Quinolone antibiotic

564:. 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 184: 1384:

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.

194: 40: 1332: 697: 1420: 2919:"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)]" 1737: 266:

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

712:, 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 318:

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

1423:

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

536:, 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. 3049:

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".

4641: 348:, 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. 339:

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

793:, 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 627:

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

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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

4715: 4691: 2004:

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

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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

586:

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

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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.

1441:

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.

435:, but in practice, this appears relatively uncommon in part because the most widely prescribed fluoroquinolones (ciprofloxacin and levofloxacin) only minimally prolong the QT interval. 2262:"FDA Drug Safety Communication: FDA advises restricting fluoroquinolone antibiotic use for certain uncomplicated infections; warns about disabling side effects that can occur together" 4648: 2918: 477:, and products containing calcium, iron, or zinc invariably result in marked reduction of oral absorption of fluoroquinolones. Other drugs that interact with fluoroquinolones include 4666:"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)" 1405:. Naphthyridone and quinolone classes of antibiotics prevent bacterial DNA replication by inhibition of DNA unwinding events, and can be both bacteriostatic and bacteriocidal. (See 5086: 4522:

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".

5514: 4722: 4698: 2280:"Safety Alerts for Human Medical Products – Fluoroquinolone Antibiotics: FDA Requires Labeling Changes Due to Low Blood Sugar Levels and Mental Health Side Effects" 3492: 5509: 4692:"FDA Briefing Document Joint Meeting of the Antimicrobial Drugs Advisory Committee and the Drug Safety and Risk Management Advisory Committee, November 5, 2015" 2309:"Impact of the US Food and Drug Administration warning regarding increased risk of aortic aneurysms or aortic dissections on fluoroquinolone prescribing trends" 1923: 672:

pumps can act to decrease intracellular quinolone concentration. In gram-negative bacteria, plasmid-mediated resistance genes produce proteins that can bind to

5310: 5128: 4669: 4274:"Cytotoxicity of quinolones toward eukaryotic cells. Identification of topoisomerase II as the primary cellular target for the quinolone CP-115,953 in yeast" 2143: 1752: 457:

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

67: 1364:

have been synthesized, but only a handful have found their way into clinical practice. The first generation also included other quinolone drugs, such as

4716:"Transcript: Joint Meeting of the Antimicrobial Drugs Advisory Committee and the Drug Safety and Risk Management Advisory Committee, November 5, 2015" 257:

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

5156: 3238: 4839: 665:. In addition, they are commonly prescribed for medical conditions, such as acute respiratory illness, that are usually caused by viral infections. 4740: 4403:

Castora FJ, Vissering FF, Simpson MV (September 1983). "The effect of bacterial DNA gyrase inhibitors on DNA synthesis in mammalian mitochondria".

3802:"Infectious Diseases Society of America/American Thoracic Society consensus guidelines on the management of community-acquired pneumonia in adults" 5049: 2990: 449:

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

5459: 1785:"Isolation and molecular characterization of nalidixic acid-resistant extraintestinal pathogenic Escherichia coli from retail chicken products" 439: 5106: 2928: 3915:"Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story" 3954:

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".

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Farinas ER, et al. (Public Health Service Food and Drug Administration Center for Drug Evaluation and Research) (1 March 2005).

773:. For many Gram-negative bacteria, DNA gyrase is the target, whereas topoisomerase IV is the target for many Gram-positive bacteria. 2705:"FDA warns about increased risk of ruptures or tears in the aorta blood vessel with fluoroquinolone antibiotics in certain patients" 3661: 3475: 2991:"Disabling and potentially permanent side effects lead to suspension or restrictions of quinolone and fluoroquinolone antibiotics" 3773:

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

857: 4388:

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

532:

symptoms due to quinolones displacing benzodiazepines from their binding sites. Fluoroquinolones have varying specificity for

6052: 5149: 5021: 3282: 1613:

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

5263: 1969:

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

44:

The second generation fluoroquinolone, ciprofloxacin. The two ringed nitrogen containing system with a ketone is called a

3444:"Guidance for the use and reduction of misuse of benzodiazepines and other hypnotics and anxiolytics in general practice" 2403:"Fluoroquinolones and tendinopathy: a guide for athletes and sports clinicians and a systematic review of the literature" 2355:

Stephenson AL, Wu W, Cortes D, Rochon PA (September 2013). "Tendon Injury and Fluoroquinolone Use: A Systematic Review".

2048: 4847: 3298:

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

650:, commonly exhibit resistance. Widespread veterinary usage of quinolones, in particular in Europe, has been implicated. 4925: 3488: 5208: 5110: 4043:

Robicsek A, Jacoby GA, Hooper DC (October 2006). "The worldwide emergence of plasmid-mediated quinolone resistance".

4000:"Antibiotic resistance among gram-negative bacilli in US intensive care units: implications for fluoroquinolone use" 3342: 6069: 5352: 5142: 613: 4848:"New Classification and Update on the Quinolone Antibiotics – May 1, 2000 – American Academy of Family Physicians" 2955:

De Sarro A, De Sarro G (March 2001). "Adverse reactions to fluoroquinolones. an overview on mechanistic aspects".

2794:"Antibiotics and hospital-acquired Clostridium difficile infection: update of systematic review and meta-analysis" 2775: 708:

by preventing bacterial DNA from unwinding and duplicating. Specifically, they inhibit the ligase activity of the

229:, fluoroquinolones are the "drugs of choice" due to their ability to enter bone tissue without chelating it, as 6096: 724: 5941: 461:

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

5499: 5118: 4771: 4569: 356: 5273: 2835:"Risk factors for development of Clostridium difficile infection due to BI/NAP1/027 strain: a meta-analysis" 5988: 5380: 5100: 4623: 4080:"NorM, a putative multidrug efflux protein, of Vibrio parahaemolyticus and its homolog in Escherichia coli" 3010:"Macrolides vs. quinolones for community-acquired pneumonia: meta-analysis of randomized controlled trials" 2923: 1746: 276: 236:

Fluoroquinolones are featured prominently in guidelines for the treatment of hospital-acquired pneumonia.

287:

While typical drug side effects reactions are mild to moderate, sometimes serious adverse effects occur.

279:, or when alternative treatment options require parenteral administration and oral therapy is preferred. 5134: 5091: 1376:, which were introduced in the 1970s. They proved to be only marginal improvements over nalidixic acid. 904: 739: 212:

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

529: 525: 134: 1320:. The other parameters an average of the values available in the literature irrespective of dosage. 738:

could be bactericidal. Bacterial cytotoxicity could arise from incomplete repair of closely spaced

5504: 2239: 1348: 630: 103: 3800:

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

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

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

5336: 5332: 5216: 3657: 2137: 769: 720: 709: 669: 661:, and acute upper respiratory tract infection, according to a study supported in part by the 637: 607: 3450: 700:

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

4586:

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

4329: 4318:"Oxidation of the guanine nucleotide pool underlies cell death by bactericidal antibiotics" 2657:"Association of Fluoroquinolone Use With Short-term Risk of Development of Aortic Aneurysm" 549: 442:

it was discovered that fluoroquinolones could increase the risk for heart valve diseases.

425:

by blocking voltage-gated potassium channels. Prolongation of the QT interval can lead to

8: 5685: 847: 837: 819: 432: 427: 216: 4333: 3678:

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

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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.

