Quinolone antibiotic

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 195: 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.

205: 51: 1343: 708: 1431: 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)]" 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

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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).

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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

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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

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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

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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

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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

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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

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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

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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.

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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

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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.

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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

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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

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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.

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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 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".

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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".

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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.

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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

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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.

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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".

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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

1752: 4449:

Suto MJ, Domagala JM, Roland GE, Mailloux GB, Cohen MA (December 1992). "Fluoroquinolones: relationships between structural variations, mammalian cell cytotoxicity, and antimicrobial activity".

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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.

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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".

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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

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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 5097: 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".

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Van Bambeke F, Tulkens PM (2009). "Safety profile of the respiratory fluoroquinolone moxifloxacin: comparison with other fluoroquinolones and other antibacterial classes".

5525: 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: 5520: 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

5321: 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" 2154: 1763: 468:

The mechanisms of the toxicity of fluoroquinolones have been attributed to their interactions with different receptor complexes, such as blockade of the GABA

78: 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

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

5167: 3249: 4850: 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: 3001: 460:

and seizure. Susceptible groups of patients, such as children and the elderly, are at greater risk of adverse reactions during therapeutic use.

5470: 1796:"Isolation and molecular characterization of nalidixic acid-resistant extraintestinal pathogenic Escherichia coli from retail chicken products" 450: 5117: 2939: 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".

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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. 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" 3784:

Hong CY, Kim SH, Kim YK (22 July 1997). "Novel 5-amino-6-methylquinolone antibacterials: A new class of non-6-fluoroquinolones".

868: 4399:

Bergan T, Dalhoff A, Thorsteinsson SB (July 1985). "A review of the pharmacokinetics and tissue penetration of ciprofloxacin.".

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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

6063: 5160: 5032: 3293: 1624:

Fourth-generation fluoroquinolones act at DNA gyrase and topoisomerase IV. This dual action slows development of resistance.

5274: 1980:

Liu H, Mulholland SG (July 2005). "Appropriate antibiotic treatment of genitourinary infections in hospitalized patients".

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Because the use of broad-spectrum antibiotics encourages the spread of multidrug-resistant strains and the development of

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: 4858: 3309:

Iannini PB (June 2007). "The safety profile of moxifloxacin and other fluoroquinolones in special patient populations".

661:, commonly exhibit resistance. Widespread veterinary usage of quinolones, in particular in Europe, has been implicated. 4936: 3499: 5219: 5121: 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: 6080: 5363: 5153: 624: 17: 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

240:, fluoroquinolones are the "drugs of choice" due to their ability to enter bone tissue without chelating it, as 6107: 735: 5952: 472:

receptor complex within the central nervous system, leading to excitotoxic type effects and oxidative stress.

5510: 5129: 4782: 4580: 367: 5284: 2846:"Risk factors for development of Clostridium difficile infection due to BI/NAP1/027 strain: a meta-analysis" 5999: 5391: 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" 2934: 1757: 287: 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. 5145: 5102: 1387:, which were introduced in the 1970s. They proved to be only marginal improvements over nalidixic acid. 915: 750: 223:

where the person may need to be hospitalised, fluoroquinolones are recommended as first-line therapy.

540: 536: 145: 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

5515: 2250: 1359: 641: 114: 3811:

Mandell LA, Wunderink RG, Anzueto A, Bartlett JG, Campbell GD, Dean NC, et al. (March 2007).

1950: 6068: 5576: 4756: 2741:

Deshpande A, Pasupuleti V, Thota P, Pant C, Rolston DD, Sferra TJ, et al. (September 2013).

5424: 5269: 5180: 2014: 907: 895: 774: 564: 356: 316: 278: 5022: 4485: 3756: 1794:

Johnson JR, Murray AC, Gajewski A, Sullivan M, Snippes P, Kuskowski MA, Smith KE (July 2003).

5347: 5343: 5227: 3668: 2148: 780: 731: 720: 680: 672:, and acute upper respiratory tract infection, according to a study supported in part by the 648: 618: 3461: 711:

Structure of bacterial DNA gyrase complexed with DNA and two ciprofloxacin molecules (green)

4597:

Wentland MP (1993). "In memoriam: George Y. Lesher, PhD". In Hooper DC, Wolfson JS (eds.).

