:
2138:
2134:
2130:
2126:
2122:
2115:
2112:
2107:
2103:
2099:
2095:
2091:
2087:
2083:
2079:
2072:
2069:
2061:
2055:
2052:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2011:
2008:
2003:
1999:
1995:
1991:
1987:
1983:
1976:
1973:
1968:
1964:
1960:
1956:
1952:
1948:
1944:
1940:
1936:
1929:
1926:
1921:
1917:
1912:
1907:
1903:
1899:
1895:
1891:
1887:
1880:
1877:
1872:
1868:
1863:
1858:
1854:
1850:
1846:
1839:
1836:
1831:
1827:
1822:
1817:
1813:
1809:
1805:
1801:
1797:
1790:
1787:
1782:
1775:
1772:
1768:
1765:
1761:
1760:
1754:
1741:
1736:
1733:
1730:
1727:
1724:
1723:marbofloxacin
1721:
1718:
1715:
1712:
1709:
1706:
1703:
1700:
1697:
1696:
1695:
1693:
1685:
1681:
1678:
1677:
1676:
1673:
1671:
1670:trovafloxacin
1667:
1660:
1657:
1655:
1652:
1650:
1649:prulifloxacin
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1629:clinafloxacin
1627:
1626:
1625:
1619:
1617:
1615:
1608:
1605:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1587:grepafloxacin
1585:
1583:
1580:
1579:
1578:
1576:
1568:
1566:
1564:
1557:
1554:
1552:
1549:
1547:
1544:
1542:
1539:
1537:
1534:
1532:
1529:
1527:
1524:
1522:
1521:ciprofloxacin
1519:
1518:
1517:
1511:
1509:
1508:
1504:
1500:
1496:
1489:
1486:
1484:
1483:oxolinic acid
1481:
1478:
1475:
1474:
1470:
1468:
1466:
1462:
1461:ciprofloxacin
1458:
1453:
1451:
1442:
1438:
1432:
1428:
1426:
1423:
1419:
1415:
1411:
1402:
1400:
1396:
1392:
1388:
1386:
1382:
1381:oxolinic acid
1378:
1374:
1369:
1365:
1361:
1357:
1349:
1348:naphthyridine
1344:
1337:
1315:
1310:
1305:
1300:
1295:
1290:
1285:
1280:
1275:
1270:
1265:
1263:
1260:
1259:
1249:
1244:
1239:
1234:
1229:
1224:
1219:
1214:
1209:
1204:
1199:
1197:
1194:
1193:
1187:
1182:
1177:
1172:
1167:
1162:
1157:
1152:
1147:
1142:
1137:
1135:
1132:
1131:
1127:
1124:
1121:
1118:
1115:
1112:
1109:
1106:
1103:
1100:
1097:
1095:
1092:
1091:
1081:
1072:
1065:
1058:
1049:
1044:
1039:
1032:
1027:
1020:
1015:
1013:
1010:
1009:
1003:
998:
993:
988:
983:
978:
973:
968:
963:
958:
953:
951:
950:Ciprofloxacin
948:
947:
941:
936:
931:
926:
925:
919:unchanged (%)
917:
911:
899:
887:
872:
863:
853:
841:
832:
827:
823:
814:
812:
810:
807:
803:
802:pharmacophore
795:
793:
791:
785:
783:
782:
777:
776:
771:
768:
767:intracellular
764:
756:
754:
752:
748:
742:
739:
738:
733:
729:
726:
722:
718:
709:
702:
700:
698:
694:
690:
686:
682:
677:
675:
671:
667:
662:
660:
659:
654:
650:
646:
644:
643:
637:
633:
628:
627:
620:
616:
608:
606:
604:
600:
599:antibacterial
596:
593:
589:
585:
584:pharmacophore
580:
578:
574:
570:
566:
562:
558:
550:
548:
546:
542:
538:
533:
531:
527:
523:
519:
515:
511:
507:
503:
499:
495:
491:
487:
483:
475:
473:
463:
461:
459:
454:
452:
447:
445:
441:
440:
435:
430:
428:
424:
420:
416:
412:
408:
402:
398:
396:
392:
391:
381:
379:
377:
372:
370:
362:
360:
358:
354:
345:
343:
336:
334:
332:
323:
321:
318:
314:
309:
301:
299:
293:
291:
289:
283:
280:
275:
271:
267:
263:
259:
250:
248:
245:
243:
242:tetracyclines
239:
238:
233:
232:osteomyelitis
229:
224:
222:
219:or bacterial
218:
210:
209:Trovafloxacin
206:
200:
196:
189:
187:
185:
184:ciprofloxacin
181:
180:Gram-positive
177:
176:Gram-negative
173:
169:
164:
162:
158:
154:
151:that share a
150:
147:
143:
135:
131:
126:
122:
118:
116:
112:
107:
103:
99:
97:
93:
90:Clinical data
88:
85:
82:
80:
76:
72:
68:
63:
58:
52:
47:
44:
43:
38:
33:
30:
19:
6038:Lipiarmycins
5885:Sarafloxacin
5875:Orbifloxacin
5860:Enrofloxacin