5936: 5408: 4823: 4806: 4547: 4350: 4317: 4205: 4180: 4156: 4131: 3875: 3850: 3826: 3801: 3703: 3639: 3627: 3596: 3424: 3323: 3110: 2732:"Community-associated Clostridium difficile infection and antibiotics: a meta-analysis" 2681: 2656: 2632: 2607: 2588: 2510: 2427: 2402: 2380: 2090: 2030: 1899: 1874: 1339:, it is considered the predecessor of all subsequently developed quinolone antibiotics. 926: 869: 4590:. Vol. XIII–XIV (2nd ed.). Washington DC: American Society for Microbiology. 4290: 4273: 4104: 4079: 4078:

Morita Y, Kodama K, Shiota S, Mine T, Kataoka A, Mizushima T, Tsuchiya T (July 1998).

4056: 3998:

Neuhauser MM, Weinstein RA, Rydman R, Danziger LH, Karam G, Quinn JP (February 2003).

3786: 2833:

Vardakas KZ, Konstantelias AA, Loizidis G, Rafailidis PI, Falagas ME (November 2012).

2308: 2049:"Adverse Event Review: Levaquin® (levofloxacin): Pediatric Advisory Committee Meeting" 1809: 1784: 5192: 5017: 4917: 4828: 4539: 4535: 4455: 4420: 4416: 4355: 4295: 4254: 4210: 4161: 4109: 4060: 4021: 3971: 3936: 3880: 3831: 3695: 3631: 3588: 3552: 3517: 3416: 3376: 3367:

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

3315: 3278: 3246: 3219: 3178: 3151: 3102: 3098: 3067: 3031: 3026: 3009: 2972: 2900: 2856: 2815: 2753: 2704: 2686: 2637: 2580: 2545: 2502: 2467: 2432: 2372: 2330: 2261: 2221: 2180: 2125: 2082: 2022: 1986: 1951: 1943: 1904: 1890: 1855: 1814: 1653:

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

1361: 778: 603: 378: 296: 141: 4551: 3707: 3643: 3600: 3428: 3327: 3114: 2592: 2514: 2384: 2121: 2094: 2034: 1800: 1482:

Structurally related first-generation drugs, but formally not 4-quinolones, include

1351:(UTIs) in humans. Nalidixic acid was discovered by George Lesher and coworkers in a 309:

syndrome, atherosclerosis, peripheral vascular disease, and a history of aneurysms.

5681: 5388: 5360: 4818: 4531: 4489: 4447: 4412: 4345: 4337: 4285: 4244: 4200: 4192: 4151: 4143: 4099: 4091: 4052: 4011: 3963: 3926: 3870: 3862: 3821: 3813: 3782: 3737: 3687: 3623: 3580: 3544: 3408: 3307: 3209: 3141: 3094: 3059: 3021: 2964: 2890: 2846: 2805: 2743: 2676: 2668: 2627: 2619: 2572: 2537: 2494: 2459: 2422: 2414: 2364: 2320: 2211: 2170: 2117: 2074: 2014: 1978: 1935: 1894: 1886: 1845: 1804: 1796: 1680: 1347:

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

916: 685: 654: 646: 565: 498: 90: 3412: 3343:"Consult: One-Year Post Pediatric Exclusivity Postmarketing Adverse Events Review" 1924:"Should Physicians Consider the Environmental Effects of Prescribing Antibiotics?" 1550:

A structurally related second-generation drug, but formally not a 4-quinolone, is

1505:

The second-generation class is sometimes subdivided into "Class 1" and "Class 2".

5577: 5403: 5122: 5081: 3967: 3584: 3548: 3496: 3399:

Fish DN (October 2001). "Fluoroquinolone adverse effects and drug interactions".

2541: 2078: 1982: 1601:

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

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

4955: 4767: 4565: 4493: 3741: 2851: 2834: 2672: 2463: 2108:

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).

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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

6090: 5918: 5868: 5858: 5816: 5806: 5796: 5728: 5652: 5610: 5530: 5454: 5423: 5342: 5328: 5316: 5306: 5300: 5296: 5291: 5281: 5236: 5107:

Information for Healthcare Professionals: Fluoroquinolone Antimicrobial Drugs

5076: 4859: 3311: 3250: 2968: 2623: 2498: 1947: 1711: 1658: 1637: 1617: 1575: 1509: 1471: 1449: 1369: 1336: 938: 790: 755: 587: 572: 395: 383: 230: 220: 197: 172: 168: 164: 137: 72: 4905: 4341: 5873: 5863: 5848: 5838: 5811: 5791: 5786: 5781: 5776: 5771: 5766: 5748: 5743: 5738: 5733: 5723: 5718: 5677: 5672: 5474: 5365: 5246: 5131:"Antibacterial Agents; Structure Activity Relationships," André Bryskier MD 4921: 4832: 4543: 4359: 4258: 4214: 4165: 4147: 4064: 4025: 4016: 3999: 3975: 3940: 3884: 3866: 3835: 3699: 3635: 3592: 3556: 3521: 3420: 3380: 3319: 3223: 3214: 3197: 3182: 3155: 3106: 3071: 3035: 2976: 2904: 2860: 2819: 2757: 2690: 2584: 2549: 2506: 2471: 2436: 2376: 2334: 2225: 2216: 2199: 2184: 2129: 2086: 2026: 1990: 1955: 1908: 1859: 1818: 1723: 1717: 1699: 1687: 1654: 1647: 1642: 1632: 1627: 1622: 1602: 1595: 1590: 1585: 1580: 1570: 1563: 1524: 1519: 1453: 1445: 1432:

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

1250: 1184: 1122: 1082: 658: 514: 506: 490: 258: 187: 4459: 4424: 4299: 4113: 4095: 2641: 1416:

to the all-carbon containing ring, typically at the C-6 or C-8 positions.

1401:

during an attempt at synthesis of the chloroquinoline antimalarial agent,

122: 6034: 6026: 6006: 5959: 5893: 5853: 5801: 5690: 5540: 5479: 5433: 5393: 5370: 5241: 5221: 5165: 5164: 2810: 2793: 2748: 2731: 1850: 1833: 1705: 1529: 1425: 1402: 1356: 1000: 557: 518: 422: 411: 407: 262: 250: 209: 145: 4451: 3614:

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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

183: 5996: 5922: 5909: 5898: 5843: 5700: 5695: 5667: 5600: 5570: 5418: 5231: 5186: 3063: 2832: 1693: 1668: 1544: 1539: 1514: 1465: 1429: 1398: 1352: 681: 673: 486: 482: 478: 415: 403: 225: 30: 4196: 3130:"Emergency department visits for antibiotic-associated adverse events" 2576: 575:, or active structure, of the fluoroquinolone class is based upon the 6016: 6011: 6001: 5983: 5657: 5625: 5595: 5545: 5398: 5321: 4316:

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

3900:

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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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European Journal of Obstetrics, Gynecology, and Reproductive Biology

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

4249: 4232: 3931: 3914: 3817: 3146: 3129: 2895: 2878: 1551: 1438: 1410: 794: 758: 713: 677: 641: 580: 560:, pre-existing CNS lesions, or CNS inflammation, or who have had a 545: 510: 494: 474: 160: 152:, as well as in animal husbandry, specifically poultry production. 5115: 3848: 5535: 3851:"Antimicrobial drug prescribing for pneumonia in ambulatory care" 2867: 1331: 696: 246: 4475:"Activities of Quinolones Against Obligately Anaerobic Bacteria" 3997: 3849:

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

3723:"Activities of Quinolones Against Obligately Anaerobic Bacteria" 3534: 3270: 2485:

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

193: 163:

atom in their chemical structure and are effective against both

39: 5095: 4373:

Bergan T (1988). "Pharmacokinetics of fluorinated quinolones".