4340: 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" 560: 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

8: 5696: 858: 848: 830: 443: 438: 227: 4344: 3689:

Scherer K, Bircher AJ (January 2005). "Hypersensitivity reactions to fluoroquinolones".

3180:

Heidelbaugh JJ, Holmstrom H (April 2013). "The perils of prescribing fluoroquinolones".

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can decrease their binding affinity to quinolones, decreasing the drugs' effectiveness.

5947: 5419: 4834: 4817: 4558: 4361: 4328: 4216: 4191: 4167: 4142: 3886: 3861: 3837: 3812: 3714: 3650: 3638: 3607: 3435: 3334: 3121: 2743:"Community-associated Clostridium difficile infection and antibiotics: a meta-analysis" 2692: 2667: 2643: 2618: 2599: 2521: 2438: 2413: 2391: 2101: 2041: 1910: 1885: 1350:, it is considered the predecessor of all subsequently developed quinolone antibiotics. 937: 880: 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: 5203: 5028: 4928: 4839: 4550: 4546: 4466: 4431: 4427: 4366: 4306: 4265: 4221: 4172: 4120: 4071: 4032: 3982: 3947: 3891: 3842: 3706: 3642: 3599: 3563: 3528: 3427: 3387: 3378:

Saint F, Salomon L, Cicco A, de la Taille A, Chopin D, Abbou CC (December 2001). "".

3326: 3289: 3257: 3230: 3189: 3162: 3113: 3109: 3078: 3042: 3037: 3020: 2983: 2911: 2867: 2826: 2764: 2715: 2697: 2648: 2591: 2556: 2513: 2478: 2443: 2383: 2341: 2272: 2232: 2191: 2136: 2093: 2033: 1997: 1962: 1954: 1915: 1901: 1866: 1825: 1664:

Two structurally related fourth-generation drugs, but formally not 4-quinolones, are

1372: 789: 614: 389: 307: 152: 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.

5692: 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: 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: 1358:

is considered the first quinolone drug. It was introduced in 1962 for treatment of

927: 696: 665: 657: 576: 509: 101: 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".

5588: 5414: 5133: 5092: 3978: 3595: 3559: 3507: 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

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Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (2006).

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Mehlhorn AJ, Brown DA (November 2007). "Safety concerns with fluoroquinolones".

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Unlike the first and second generations, the third generation is active against

6074: 5961: 5831: 5631: 5626: 5616: 5480: 5475: 5439: 5297: 5112:

Healthcare-associated Infections (HAIs)- Quinolones and the Clinical Laboratory

4966: 4778: 4576: 4504: 3752: 2862: 2845: 2683: 2474: 2119:

Rosanova MT, Lede R, Capurro H, Petrungaro V, Copertari P (December 2010). "".

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Heeb S, Fletcher MP, Chhabra SR, Diggle SP, Williams P, Cámara M (March 2011).

1506: 1502: 1498: 1376: 1355: 457: 216: 4996: 3702: 3019:

Skalsky K, Yahav D, Lador A, Eliakim-Raz N, Leibovici L, Paul M (April 2013).

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to quinolones can evolve rapidly, even during a course of treatment. Numerous

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lead to an emergency department visit more frequently than those treated with

6101: 5929: 5879: 5869: 5827: 5817: 5807: 5739: 5663: 5621: 5541: 5465: 5434: 5353: 5339: 5327: 5317: 5311: 5307: 5302: 5292: 5247: 5118:

Information for Healthcare Professionals: Fluoroquinolone Antimicrobial Drugs

5087: 4870: 3322: 3261: 2979: 2634: 2509: 1958: 1722: 1669: 1648: 1628: 1586: 1520: 1482: 1460: 1380: 1347: 949: 801: 766: 598: 583: 406: 394: 241: 231: 208: 183: 179: 175: 148: 83: 4916: 4352: 5884: 5874: 5859: 5849: 5822: 5802: 5797: 5792: 5787: 5782: 5777: 5759: 5754: 5749: 5744: 5734: 5729: 5688: 5683: 5485: 5376: 5257: 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: 1734: 1728: 1710: 1698: 1665: 1658: 1653: 1643: 1638: 1633: 1613: 1606: 1601: 1596: 1591: 1581: 1574: 1535: 1530: 1464: 1456: 1443:

moiety, and the remaining substitution sites (R groups) are hydrogen atoms.