5850:Danofloxacin
5823:Sitafloxacin
5803:Moxifloxacin
5798:Gemifloxacin
5793:Finafloxacin
5788:Gatifloxacin
5783:Delafloxacin
5778:Besifloxacin
5760:Tosufloxacin
5755:Temafloxacin
5750:Sparfloxacin
5745:Pazufloxacin
5735:Balofloxacin
5730:Levofloxacin
5689:Nadifloxacin
5684:Lomefloxacin
5646:
5570:
5504:Combinations
5486:Sulfametrole
5471:Sulfaclozine
5377:Sulfadiazine
5285:Short-acting
5270:Sulfonamides
5258:Trimethoprim
5091:
5065:. Retrieved
5061:the original
5050:
5040:20 September
5038:. Retrieved
5023:
5016:
5004:. Retrieved
4991:
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4970:
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4871:the original
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4773:
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4697:
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4671:
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4647:
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4499:(1): 49–56.
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3757:the original
3747:(1): 49–56.
3744:
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3697:(1): 15–21.
3694:
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3630:
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3554:(2): 75–78.
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3462:the original
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3347:
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2933:
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2812:
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2724:. Retrieved
2719:
2710:
2675:
2672:JAMA Surgery
2671:
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2245:
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2149:cite journal
2124:
2120:
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1985:
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1928:
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1879:
1852:
1848:
1838:
1803:
1799:
1789:
1780:
1774:
1758:
1745:
1735:sarafloxacin
1729:orbifloxacin
1711:enrofloxacin
1699:danofloxacin
1689:
1674:
1666:gemifloxacin
1663:
1659:delafloxacin
1654:besifloxacin
1644:sitafloxacin
1639:moxifloxacin
1634:gatifloxacin
1623:
1614:tosufloxacin
1611:
1607:temafloxacin
1602:sparfloxacin
1597:pazufloxacin
1592:levofloxacin
1582:balofloxacin
1575:streptococci
1572:
1560:
1536:nadifloxacin
1531:lomefloxacin
1515:
1492:
1465:levofloxacin
1457:moxifloxacin
1454:
1446:
1406:
1397:
1393:
1389:
1353:
1262:Moxifloxacin
1196:Levofloxacin
1134:Gemifloxacin
1094:Gatifloxacin
799:
796:Pharmacology
786:
779:
773:
760:
743:
736:
714:
678:
670:otitis media
663:
656:
655:, including
647:
640:
635:
625:
622:
602:
581:
554:
534:
526:pyrazinamide
518:cyclosporine
502:theophylline
479:
476:Interactions
467:
455:
448:
437:
431:
423:sulfonamides
403:
399:
388:
385:
375:
368:
366:
349:
340:
327:
305:
297:
284:
270:azithromycin
254:
246:
235:
225:
213:
199:Levofloxacin
190:Medical uses
167:
165:
141:
140:
128:Legal status
102:Drug Classes
40:
29:
6071:from market
6046:Fidaxomicin
6018:Rifapentine
5971:Secnidazole
5964:derivatives
5905:Nemonoxacin
5865:Ibafloxacin
5813:Garenoxacin
5702:Norfloxacin
5552:Solasulfone
5491:Sulfanitran
5445:Sulfamazone
5405:Sulfadoxine
5392:Long-acting
5382:Sulfamoxole
5253:Tetroxoprim
5233:Brodimoprim
5210:DNA and RNA
5198:Antifolates
5086:‹ The
3527:(1): 8–15.