3799: 3128:

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

858: 561: 470: 4807:"Quinolone generations: natural history or natural selection?" 597: 445:

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

3366: 2159:"Do fluoroquinolones commonly cause arthropathy in children?" 2107: 1782: 4986:"Consolidated list of products – Pharmaceuticals 12th issue" 3127: 3007: 2729: 2449: 1683:, and several agents have veterinary-specific applications. 1419: 3953: 2655:

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

1413: 814: 797: 716: 583: 5125:"Family Practice Notebook" entry page for Fluoroquinolones 4437: 4387: 4315: 3913:

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

3507: 2654: 2007:

American Journal of Respiratory and Critical Care Medicine

5973: 5949: 4521: 3912: 3476:"Fluoroquinolones Antibiotic Alert – especially with EDS" 1872: 735: 3569: 3048: 2354: 676:, protecting it from the action of quinolones. Finally, 668:

Three mechanisms of resistance are known. Some types of

623:

or doxycycline as first-line agents. The Drug-Resistant

4766: 4564: 4402: 3508:

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

5013:

Clinical Ophthalmology: Contemporary Perspectives, 9/e

4624:"FDA updates warnings for fluoroquinolone antibiotics" 4077: 2776:"Data Mining Analysis of Multiple Antibiotics in AERS" 719:

attached to the central ring system, typically at the

3656: 2064: 1753:

United States Department of Health and Human Services

175:, one of the most widely used antibiotics worldwide. 4042: 3168: 2307:

Rizk JG, Slejko JF, Heil EL, Seo D, Qato DM (2024).

1748:

FDA updates warnings for fluoroquinolone antibiotics

16:

Class of antibacterial drugs, subgroup of quinolones

4271: 4178: 4132:"Emerging mechanisms of fluoroquinolone resistance" 2396: 2394: 4960:Seminars in Respiratory and Critical Care Medicine 3394: 3392: 3390: 3084: 2302: 2300: 2240:"FDA orders 'black box' label on some antibiotics" 2200:"The use of systemic and topical fluoroquinolones" 4899: 4897: 4392:. Hong Kong: Sieber and McIntyre. pp. 23–36. 2879:"Antimicrobial safety: focus on fluoroquinolones" 2350: 2348: 2346: 2344: 2306: 2142:: CS1 maint: DOI inactive as of September 2024 ( 2054:. Food and Drug Administration. 18 November 2008. 1831: 730:active against eukaryotic type II topoisomerase. 6088: 4895: 4893: 4891: 4889: 4887: 4885: 4883: 4881: 4879: 4877: 4845: 4472: 3720: 3277:. New York: McGraw-Hill, Medical Pub. Division. 2954: 2391: 1921: 245:children are severely restricted. Only inhalant 4953: 4605:. San Diego: Academic Press Inc. pp. 1–22. 3387: 2950: 2948: 2946: 2297: 1922:Balch J, Schoen JH, Patel PK (1 October 2017). 863:Tooltip Area under the curve (pharmacokinetics) 750:Fluoroquinolones can enter in cells easily via 4668:. Food and Drug Administration. Archived from 4181:"Mechanism of quinolone action and resistance" 4179:Aldred KJ, Kerns RJ, Osheroff N (March 2014). 3677: 3607: 3195: 2773: 2341: 2197: 1875:"Quinolones: from antibiotics to autoinducers" 885: 742:in the DNA resulting in double-strand breaks. 544:Quinolones are not recommended in people with 402:, but less frequently than those treated with 5150: 4903: 4874: 4600: 4272:Elsea SH, Osheroff N, Nitiss JL (July 1992). 2791: 2562: 2156: 1968: 1940:10.1001/journalofethics.2017.19.10.peer1-1710 524:Administration of quinolone antibiotics to a 473:, such as aluminium- or magnesium-containing 440:Journal of the American College of Cardiology 4798: 4618: 4616: 4614: 4612: 4515: 4482:Anti-Infective Agents in Medicinal Chemistry 3775:Bioorganic & Medicinal Chemistry Letters 3768: 3766: 3730:Anti-Infective Agents in Medicinal Chemistry 3360: 3291: 2943: 2876: 2839:International Journal of Infectious Diseases 2556: 1317: 155:Nearly all quinolone antibiotics in use are 4949: 4947: 4945: 4943: 4741:"FDA Panel Seeks Tougher Antibiotic Labels" 4634: 4311: 4309: 4233:"The quinolones: past, present, and future" 4071: 598:Antibiotic misuse and bacterial resistances 5157: 5143: 4125: 4123: 3772: 3239:"Antibiotics Tied to Heart Valve Problems" 3189: 2774:Levine JG, Szarfman A (15 December 2006). 2605: 927: 870: 663:Agency for Healthcare Research and Quality 38: 5003: 4846:Lilley SH, Malone R, King DE (May 2000). 4822: 4811:The Journal of Antimicrobial Chemotherapy 4642:"Fluoroquinolone Safety Labeling Changes" 4609: 4349: 4289: 4248: 4226: 4224: 4204: 4155: 4103: 4015: 3930: 3874: 3825: 3763: 3613: 3563: 3213: 3202:The Journal of Antimicrobial Chemotherapy 3145: 3025: 2894: 2850: 2809: 2798:The Journal of Antimicrobial Chemotherapy 2769: 2767: 2747: 2736:The Journal of Antimicrobial Chemotherapy 2680: 2631: 2426: 2400: 2324: 2215: 2174: 1898: 1849: 1838:The Journal of Antimicrobial Chemotherapy 1808: 1702:– 2nd gen, metabolizes into ciprofloxacin 5085:) is being considered for deletion. See 4954:Ambrose PG, Owens Jr RC (1 March 2000). 4940: 4772:"NegGram® Caplets (nalidixic acid, USP)" 4585: 4473:Schaumann R, Rodloff AC (January 2007). 4366: 4306: 4230: 3721:Schaumann R, Rodloff AC (January 2007). 3573:The Pediatric Infectious Disease Journal 3264: 2528:Rouveix B (November–December 2006). "". 2521: 2067:The Pediatric Infectious Disease Journal 1767: 1418: 1406: 1330: 917: 695: 452: 192: 182: 5046:"Drug Company Taking Tequin Off Market" 4904:Oliphant CM, Green GM (February 2002). 4570:"NegGram Caplets (nalidixic acid, USP)" 4172: 4120: 3662:"Highlights of Prescribing Information" 3441: 3340: 3297: 3236: 2697: 2527: 2254: 2198:Bradley JS, Jackson MA (October 2011). 2157:Forsythe CT, Ernst ME (November 2007). 1962: 1335:Nalidixic acid. Although technically a 827: 219:being at increased risk for developing 6089: 5758: 5644: 5043: 4928:from the original on 29 September 2007 4738: 4372: 4221: 4129: 3897: 2764: 1866: 1832:Andersson MI, MacGowan AP (May 2003). 1696:– 2nd/3rd gen, related to temafloxacin 1428:group, the R substituent in blue is a 691: 5710: 5587: 5138: 5009: 4084:Antimicrobial Agents and Chemotherapy 2484: 2478: 1789:Antimicrobial Agents and Chemotherapy 421:Fluoroquinolones prolong the heart's 89: 4906:"Quinolones: a comprehensive review" 4804: 4603:The quinolones: history and overview 3947: 3398: 3300:Current Medical Research and Opinion 3198:"Cardiotoxicity of fluoroquinolones" 2781:. U.S. Food and Drug Administration. 1726:– 2nd/3rd gen, related to difloxacin 1679:Quinolones have been widely used in 1608: 1500: 539: 334: 322:. The cause is not well understood. 5830: 4956:"Clinical Usefulness of Quinolones" 4732: 4647:. FDA. 4 April 2017. Archived from 4377:. Academic Press. pp. 119–154. 4278:The Journal of Biological Chemistry 3274:Goldfrank's toxicologic emergencies 3196:Rubinstein E, Camm J (April 2002). 3014:Clinical Microbiology and Infection 2792:Slimings C, Riley TV (April 2014). 1690:– 2nd gen, related to ciprofloxacin 1557: 1459: 1343:Although not formally a quinolone, 803: 13: 5048:. Associated Press. Archived from 4824:10.1093/oxfordjournals.jac.a020889 4524:Treatments in Respiratory Medicine 3680:Current Allergy and Asthma Reports 3628:10.1097/01.mop.0000192520.48411.fa 2877:Owens RC, Ambrose PG (July 2005). 1720:– 3rd gen, related to sparfloxacin 1714:– 3rd gen, related to levofloxacin 1708:– 3rd gen, related to levofloxacin 745: 723:. Most of them are named with the 282: 14: 6108: 5111:U.S. Food and Drug Administration 5089:to help reach a consensus. › 5068: 5016:. 