1261: 1195: 1133: 1093: 669: 525: 517: 501: 269: 198: 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: 6045: 6037: 6017: 5970: 5904: 5864: 5812: 5701: 5551: 5490: 5444: 5404: 5381: 5252: 5232: 5176: 5175: 2821: 2804: 2759: 2742: 1861: 1844: 1716: 1540: 1436: 1413: 1367: 1011: 568: 529: 433: 422: 418: 273: 261: 220: 156: 4462: 3625:

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Pharmacokinetics of newer fluoroquinolones following a single oral dose

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Quinolones are chemotherapeutic bactericidal drugs. They interfere with

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first-line agent for community-acquired pneumonia, instead recommending

194: 6007: 5933: 5920: 5909: 5854: 5711: 5706: 5678: 5611: 5581: 5429: 5242: 5197: 3074: 2843: 1704: 1679: 1555: 1550: 1525: 1476: 1440: 1409: 1363: 692: 684: 497: 493: 489: 426: 414: 236: 41: 4207: 3141:"Emergency department visits for antibiotic-associated adverse events" 2587: 586:, or active structure, of the fluoroquinolone class is based upon the 6027: 6022: 6012: 5994: 5668: 5636: 5606: 5556: 5409: 5332: 4327:

Foti JJ, Devadoss B, Winkler JA, Collins JJ, Walker GC (April 2012).

3911:

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The first generation is rarely used. Frequently prescribed drugs are

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antibiotic regimens have failed. However, for serious acute cases of

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3548:

European Journal of Obstetrics, Gynecology, and Reproductive Biology

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Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression

4260: 4243: 3942: 3925: 3828: 3157: 3140: 2906: 2889: 1562: 1449: 1421: 805: 769: 724: 688: 652: 591: 571:, pre-existing CNS lesions, or CNS inflammation, or who have had a 556: 521: 505: 485: 171: 163:, as well as in animal husbandry, specifically poultry production. 5126: 3859: 5546: 3862:"Antimicrobial drug prescribing for pneumonia in ambulatory care" 2878: 1342: 707: 257: 4486:"Activities of Quinolones Against Obligately Anaerobic Bacteria" 4008: 3860:

MacDougall C, Guglielmo BJ, Maselli J, Gonzales R (March 2005).

3734:"Activities of Quinolones Against Obligately Anaerobic Bacteria" 3545: 3281: 2496:

Babar SM (October 2013). "SIADH associated with ciprofloxacin".

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atom in their chemical structure and are effective against both

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Shehab N, Patel PR, Srinivasan A, Budnitz DS (September 2008).

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Events that may occur in acute overdose are rare, and include

3377: 2170:"Do fluoroquinolones commonly cause arthropathy in children?" 2118: 1793: 4997:"Consolidated list of products – Pharmaceuticals 12th issue" 3138: 3018: 2740: 2460: 1694:, and several agents have veterinary-specific applications. 1430: 3964: 2666:

Newton ER, Akerman AW, Strassle PD, Kibbe MR (March 2021).

1424: 825: 808: 727: 594: 5136:"Family Practice Notebook" entry page for Fluoroquinolones 4448: 4398: 4326: 3924:

Nelson JM, Chiller TM, Powers JH, Angulo FJ (April 2007).

3518: 2665: 2018:

American Journal of Respiratory and Critical Care Medicine

5984: 5960: 4532: 3923: 3487:"Fluoroquinolones Antibiotic Alert – especially with EDS" 1883: 746: 3580: 3059: 2365: 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

4777: 4575: 4413: 3519:

Nardiello S, Pizzella T, Ariviello R (March 2002). "".