3098:Drug Safety
2946:16 December
2368:Drug Safety
1717:ibafloxacin
1541:norfloxacin
1450:fluorinated
1437:cyclopropyl
1414:chloroquine
1403:Generations
1368:chloroquine
1012:Garenoxacin
877:(μg • h/mL)
530:cycloserine
434:QT interval
419:clindamycin
415:penicillins
376:Clostridium
274:ceftriaxone
262:pseudomonal
221:prostatitis
157:4-quinolone
134:In Wikidata
6008:Rifampicin
5995:Rifamycins
5953:inhibitors
5934:Novobiocin
5910:Ozenoxacin
5855:Difloxacin
5842:Veterinary
5712:Rufloxacin
5707:Pefloxacin
5679:Fleroxacin
5612:Flumequine
5582:DNA gyrase
5571:Quinolones
5430:Sulfaperin
5243:Ormetoprim
5212:synthesis)
4788:. USA: FDA
4763:6 November
4687:19 October
2726:9 February
2215:Pediatrics
1742:References
1705:difloxacin
1680:ozenoxacin
1556:rufloxacin
1551:pefloxacin
1526:fleroxacin
1477:flumequine
1441:piperazine
1410:distillate
1364:distillate
800:The basic
693:DNA gyrase
685:DNA gyrase
649:Resistance
613:See also:
582:The basic
498:cimetidine
494:probenecid
490:sucralfate
444:arrhythmia
427:vancomycin
411:macrolides
237:Salmonella
161:infections
42:Drug class
6081:Phase III
6069:Withdrawn
6028:Rifalazil
6023:Rifaximin
6013:Rifabutin
5987:synthesis
5948:Anaerobic
5919:Related (
5669:Ofloxacin
5637:Rosoxacin
5607:Cinoxacin
5557:Sulfoxone
5410:Sulfalene
5333:Prontosil
5120:from the
3363:31 August
3267:24 August
3262:0362-4331
1959:2376-6980
1546:ofloxacin
1495:cinoxacin
1488:rosoxacin
1385:cinoxacin
770:pathogens
689:mutations
653:pathogens
632:macrolide
588:quinoline
514:phenytoin
234:from the
96:Drugs.com
57:quinolone
35:Quinolone
6102:Category
5674:Enoxacin
5461:Mafenide
5238:Iclaprim
5130:Archived
5088:template
4975:Archived
4937:Archived
4933:11858629
4877:18 March
4844:10997595
4563:26955572
4555:17154673
4509:Archived
4371:22517853
4270:15942877
4226:24576155
4177:11294736
4076:17008172
4037:12588273
3987:15745724
3952:17342653
3896:15757551
3847:17278083
3719:31447696
3711:15659258
3655:37437573
3647:16470165
3612:26457648
3604:17901792
3568:19181435
3533:12700435
3504:Archived
3440:29617455
3432:11642691
3392:11859676
3339:34091286
3331:17559736
3235:11909831
3194:23570031
3167:18694344
3126:19026852
3118:19419232
3083:17165634
3047:22489673
2988:11172695
2916:15942881
2872:22921930
2831:24324224
2769:23620467
2702:33404647
2604:26411679
2596:17911203
2561:16876974
2526:36759747
2518:24259701
2483:15661570
2448:24762232
2396:24948660
2388:23888427
2346:39053916
2237:21949152
2196:18072993
2141:21132249
2106:52835801
2098:22189521
2046:14907563
2038:15699079
2002:15993673
1967:29028464
1920:20738404
1871:12702698
1830:12821463
1563:enoxacin
1422:fluorine
916:Excreted
806:fluorine
772:such as
725:fluorine
592:fluorine
557:epilepsy
522:rifampin
506:warfarin
486:antacids
378:strain.
251:Children
172:fluorine
79:ATC code
5580:and/or
5547:Dapsone
5090:below (
4471:1469702
4436:6309236
4362:3357493
4341:Bibcode
4333:Science
4311:1320012
4217:3985860
4168:2631735
4125:9661020
3887:3298265
3838:7107997
3471:24 July
2693:7788511
2653:9093098
2644:2126221
2623:The BMJ
2439:4080593
2300:13 July
2295:fda.gov
1911:3053476
1373:analogs
1338:History
939:Hepatic
910:binding
908:Protein
855:(μg/mL)
737:-oxacin
605:1997).