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Food and Drug Administration 3171:The Journal of Family Practice 2124:(inactive 18 September 2024). 2058: 2041: 1997: 1915: 1825: 1776: 1761: 1391: 890:Tooltip Volume of distribution 1: 5500:Trimethoprim/sulfamethoxazole 5074: 4739:Burton TM (6 November 2015). 4601:Norris S, Mandell GL (1988). 4291:10.1016/S0021-9258(18)42185-0 4057:10.1016/S1473-3099(06)70599-0 3787:10.1016/S0960-894X(97)00324-7 3616:Current Opinion in Pediatrics 3413:10.1592/phco.21.16.253S.33993 2565:The Annals of Pharmacotherapy 2487:The Annals of Pharmacotherapy 1730: 1661:(removed from clinical use). 754:, so are often used to treat 4417:10.1016/0167-4781(83)90090-8 4237:Clinical Infectious Diseases 4136:Emerging Infectious Diseases 3968:10.1016/j.amjmed.2004.09.015 3919:Clinical Infectious Diseases 3855:Emerging Infectious Diseases 3806:Clinical Infectious Diseases 3585:10.1097/INF.0b013e3180cbd382 3549:10.1016/j.ejogrb.2008.12.007 3134:Clinical Infectious Diseases 2924:Food and Drug Administration 2883:Clinical Infectious Diseases 2542:10.1016/j.medmal.2006.05.012 2407:Journal of Athletic Training 2079:10.1097/INF.0b013e318245ab48 1983:10.1016/j.amjmed.2005.05.009 295:In 2008, the U.S. FDA added 277:multidrug-resistant bacteria 133:constitute a large group of 7: 5505:Ormetoprim/sulfadimethoxine 3442:Ford C, Law F (July 2014). 2957:Current Medicinal Chemistry 239: 10: 6113: 4494:10.2174/187152107779314179 3742:10.2174/187152107779314179 2852:10.1016/j.ijid.2012.07.010 2673:10.1001/jamasurg.2020.6165 2464:10.1016/j.phrs.2004.08.003 1326: 1312:= Dosage applies only to C 1311: 932:Tooltip Hepatic impairment 878:Tooltip Terminal half-life 721:6-position or C-8 position 601: 351: 312: 6047: 6025: 5982: 5972: 5935: 5907: 5886: 5829: 5757: 5709: 5643: 5634: 5586: 5558: 5523: 5515:Pyrimethamine/sulfadoxine 5492: 5442: 5379: 5351: 5272: 5257: 5207: 5185: 4910:American Family Physician 4852:American Family Physician 4231:Andriole VT (July 2005). 3692:10.1007/s11882-005-0049-1 2995:European Medicines Agency 2419:10.4085/1062-6050-49.2.09 2369:10.1007/s40264-013-0089-8 2326:10.1136/bmjoq-2024-002925 2176:10.1017/s1481803500015517 2019:10.1164/rccm.200405-644ST 1879:FEMS Microbiology Reviews 910: 903: 895: 883: 868: 856: 846: 836: 825: 818: 813: 530:benzodiazepine withdrawal 171:bacteria. One example is 144:related to the substance 121: 116: 102: 97: 83: 78: 66: 58: 53: 37: 28: 23: 5087:templates for discussion 5044:Schmid RE (1 May 2006). 3510:Le Infezioni in Medicina 3312:10.1185/030079907X188099 2969:10.2174/0929867013373435 2624:10.1136/bmj.314.7084.869 2499:10.1177/1060028013502457 2452:Pharmacological Research 2401:Lewis T, Cook J (2014). 1349:urinary tract infections 922:Tooltip Renal impairment 631:Streptococcus pneumoniae 625:Streptococcus pneumoniae 590:activity of this class ( 526:benzodiazepine-dependent 370: 4817:(Supplement 3): 17–24. 4768:Sanofi-Aventis U.S. LLC 4746:The Wall Street Journal 4566:Sanofi-Aventis U.S. LLC 4342:10.1126/science.1219192 3988:K08 HS14563 and HS11313 3449:. SMMGP. Archived from 3052:Mayo Clinic Proceedings 832:Tooltip Bioavailability 740:8-oxo-2'-deoxyguanosine 142:bicyclic core structure 5414:Sulfamethoxypyridazine 4991:. United Nations. 2005 4148:10.3201/eid0702.010239 4017:10.1001/jama.289.7.885 3867:10.3201/eid1103.040819 3407:(10 Pt 2): 253S–272S. 2889:(Suppl 2): S144–S157. 2779:(Microsoft PowerPoint) 2217:10.1542/peds.2011-1496 1742:public domain material 1433: 1340: 764:Legionella pneumophila 710:type II topoisomerases 701: 554:Ehlers-Danlos Syndrome 386:in the United States. 346:Ehlers-Danlos syndrome 306:mental health problems 268:central nervous system 200: 190: 6097:Quinolone antibiotics 5887:Newer non-fluorinated 5524:Other DHPS inhibitors 5510:Pyrimethamine/dapsone 5337:Succinylsulfathiazole 5333:Phthalylsulfathiazole 5217:2,4-Diaminopyrimidine 4721:. FDA. Archived from 4697:. FDA. Archived from 4096:10.1128/AAC.42.7.1778 3658:Janssen Pharmaceutica 1977:(Suppl 7A): 14S–20S. 1928:AMA Journal of Ethics 1422: 1355:during an attempt at 1334: 770:Mycoplasma pneumoniae 699: 615:Clostridium difficile 608:Antibiotic resistance 453:Mechanism of toxicity 431:, a life-threatening 358:Clostridium difficile 196: 186: 131:Quinolone antibiotics 5311:Acetyl sulfisoxazole 5170:inhibit nucleic acid 5121:17 June 2006 at the 5092:Quinolone antibiotic 4805:Ball P (July 2000). 4704:on 17 November 2015. 3812:(Suppl 2): S27–S72. 3495:17 June 2021 at the 3215:10.1093/jac/49.4.593 2319:(e002925): e002925. 1768:Andriole VT (1989). 1437:grouping of the non- 384:"black box" warnings 5686:Alalevonadifloxacin 5353:Intermediate-acting 5052:on 25 November 2007 4728:on 8 February 2016. 4452:10.1021/jm00103a013 4334:2012Sci...336..315F 4284:(19): 13150–13153. 3902:. pp. 542–546. 3369:Progres en Urologie 1407:Mechanism of Action 810: 692:Mechanism of action 568:to the drug class. 428:torsades de pointes 382:are the subject of 217:sickle-cell disease 215:Due to people with 62:Bacterial infection 6074:Never to phase III 5575:thereby inhibiting 5563:(inhibit bacterial 5409:Sulfametoxydiazine 5197:thereby inhibiting 5190:(inhibit bacterial 4770:(September 2008). 4672:on 20 October 2015 4568:(September 2008). 3660:(September 2008). 3243:The New York Times 3064:10.4065/81.12.1553 2931:on 30 October 2017 2811:10.1093/jac/dkt477 2749:10.1093/jac/dkt129 2711:. 20 December 2018 2536:(11–12): 697–705. 2242:. CNN. 8 July 2008 2210:(4): e1034–e1045. 1851:10.1093/jac/dkg212 1844:(Suppl S1): 1–11. 