5024:

Clinical Ophthalmology: Contemporary Perspectives, 9/e

4635:"FDA updates warnings for fluoroquinolone antibiotics" 4088: 2787:"Data Mining Analysis of Multiple Antibiotics in AERS" 730:

attached to the central ring system, typically at the

3667: 2075: 1764:

United States Department of Health and Human Services

186:, one of the most widely used antibiotics worldwide. 4053: 3179: 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

4282: 4189: 4143:"Emerging mechanisms of fluoroquinolone resistance" 2407: 2405: 4971:Seminars in Respiratory and Critical Care Medicine 3405: 3403: 3401: 3095: 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: 2317: 2153:: CS1 maint: DOI inactive as of September 2024 ( 2065:. Food and Drug Administration. 18 November 2008. 1842: 741:active against eukaryotic type II topoisomerase. 6099: 4906: 4904: 4902: 4900: 4898: 4896: 4894: 4892: 4890: 4888: 4856: 4483: 3731: 3288:. New York: McGraw-Hill, Medical Pub. Division. 2965: 2402: 1932: 256:children are severely restricted. Only inhalant 4964: 4616:. San Diego: Academic Press Inc. pp. 1–22. 3398: 2961: 2959: 2957: 2308: 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). 3688: 3618: 3206: 2784: 2352: 2208: 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: 4914: 4885: 4611: 4283:Elsea SH, Osheroff N, Nitiss JL (July 1992). 2802: 2573: 2167: 1979: 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 4809: 4629: 4627: 4625: 4623: 4526: 4493:Anti-Infective Agents in Medicinal Chemistry 3786:Bioorganic & Medicinal Chemistry Letters 3779: 3777: 3741:Anti-Infective Agents in Medicinal Chemistry 3371: 3302: 2954: 2887: 2850:International Journal of Infectious Diseases 2567: 1328: 166:Nearly all quinolone antibiotics in use are 4960: 4958: 4956: 4954: 4752:"FDA Panel Seeks Tougher Antibiotic Labels" 4645: 4322: 4320: 4244:"The quinolones: past, present, and future" 4082: 609:Antibiotic misuse and bacterial resistances 5168: 5154: 4136: 4134: 3783: 3250:"Antibiotics Tied to Heart Valve Problems" 3200: 2785:Levine JG, Szarfman A (15 December 2006). 2616: 938: 881: 674:Agency for Healthcare Research and Quality 49: 5014: 4857:Lilley SH, Malone R, King DE (May 2000). 4833: 4822:The Journal of Antimicrobial Chemotherapy 4653:"Fluoroquinolone Safety Labeling Changes" 4620: 4360: 4300: 4259: 4237: 4235: 4215: 4166: 4114: 4026: 3941: 3885: 3836: 3774: 3624: 3574: 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: 2411: 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). 4951: 4783:"NegGram® Caplets (nalidixic acid, USP)" 4596: 4484:Schaumann R, Rodloff AC (January 2007). 4377: 4317: 4241: 3732:Schaumann R, Rodloff AC (January 2007). 3584:The Pediatric Infectious Disease Journal 3275: 2539:Rouveix B (November–December 2006). "". 2532: 2078:The Pediatric Infectious Disease Journal 1778: 1429: 1417: 1341: 928: 706: 463: 203: 193: 5057:"Drug Company Taking Tequin Off Market" 4915:Oliphant CM, Green GM (February 2002). 4581:"NegGram Caplets (nalidixic acid, USP)" 4183: 4131: 3673:"Highlights of Prescribing Information" 3452: 3351: 3308: 3247: 2708: 2538: 2265: 2209:Bradley JS, Jackson MA (October 2011). 2168:Forsythe CT, Ernst ME (November 2007). 