482:cations
371:colitis
363:Colitis
324:Tendons
258:anthrax
121:D015363
6064:WHO-EM
5107:Curlie
5093:Curlie
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1821:161843
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1383:, and
904:(L/kg)
831:Dosage
763:porins
681:efflux
573:stroke
528:, and
5179:that
5067:1 May
5006:6 May
5000:(PDF)
4981:6 May
4943:6 May
4792:6 May
4786:(PDF)
4737:(PDF)
4730:(PDF)
4713:(PDF)
4706:(PDF)
4663:(PDF)
4656:(PDF)
4584:(PDF)
4559:S2CID
4518:6 May
4512:(PDF)
4489:(PDF)
3766:6 May
3760:(PDF)
3737:(PDF)
3715:S2CID
3676:(PDF)
3651:S2CID
3608:S2CID
3465:(PDF)
3458:(PDF)
3436:S2CID
3357:(PDF)
3335:S2CID
3122:S2CID
2600:S2CID
2522:S2CID
2392:S2CID
2102:S2CID
2063:(PDF)
2042:S2CID
1755:from
929:Renal
603:circa
425:, or
382:Other
5189:J01M
5185:J01E
5069:2006
5042:2010
5029:ISBN
5008:2011
4983:2011
4945:2011
4929:PMID
4879:2008
4840:PMID
4794:2011
4765:2015
4689:2015
4551:PMID
4520:2011
4467:PMID
4432:PMID
4367:PMID
4307:PMID
4266:PMID
4222:PMID
4173:PMID
4121:PMID
4072:PMID
4033:PMID
4015:JAMA
3983:PMID
3948:PMID
3892:PMID
3843:PMID
3768:2011
3707:PMID
3643:PMID
3600:PMID
3564:PMID
3529:PMID
3473:2017
3428:PMID
3388:PMID
3365:2009
3327:PMID
3290:ISBN
3269:2021
3258:ISSN
3231:PMID
3190:PMID
3163:PMID
3114:PMID
3079:PMID
3043:PMID
2984:PMID
2948:2019
2912:PMID
2868:PMID
2827:PMID
2765:PMID
2728:2019
2698:PMID
2649:PMID
2592:PMID
2557:PMID
2514:PMID
2479:PMID
2444:PMID
2384:PMID
2342:PMID
2302:2018
2259:2008
2233:PMID
2192:PMID
2174:CJEM
2155:link
2137:PMID
2094:PMID
2034:PMID
1998:PMID
1963:PMID
1955:ISSN
1916:PMID
1867:PMID
1826:PMID
1668:and
1425:atom
1327:and
1293:12.1
1291:12.1
1288:33.8
1286:15.4
1278:3.34
1276:1.16
1222:82.0
1220:48.0
1212:7.13
1210:5.08
1160:15.9
1150:2.29
1148:1.19
1110:33.8
1104:3.86
1045:14.2
1042:96.7
1030:10.4
976:14.0
974:10.1
966:3.00
964:2.30
897:Vd/F
834:(mg)
826:Drug
809:atom
778:and
728:atom
617:and
595:atom
355:and
315:and
260:and
178:and
115:MeSH
84:J01M
5985:RNA
5950:DNA
5114:CDC
5105:at
4830:doi
4639:FDA
4543:doi
4501:doi
4459:doi
4424:doi
4420:740
4357:PMC
4349:doi
4337:336
4297:doi
4293:267
4256:doi
4212:PMC
4204:doi
4163:PMC
4155:doi
4111:PMC
4103:doi
4064:doi
4023:doi
4019:289
3975:doi
3971:118
3938:doi
3882:PMC
3874:doi
3833:PMC
3825:doi
3794:doi
3749:doi
3699:doi
3635:doi
3592:doi
3556:doi
3552:143
3420:doi
3319:doi
3221:doi
3153:doi
3106:doi
3071:doi
3033:doi
2976:doi
2902:doi
2858:doi
2817:doi
2755:doi
2720:FDA
2688:PMC
2680:doi
2676:156
2639:PMC
2631:doi
2627:314
2584:doi
2549:doi
2506:doi
2471:doi
2434:PMC
2426:doi
2376:doi
2332:doi
2277:FDA
2223:doi
2219:128
2182:doi
2129:doi
2125:108
2086:doi
2026:doi
2022:171
1990:doi
1986:118
1947:doi
1906:PMC
1898:doi
1857:doi
1816:PMC
1808:doi
1329:AUC
1325:max
1318:No
1298:3.3
1296:3.3
1283:1.7
1281:1.7
1268:400
1266:200
1247:Yes
1245:Yes
1232:1.1
1230:1.1
1227:6.9
1225:6.9
1217:1.7
1215:1.7
1202:750
1200:500
1190:No
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1168:3.5
1165:8.0
1163:8.0
1158:7.3
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1153:1.2
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1138:320
1128:No
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1113:8.0
1107:1.5
1098:400
1047:9.8
1037:1.2
1028:5.0
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1016:400
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981:3.5
979:3.5
971:1.2
969:1.2
956:750
954:500
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892:(h)
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865:(h)
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