1434: 1341: 808: 702: 297:black box warnings 201: 191: 159:, which contain a 6084: 6083: 6043: 6042: 5968: 5967: 5931: 5930: 5882: 5881: 5554: 5553: 5488: 5487: 5193:purine metabolism 5023:978-81-312-1680-4 4446:(25): 4745–4750. 4243:(S2): S113–S119. 4197:10.1021/bi5000564 4191:(10): 1565–1574. 3781:(14): 1875–1878. 3478:. 29 August 2013. 3284:978-0-07-143763-9 3058:(12): 1553–1566. 2845:(11): e768–e773. 2577:10.1345/aph.1K347 2571:(11): 1859–1866. 2493:(10): 1359–1363. 1772:. Academic Press. 1609:Fourth generation 1605:(Ozex, Tosacin). 1501:Second generation 1324: 1323: 779:mitochondrial DNA 604:Antibiotic misuse 550:Marfan's syndrome 540:Contraindications 438:In 2019 study by 379:myasthenia gravis 335:Aortic dissection 233:are known to do. 128: 127: 54:Class identifiers 6104: 5980: 5979: 5947: 5946: 5682:Levonadifloxacin 5641: 5640: 5636:Fluoroquinolones 5584: 5583: 5389:Sulfadimethoxine 5361:Sulfamethoxazole 5282:Sulfaisodimidine 5270: 5269: 5205: 5204: 5159: 5152: 5145: 5136: 5135: 5116:Fluoroquinolones 5062: 5061: 5059: 5057: 5041: 5035: 5034: 5032: 5030: 5007: 5001: 5000: 4998: 4996: 4990: 4982: 4976: 4975: 4973: 4971: 4951: 4938: 4937: 4935: 4933: 4901: 4872: 4871: 4869: 4867: 4843: 4837: 4836: 4826: 4802: 4796: 4793: 4787: 4786: 4784: 4782: 4776: 4764: 4758: 4757: 4755: 4753: 4736: 4730: 4729: 4727: 4720: 4712: 4706: 4705: 4703: 4696: 4688: 4682: 4681: 4679: 4677: 4662: 4656: 4655: 4653: 4646: 4638: 4632: 4631: 4620: 4607: 4606: 4598: 4592: 4591: 4583: 4577: 4576: 4574: 4562: 4556: 4555: 4519: 4513: 4512: 4510: 4508: 4502: 4479: 4470: 4464: 4463: 4435: 4429: 4428: 4400: 4394: 4393: 4385: 4379: 4378: 4370: 4364: 4363: 4353: 4313: 4304: 4303: 4293: 4269: 4263: 4262: 4252: 4228: 4219: 4218: 4208: 4176: 4170: 4169: 4159: 4127: 4118: 4117: 4107: 4090:(7): 1778–1782. 4075: 4069: 4068: 4040: 4034: 4033: 4019: 3995: 3989: 3986: 3980: 3979: 3951: 3945: 3944: 3934: 3910: 3904: 3903: 3895: 3889: 3888: 3878: 3846: 3840: 3839: 3829: 3797: 3791: 3790: 3770: 3761: 3760: 3758: 3756: 3750: 3744:. Archived from 3727: 3718: 3712: 3711: 3675: 3669: 3668: 3666: 3654: 3648: 3647: 3611: 3605: 3604: 3567: 3561: 3560: 3532: 3526: 3525: 3505: 3499: 3486: 3480: 3479: 3472: 3466: 3465: 3463: 3461: 3455: 3448: 3439: 3433: 3432: 3396: 3385: 3384: 3375:(6): 1331–1334. 3364: 3358: 3357: 3355: 3353: 3347: 3338: 3332: 3331: 3306:(6): 1403–1413. 3295: 3289: 3288: 3268: 3262: 3261: 3259: 3257: 3234: 3228: 3227: 3217: 3193: 3187: 3186: 3166: 3160: 3159: 3149: 3125: 3119: 3118: 3082: 3076: 3075: 3046: 3040: 3039: 3029: 3005: 2999: 2998: 2997:. 11 March 2019. 2987: 2981: 2980: 2952: 2941: 2940: 2938: 2936: 2927:. Archived from 2915: 2909: 2908: 2898: 2874: 2865: 2864: 2854: 2830: 2824: 2823: 2813: 2789: 2783: 2782: 2780: 2771: 2762: 2761: 2751: 2742:(9): 1951–1961. 2727: 2721: 2720: 2718: 2716: 2701: 2695: 2694: 2684: 2652: 2646: 2645: 2635: 2603: 2597: 2596: 2560: 2554: 2553: 2525: 2519: 2518: 2482: 2476: 2475: 2447: 2441: 2440: 2430: 2398: 2389: 2388: 2352: 2339: 2338: 2328: 2313:BMJ Open Quality 2304: 2295: 2294: 2292: 2290: 2276: 2270: 2269: 2258: 2252: 2251: 2249: 2247: 2236: 2230: 2229: 2219: 2195: 2189: 2188: 2178: 2154: 2148: 2147: 2141: 2133: 2105: 2099: 2098: 2062: 2056: 2055: 2053: 2045: 2039: 2038: 2001: 1995: 1994: 1966: 1960: 1959: 1919: 1913: 1912: 1902: 1870: 1864: 1863: 1853: 1829: 1823: 1822: 1812: 1795:(7): 2161–2168. 1780: 1774: 1773: 1765: 1756: 1739: 1738: 1681:animal husbandry 1664:In development: 1558:Third generation 1468:(veterinary use) 1460:First generation 1319: 1245: 1241: 1077: 1073: 1068: 1064: 1059: 1052: 1045: 1041: 1024: 1012: 933: 929: 923: 919: 911:Dose adjustment 891: 887: 879: 875: 864: 860: 833: 829: 811: 807: 804:Pharmacokinetics 686:topoisomerase IV 680:at key sites in 655:acute bronchitis 647:Escherichia coli 566:hypersensitivity 499:antiviral agents 157:fluoroquinolones 112: 93: 42: 21: 20: 6112: 6111: 6107: 6106: 6105: 6103: 6102: 6101: 6087: 6086: 6085: 6080: 6079: 6064:Clinical trials 6039: 6021: 5987: 5964: 5940: 5927: 5903: 5878: 5825: 5753: 5705: 5630: 5578:DNA replication 5576: 5574: 5568: 5564: 5562: 5550: 5519: 5484: 5443:Other/ungrouped 5438: 5404:Sulfametomidine 5375: 5347: 5261: 5253: 5200: 5198: 5196: 5191: 5189: 5181: 5163: 5123:Wayback Machine 5090: 5071: 5066: 5065: 5055: 5053: 5042: 5038: 5028: 5026: 5024: 5008: 5004: 4994: 4992: 4988: 4984: 4983: 4979: 4969: 4967: 4952: 4941: 4931: 4929: 4902: 4875: 4865: 4863: 4844: 4840: 4803: 4799: 4794: 4790: 4780: 4778: 4774: 4765: 4761: 4751: 4749: 4737: 4733: 4725: 4718: 4714: 4713: 4709: 4701: 4694: 4690: 4689: 4685: 4675: 4673: 4664: 4663: 4659: 4651: 4644: 4640: 4639: 4635: 4630:. 26 July 2016. 4622: 4621: 4610: 4599: 4595: 4584: 4580: 4572: 4563: 4559: 4520: 4516: 4506: 4504: 4500: 4477: 4471: 4467: 4436: 4432: 4401: 4397: 4386: 4382: 4371: 4367: 4314: 4307: 4270: 4266: 4229: 4222: 4177: 4173: 4128: 4121: 4076: 4072: 4051:(10): 629–640. 4041: 4037: 3996: 3992: 3987: 3983: 3952: 3948: 3911: 3907: 3896: 3892: 3847: 3843: 3798: 3794: 3771: 3764: 3754: 3752: 3751:on 16 June 2010 3748: 3725: 3719: 3715: 3676: 3672: 3664: 3655: 3651: 3612: 3608: 3579:(10): 879–891. 3568: 3564: 3533: 3529: 3506: 3502: 3497:Wayback Machine 3487: 3483: 3474: 3473: 3469: 3459: 3457: 3453: 3446: 3440: 3436: 3401:Pharmacotherapy 3397: 3388: 3365: 3361: 3351: 3349: 3345: 3339: 3335: 3296: 3292: 3285: 3269: 3265: 3255: 3253: 3235: 3231: 3194: 3190: 3167: 3163: 3126: 3122: 3083: 3079: 3047: 3043: 3006: 3002: 2989: 2988: 2984: 2953: 2944: 2934: 2932: 2917: 2916: 2912: 2875: 2868: 2831: 2827: 2790: 2786: 2778: 2772: 2765: 2728: 2724: 2714: 2712: 2703: 2702: 2698: 2653: 2649: 2604: 2600: 2561: 2557: 2526: 2522: 2483: 2479: 2448: 2444: 2399: 2392: 2353: 2342: 2305: 2298: 2288: 2286: 2278: 2277: 2273: 2260: 2259: 2255: 2245: 2243: 2238: 2237: 2233: 2196: 2192: 2155: 2151: 2135: 2134: 2106: 2102: 2063: 2059: 2051: 2047: 2046: 2042: 2002: 1998: 1967: 1963: 1934:(10): 957–965. 