1973: 1346:Nalidixic acid. Although technically a 838: 230:being at increased risk for developing 14: 6100: 5769: 5655: 5054: 4939:from the original on 29 September 2007 4749: 4383: 4232: 4140: 3908: 2775: 1877: 1843:Andersson MI, MacGowan AP (May 2003). 1707:– 2nd/3rd gen, related to temafloxacin 1439:group, the R substituent in blue is a 702: 5721: 5598: 5149: 5020: 4095:Antimicrobial Agents and Chemotherapy 2495: 2489: 1800:Antimicrobial Agents and Chemotherapy 432:Fluoroquinolones prolong the heart's 100: 4917:"Quinolones: a comprehensive review" 4815: 4614:The quinolones: history and overview 3958: 3409: 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 1619: 1511: 550: 345: 333:. The cause is not well understood. 5841: 4967:"Clinical Usefulness of Quinolones" 4743: 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 1568: 1470: 1354:Although not formally a quinolone, 814: 24: 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 756: 734:. Most of them are named with the 293: 25: 6119: 5122:U.S. Food and Drug Administration 5100:to help reach a consensus. › 5079: 5027:. 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Food and Drug Administration. 3661: 3539: 3512: 3493: 3479: 3446: 3345: 3248:Bakalar N (17 September 2019). 3241: 3173: 3132: 3089: 3053: 3012: 2994: 2922: 2837: 2796: 2734: 2659: 2610: 2454: 2283: 2243: 2202: 2161: 2133:10.1590/S0325-00752010000600008 2112: 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: 795: 475: 189: 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). 2069: 2052: 2008: 1926: 1836: 1787: 1772: 1402: 901:Tooltip Volume of distribution 13: 1: 5511:Trimethoprim/sulfamethoxazole 5085: 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 1741: 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 7: 5516:Ormetoprim/sulfadimethoxine 3453:Ford C, Law F (July 2014). 2968:Current Medicinal Chemistry 250: 10: 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 1337: 1323:= Dosage applies only to C 1322: 943:Tooltip Hepatic impairment 889:Tooltip Terminal half-life 732:6-position or C-8 position 612: 362: 323: 6058: 6036: 5993: 5983: 5946: 5918: 5897: 5840: 5768: 5720: 5654: 5645: 5597: 5569: 5534: 5526:Pyrimethamine/sulfadoxine 5503: 5453: 5390: 5362: 5283: 5268: 5218: 5196: 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: 127: 113: 108: 94: 89: 77: 69: 64: 48: 39: 34: 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 381: 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 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: 5990: 5958: 5957: 5693:Levonadifloxacin 5652: 5651: 5647:Fluoroquinolones 5595: 5594: 5400:Sulfadimethoxine 5372:Sulfamethoxazole 5293:Sulfaisodimidine 5281: 5280: 5216: 5215: 5170: 5163: 5156: 5147: 5146: 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: 818: 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: 31: 21: 18:Fluoroquinolones 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: 5053: 5049: 5039: 5037: 5035: 5019: 5015: 5005: 5003: 4999: 4995: 4994: 4990: 4980: 4978: 4963: 4952: 4942: 4940: 4913: 4886: 4876: 4874: 4855: 4851: 4814: 4810: 4805: 4801: 4791: 4789: 4785: 4776: 4772: 4762: 4760: 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: 4610: 4606: 4595: 4591: 4583: 4574: 4570: 4531: 4527: 4517: 4515: 4511: 4488: 4482: 4478: 4447: 4443: 4412: 4408: 4397: 4393: 4382: 4378: 4325: 4318: 4281: 4277: 4240: 4233: 4188: 4184: 4139: 4132: 4087: 4083: 4062:(10): 629–640. 4052: 4048: 4007: 4003: 3998: 3994: 3963: 3959: 3922: 3918: 3907: 3903: 3858: 3854: 3809: 3805: 3782: 3775: 3765: 3763: 3762:on 16 June 2010 3759: 3736: 3730: 3726: 3687: 3683: 3675: 3666: 3662: 3623: 3619: 3590:(10): 879–891. 3579: 3575: 3544: 3540: 3517: 3513: 3508:Wayback Machine 3498: 3494: 3485: 3484: 3480: 3470: 3468: 3464: 3457: 3451: 3447: 3412:Pharmacotherapy 3408: 3399: 3376: 3372: 3362: 3360: 3356: 3350: 3346: 3307: 3303: 3296: 3280: 3276: 3266: 3264: 3246: 3242: 3205: 3201: 3178: 3174: 3137: 3133: 3094: 3090: 3058: 3054: 3017: 3013: 3000: 2999: 2995: 2964: 2955: 2945: 2943: 2928: 2927: 2923: 2886: 2879: 2842: 2838: 2801: 2797: 2789: 2783: 2776: 2739: 2735: 2725: 2723: 2714: 2713: 2709: 2664: 2660: 2615: 2611: 2572: 2568: 2537: 2533: 2494: 2490: 2459: 2455: 2410: 2403: 2364: 2353: 2316: 2309: 2299: 2297: 2289: 2288: 2284: 2271: 2270: 2266: 2256: 2254: 2249: 2248: 2244: 2207: 2203: 2166: 2162: 2146: 2145: 2117: 2113: 2074: 2070: 2062: 2058: 2057: 2053: 2013: 2009: 1978: 1974: 1945:(10): 957–965. 1931: 1927: 1882: 1878: 1841: 1837: 1792: 1788: 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: 6111: 6110: 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 5173: 5172: 5165: 5158: 5150: 5144: 5143: 5137: 5124: 5115: 5109: 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: 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: 5062: 5058: 5051: 5036: 5030: 5026: 5025: 5017: 4998: 4992: 4976: 4972: 4968: 4961: 4959: 4957: 4955: 4938: 4934: 4930: 4926: 4922: 4918: 4911: 4909: 4907: 4905: 4903: 4901: 4899: 4897: 4895: 4893: 4891: 4889: 4872: 4868: 4864: 4860: 4853: 4845: 4841: 4836: 4831: 4827: 4823: 4819: 4812: 4803: 4784: 4780: 4774: 4759: 4758: 4753: 4746: 4735: 4728: 4722: 4711: 4704: 4698: 4682: 4678: 4672: 4661: 4654: 4648: 4640: 4636: 4630: 4628: 4626: 4624: 4615: 4608: 4600: 4593: 4582: 4578: 4572: 4564: 4560: 4556: 4552: 4548: 4544: 4540: 4536: 4529: 4510: 4506: 4502: 4498: 4494: 4487: 4480: 4472: 4468: 4464: 4460: 4456: 4452: 4445: 4437: 4433: 4429: 4425: 4421: 4417: 4410: 4402: 4395: 4387: 4380: 4372: 4368: 4363: 4358: 4354: 4350: 4346: 4342: 4338: 4334: 4330: 4323: 4321: 4312: 4308: 4303: 4298: 4294: 4290: 4286: 4279: 4271: 4267: 4262: 4257: 4253: 4249: 4245: 4238: 4236: 4227: 4223: 4218: 4213: 4209: 4205: 4201: 4197: 4193: 4186: 4178: 4174: 4169: 4164: 4160: 4156: 4152: 4148: 4144: 4137: 4135: 4126: 4122: 4117: 4112: 4108: 4104: 4100: 4096: 4092: 4085: 4077: 4073: 4069: 4065: 4061: 4057: 4050: 4043: 4038: 4034: 4029: 4024: 4020: 4016: 4012: 4005: 3996: 3988: 3984: 3980: 3976: 3972: 3968: 3961: 3953: 3949: 3944: 3939: 3935: 3931: 3927: 3920: 3912: 3905: 3897: 3893: 3888: 3883: 3879: 3875: 3871: 3867: 3863: 3856: 3848: 3844: 3839: 3834: 3830: 3826: 3822: 3818: 3814: 3807: 3799: 3795: 3791: 3787: 3780: 3778: 3758: 3754: 3750: 3746: 3742: 3735: 3728: 3720: 3716: 3712: 3708: 3704: 3700: 3696: 3692: 3685: 3674: 3670: 3664: 3656: 3652: 3648: 3644: 3640: 3636: 3632: 3628: 3621: 3613: 3609: 3605: 3601: 3597: 3593: 3589: 3585: 3577: 3569: 3565: 3561: 3557: 3553: 3549: 3542: 3534: 3530: 3526: 3522: 3515: 3509: 3505: 3501: 3500:2011 Document 3496: 3488: 3482: 3463: 3456: 3449: 3441: 3437: 3433: 3429: 3425: 3421: 3417: 3413: 3406: 3404: 3402: 3393: 3389: 3385: 3382:(in French). 