1920: 1916: 1871: 1867: 1830: 1826: 1781: 1777: 1766: 1762: 1745: 1736: 1733: 1677: 1611: 1560: 1503: 1462: 1394: 1329: 1315: 1306: 1301: 1296: 1291: 1286: 1281: 1276: 1271: 1266: 1261: 1256: 1242: 1235: 1230: 1225: 1220: 1215: 1210: 1205: 1200: 1195: 1190: 1178: 1173: 1168: 1163: 1158: 1153: 1148: 1143: 1138: 1133: 1128: 1074: 1065: 1056: 1049: 1042: 1035: 1030: 1025: 1018: 1013: 1006: 994: 989: 984: 979: 974: 969: 964: 959: 954: 949: 944: 931: 921: 907: 898: 892: 889: 880: 877: 874: 865: 862: 853: 851: 843: 841: 831: 822: 806: 787: 748: 746:Cellular uptake 706:DNA replication 694: 610: 600: 558:QT prolongation 542: 534:cytochrome P450 467: 460: 455: 373: 354: 342:Marfan syndrome 337: 328: 320:Achilles tendon 315: 302:low blood sugar 293: 285: 283:Adverse effects 255:cystic fibrosis 242: 181: 108: 49: 17: 12: 11: 5: 6110: 6100: 6099: 6082: 6081: 6078: 6077: 6076: 6075: 6072: 6061: 6055: 6049: 6048: 6045: 6044: 6041: 6040: 6038: 6037: 6031: 6029: 6023: 6022: 6020: 6019: 6014: 6009: 6004: 5999: 5993: 5991: 5989:RNA polymerase 5977: 5970: 5969: 5966: 5965: 5963: 5962: 5956: 5954: 5951:Nitroimidazole 5944: 5933: 5932: 5929: 5928: 5926: 5925: 5919:Aminocoumarins 5915: 5913: 5905: 5904: 5902: 5901: 5896: 5890: 5888: 5884: 5883: 5880: 5879: 5877: 5876: 5871: 5866: 5861: 5856: 5851: 5846: 5841: 5835: 5833: 5827: 5826: 5824: 5823: 5821:Alatrofloxacin 5814: 5809: 5804: 5799: 5794: 5789: 5784: 5779: 5774: 5769: 5763: 5761: 5759:4th generation 5755: 5754: 5752: 5751: 5746: 5741: 5736: 5731: 5726: 5721: 5715: 5713: 5711:3rd generation 5707: 5706: 5704: 5703: 5698: 5693: 5688: 5675: 5670: 5665: 5660: 5655: 5649: 5647: 5645:2nd generation 5638: 5632: 5631: 5629: 5628: 5623: 5621:Piromidic acid 5618: 5616:Pipemidic acid 5613: 5608: 5606:Nalidixic acid 5603: 5598: 5592: 5590: 5588:1st generation 5581: 5556: 5555: 5552: 5551: 5549: 5548: 5543: 5538: 5533: 5527: 5525: 5521: 5520: 5518: 5517: 5512: 5507: 5502: 5496: 5494: 5490: 5489: 5486: 5485: 5483: 5482: 5477: 5472: 5470:Sulfaguanidine 5467: 5465:Sulfadicramide 5462: 5457: 5452: 5446: 5444: 5440: 5439: 5437: 5436: 5431: 5429:Sulfaphenazole 5426: 5421: 5416: 5411: 5406: 5401: 5396: 5391: 5385: 5383: 5377: 5376: 5374: 5373: 5368: 5363: 5357: 5355: 5349: 5348: 5346: 5345: 5340: 5326: 5325: 5324: 5314: 5304: 5294: 5289: 5287:Sulfamethizole 5284: 5278: 5276: 5267: 5264:DHPS inhibitor 5255: 5254: 5252: 5251: 5250: 5249: 5244: 5239: 5234: 5229: 5224: 5213: 5211: 5209:DHFR inhibitor 5202: 5183: 5182: 5166:Antibacterials 5162: 5161: 5154: 5147: 5139: 5133: 5132: 5126: 5113: 5104: 5098: 5070: 5069:External links 5067: 5064: 5063: 5036: 5022: 5010:Gupta (2009). 5002: 4977: 4939: 4916:(3): 455–464. 4873: 4862:on 6 June 2011 4838: 4797: 4788: 4759: 4731: 4707: 4683: 4657: 4654:on 9 May 2017. 4633: 4608: 4593: 4578: 4557: 4530:(6): 437–465. 4514: 4465: 4430: 4411:(4): 417–427. 4395: 4380: 4375:The quinolones 4365: 4305: 4264: 4250:10.1086/428051 4220: 4171: 4142:(2): 337–341. 4119: 4070: 4035: 4010:(7): 885–888. 3990: 3981: 3962:(3): 259–268. 3946: 3932:10.1086/512369 3925:(7): 977–980. 3905: 3890: 3861:(3): 380–384. 3841: 3818:10.1086/511159 3792: 3762: 3713: 3670: 3649: 3606: 3562: 3527: 3500: 3481: 3467: 3456:on 6 July 2017 3434: 3386: 3359: 3333: 3290: 3283: 3263: 3229: 3208:(4): 593–596. 3188: 3177:(4): 191–197. 3161: 3147:10.1086/591126 3140:(6): 735–743. 3120: 3093:(5): 359–378. 3077: 3041: 3020:(4): 370–378. 3000: 2982: 2963:(4): 371–384. 2942: 2910: 2896:10.1086/428055 2866: 2825: 2804:(4): 881–891. 2784: 2763: 2722: 2696: 2667:(3): 264–272. 2647: 2598: 2555: 2520: 2477: 2458:(3): 211–216. 2442: 2413:(3): 422–427. 2390: 2363:(9): 709–721. 2340: 2296: 2271: 2268:. 12 May 2016. 2253: 2231: 2190: 2169:(6): 459–462. 2149: 2116:(6): 524–531. 2112:(in Spanish). 2100: 2073:(5): 431–435. 2057: 2040: 2013:(4): 388–416. 1996: 1961: 1914: 1885:(2): 247–274. 1865: 1824: 1775: 1770:The Quinolones 1759: 1758: 1732: 1729: 1728: 1727: 1721: 1715: 1709: 1703: 1697: 1691: 1676: 1675:Veterinary use 1673: 1672: 1671: 1651: 1650: 1645: 1640: 1635: 1630: 1625: 1620: 1610: 1607: 1599: 1598: 1593: 1588: 1583: 1578: 1573: 1559: 1556: 1548: 1547: 1542: 1537: 1532: 1527: 1522: 1517: 1512: 1502: 1499: 1496:pipemidic acid 1492:piromidic acid 1488:nalidixic acid 1480: 1479: 1474: 1469: 1461: 1458: 1393: 1390: 1366:pipemidic acid 1345:nalidixic acid 1328: 1325: 1322: 1321: 1313: 1309: 1308: 1303: 1298: 1293: 1288: 1283: 1278: 1273: 1268: 1263: 1258: 1253: 1247: 1246: 1237: 1232: 1227: 1222: 1217: 1212: 1207: 1202: 1197: 1192: 1187: 1181: 1180: 1175: 1170: 1165: 1160: 1155: 1150: 1145: 1140: 1135: 1130: 1125: 1119: 1118: 1115: 1112: 1109: 1106: 1103: 1100: 1097: 1094: 1091: 1088: 1085: 1079: 1078: 1069: 1060: 1053: 1046: 1037: 1032: 1027: 1020: 1015: 1008: 1003: 997: 996: 991: 986: 981: 976: 971: 966: 961: 956: 951: 946: 941: 935: 934: 924: 913: 912: 909: 902: 894: 882: 872: 867: 855: 849: 845: 839: 835: 824: 817: 805: 802: 786: 783: 747: 744: 693: 690: 599: 596: 541: 538: 466: 463: 458: 454: 451: 447:kidney failure 396:cephalosporins 372: 369: 353: 350: 336: 333: 327: 326:Nervous system 324: 314: 311: 292: 291:Boxed warnings 289: 284: 281: 253:infections in 241: 238: 206:pyelonephritis 180: 177: 138:bacteriocidals 135:broad-spectrum 126: 125: 119: 118: 114: 113: 106: 100: 99: 98:External links 95: 94: 87: 81: 80: 76: 75: 70: 64: 63: 60: 56: 55: 51: 50: 43: 35: 34: 