3381: 3374: 3355: 3348: 3340: 3336: 3332: 3328: 3324: 3320: 3316: 3312: 3305: 3297: 3291: 3287: 3286: 3278: 3263: 3259: 3255: 3251: 3244: 3236: 3232: 3227: 3222: 3218: 3214: 3210: 3203: 3195: 3191: 3187: 3183: 3176: 3168: 3164: 3159: 3154: 3150: 3146: 3142: 3135: 3127: 3123: 3119: 3115: 3111: 3107: 3103: 3099: 3092: 3084: 3080: 3076: 3072: 3068: 3064: 3056: 3048: 3044: 3039: 3034: 3030: 3026: 3022: 3015: 3007: 3003: 2997: 2989: 2985: 2981: 2977: 2973: 2969: 2962: 2960: 2958: 2941: 2937: 2936: 2931: 2925: 2917: 2913: 2908: 2903: 2899: 2895: 2891: 2884: 2882: 2873: 2869: 2864: 2859: 2855: 2851: 2847: 2840: 2832: 2828: 2823: 2818: 2814: 2810: 2806: 2799: 2788: 2781: 2779: 2770: 2766: 2761: 2756: 2752: 2748: 2744: 2737: 2721: 2717: 2711: 2703: 2699: 2694: 2689: 2685: 2681: 2677: 2673: 2669: 2662: 2654: 2650: 2645: 2640: 2636: 2632: 2629:(7084): 869. 2628: 2624: 2620: 2613: 2605: 2601: 2597: 2593: 2589: 2585: 2581: 2577: 2570: 2562: 2558: 2554: 2550: 2546: 2542: 2535: 2527: 2523: 2519: 2515: 2511: 2507: 2503: 2499: 2492: 2484: 2480: 2476: 2472: 2468: 2464: 2457: 2449: 2445: 2440: 2435: 2431: 2427: 2423: 2419: 2415: 2408: 2406: 2397: 2393: 2389: 2385: 2381: 2377: 2373: 2369: 2362: 2360: 2358: 2356: 2347: 2343: 2338: 2333: 2329: 2325: 2321: 2314: 2312: 2296: 2292: 2286: 2278: 2274: 2268: 2252: 2246: 2238: 2234: 2229: 2224: 2220: 2216: 2212: 2205: 2197: 2193: 2188: 2183: 2179: 2175: 2171: 2164: 2156: 2150: 2142: 2138: 2134: 2130: 2126: 2122: 2115: 2107: 2103: 2099: 2095: 2091: 2087: 2083: 2079: 2072: 2061: 2055: 2047: 2043: 2039: 2035: 2031: 2027: 2023: 2019: 2011: 2003: 1999: 1995: 1991: 1987: 1983: 1976: 1968: 1964: 1960: 1956: 1952: 1948: 1944: 1940: 1936: 1929: 1921: 1917: 1912: 1907: 1903: 1899: 1895: 1891: 1887: 1880: 1872: 1868: 1863: 1858: 1854: 1850: 1846: 1839: 1831: 1827: 1822: 1817: 1813: 1809: 1805: 1801: 1797: 1790: 1782: 1775: 1771: 1768: 1765: 1761: 1760: 1754: 1736: 1733: 1730: 1727: 1724: 1723:marbofloxacin 1721: 1718: 1715: 1712: 1709: 1706: 1703: 1700: 1697: 1696: 1695: 1693: 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: 1617: 1615: 1608: 1605: 1603: 1600: 1598: 1595: 1593: 1590: 1588: 1587:grepafloxacin 1585: 1583: 1580: 1579: 1578: 1576: 1566: 1564: 1557: 1554: 1552: 1549: 1547: 1544: 1542: 1539: 1537: 1534: 1532: 1529: 1527: 1524: 1522: 1521:ciprofloxacin 1519: 1518: 1517: 1509: 1508: 1504: 1500: 1496: 1489: 1486: 1484: 1483:oxolinic acid 1481: 1478: 1475: 1474: 1468: 1466: 1462: 1461:ciprofloxacin 1458: 1453: 1451: 1442: 1438: 1432: 1428: 1426: 1423: 1419: 1415: 1411: 1400: 1396: 1392: 1388: 1386: 1382: 1381:oxolinic acid 1378: 1374: 1369: 1365: 1361: 1357: 1349: 1348:naphthyridine 1344: 1321: 1315: 1310: 1305: 1300: 1295: 1290: 1285: 1280: 1275: 1270: 1265: 1263: 1260: 1259: 1249: 1244: 1239: 1234: 1229: 1224: 1219: 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