26: 25: 15: 9: 6: 4: 3: 2: 6109: 6098: 6095: 6094: 6092: 6073: 6071: 6068: 6067: 6065: 6062: 6059: 6056: 6054: 6051: 6050: 6046: 6036: 6033: 6032: 6030: 6028: 6024: 6018: 6015: 6013: 6010: 6008: 6005: 6003: 6000: 5998: 5995: 5994: 5992: 5990: 5985: 5981: 5978: 5975: 5971: 5961: 5958: 5957: 5955: 5952: 5948: 5945: 5943: 5938: 5934: 5924: 5920: 5917: 5916: 5914: 5911: 5906: 5900: 5897: 5895: 5892: 5891: 5889: 5885: 5875: 5872: 5870: 5869:Pradofloxacin 5867: 5865: 5862: 5860: 5859:Marbofloxacin 5857: 5855: 5852: 5850: 5847: 5845: 5842: 5840: 5837: 5836: 5834: 5832: 5828: 5822: 5818: 5817:Trovafloxacin 5815: 5813: 5810: 5808: 5807:Prulifloxacin 5805: 5803: 5800: 5798: 5797:Clinafloxacin 5795: 5793: 5790: 5788: 5785: 5783: 5780: 5778: 5775: 5773: 5770: 5768: 5765: 5764: 5762: 5760: 5756: 5750: 5747: 5745: 5742: 5740: 5737: 5735: 5732: 5730: 5729:Grepafloxacin 5727: 5725: 5722: 5720: 5717: 5716: 5714: 5712: 5708: 5702: 5699: 5697: 5694: 5692: 5689: 5687: 5683: 5679: 5676: 5674: 5671: 5669: 5666: 5664: 5661: 5659: 5656: 5654: 5653:Ciprofloxacin 5651: 5650: 5648: 5646: 5642: 5639: 5637: 5633: 5627: 5624: 5622: 5619: 5617: 5614: 5612: 5611:Oxolinic acid 5609: 5607: 5604: 5602: 5599: 5597: 5594: 5593: 5591: 5589: 5585: 5582: 5579: 5572: 5567: 5566:topoisomerase 5561: 5557: 5547: 5544: 5542: 5539: 5537: 5534: 5532: 5531:Acediasulfone 5529: 5528: 5526: 5522: 5516: 5513: 5511: 5508: 5506: 5503: 5501: 5498: 5497: 5495: 5491: 5481: 5478: 5476: 5473: 5471: 5468: 5466: 5463: 5461: 5458: 5456: 5455:Sulfacetamide 5453: 5451: 5448: 5447: 5445: 5441: 5435: 5432: 5430: 5427: 5425: 5424:Sulfamerazine 5422: 5420: 5417: 5415: 5412: 5410: 5407: 5405: 5402: 5400: 5397: 5395: 5392: 5390: 5387: 5386: 5384: 5382: 5378: 5372: 5369: 5367: 5364: 5362: 5359: 5358: 5356: 5354: 5350: 5344: 5343:Sulfathiourea 5341: 5338: 5334: 5330: 5329:Sulfathiazole 5327: 5323: 5320: 5319: 5318: 5317:Sulfanilamide 5315: 5312: 5308: 5307:Sulfafurazole 5305: 5302: 5301:Sulfasalazine 5298: 5297:Sulfapyridine 5295: 5293: 5292:Sulfadimidine 5290: 5288: 5285: 5283: 5280: 5279: 5277: 5275: 5271: 5268: 5265: 5260: 5256: 5248: 5245: 5243: 5240: 5238: 5237:Pyrimethamine 5235: 5233: 5230: 5228: 5225: 5223: 5220: 5219: 5218: 5215: 5214: 5212: 5210: 5206: 5203: 5194: 5188: 5184: 5179: 5175: 5171: 5167: 5160: 5155: 5153: 5148: 5146: 5141: 5140: 5137: 5130: 5127: 5124: 5120: 5117: 5114: 5112: 5108: 5105: 5102: 5099: 5097: 5093: 5088: 5084: 5083: 5078: 5073: 5072: 5051: 5047: 5040: 5025: 5019: 5015: 5014: 5006: 4987: 4981: 4965: 4961: 4957: 4950: 4948: 4946: 4944: 4927: 4923: 4919: 4915: 4911: 4907: 4900: 4898: 4896: 4894: 4892: 4890: 4888: 4886: 4884: 4882: 4880: 4878: 4861: 4857: 4853: 4849: 4842: 4834: 4830: 4825: 4820: 4816: 4812: 4808: 4801: 4792: 4773: 4769: 4763: 4748: 4747: 4742: 4735: 4724: 4717: 4711: 4700: 4693: 4687: 4671: 4667: 4661: 4650: 4643: 4637: 4629: 4625: 4619: 4617: 4615: 4613: 4604: 4597: 4589: 4582: 4571: 4567: 4561: 4553: 4549: 4545: 4541: 4537: 4533: 4529: 4525: 4518: 4499: 4495: 4491: 4487: 4483: 4476: 4469: 4461: 4457: 4453: 4449: 4445: 4441: 4434: 4426: 4422: 4418: 4414: 4410: 4406: 4399: 4391: 4384: 4376: 4369: 4361: 4357: 4352: 4347: 4343: 4339: 4335: 4331: 4327: 4323: 4319: 4312: 4310: 4301: 4297: 4292: 4287: 4283: 4279: 4275: 4268: 4260: 4256: 4251: 4246: 4242: 4238: 4234: 4227: 4225: 4216: 4212: 4207: 4202: 4198: 4194: 4190: 4186: 4182: 4175: 4167: 4163: 4158: 4153: 4149: 4145: 4141: 4137: 4133: 4126: 4124: 4115: 4111: 4106: 4101: 4097: 4093: 4089: 4085: 4081: 4074: 4066: 4062: 4058: 4054: 4050: 4046: 4039: 4032: 4027: 4023: 4018: 4013: 4009: 4005: 4001: 3994: 3985: 3977: 3973: 3969: 3965: 3961: 3957: 3950: 3942: 3938: 3933: 3928: 3924: 3920: 3916: 3909: 3901: 3894: 3886: 3882: 3877: 3872: 3868: 3864: 3860: 3856: 3852: 3845: 3837: 3833: 3828: 3823: 3819: 3815: 3811: 3807: 3803: 3796: 3788: 3784: 3780: 3776: 3769: 3767: 3747: 3743: 3739: 3735: 3731: 3724: 3717: 3709: 3705: 3701: 3697: 3693: 3689: 3685: 3681: 3674: 3663: 3659: 3653: 3645: 3641: 3637: 3633: 3629: 3625: 3621: 3617: 3610: 3602: 3598: 3594: 3590: 3586: 3582: 3578: 3574: 3566: 3558: 3554: 3550: 3546: 3542: 3538: 3531: 3523: 3519: 3515: 3511: 3504: 3498: 3494: 3490: 3489:2011 Document 3485: 3477: 3471: 3452: 3445: 3438: 3430: 3426: 3422: 3418: 3414: 3410: 3406: 3402: 3395: 3393: 3391: 3382: 3378: 3374: 3371:(in French). 3370: 3363: 3344: 3337: 3329: 3325: 3321: 3317: 3313: 3309: 3305: 3301: 3294: 3286: 3280: 3276: 3275: 3267: 3252: 3248: 3244: 3240: 3233: 3225: 3221: 3216: 3211: 3207: 3203: 3199: 3192: 3184: 3180: 3176: 3172: 3165: 3157: 3153: 3148: 3143: 3139: 3135: 3131: 3124: 3116: 3112: 3108: 3104: 3100: 3096: 3092: 3088: 3081: 3073: 3069: 3065: 3061: 3057: 3053: 3045: 3037: 3033: 3028: 3023: 3019: 3015: 3011: 3004: 2996: 2992: 2986: 2978: 2974: 2970: 2966: 2962: 2958: 2951: 2949: 2947: 2930: 2926: 2925: 2920: 2914: 2906: 2902: 2897: 2892: 2888: 2884: 2880: 2873: 2871: 2862: 2858: 2853: 2848: 2844: 2840: 2836: 2829: 2821: 2817: 2812: 2807: 2803: 2799: 2795: 2788: 2777: 2770: 2768: 2759: 2755: 2750: 2745: 2741: 2737: 2733: 2726: 2710: 2706: 2700: 2692: 2688: 2683: 2678: 2674: 2670: 2666: 2662: 2658: 2651: 2643: 2639: 2634: 2629: 2625: 2621: 2618:(7084): 869. 2617: 2613: 2609: 2602: 2594: 2590: 2586: 2582: 2578: 2574: 2570: 2566: 2559: 2551: 2547: 2543: 2539: 2535: 2531: 2524: 2516: 2512: 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1692: 1689: 1686: 1685: 1684: 1682: 1670: 1667: 1666: 1665: 1662: 1660: 1659:trovafloxacin 1656: 1649: 1646: 1644: 1641: 1639: 1638:prulifloxacin 1636: 1634: 1631: 1629: 1626: 1624: 1621: 1619: 1618:clinafloxacin 1616: 1615: 1614: 1606: 1604: 1597: 1594: 1592: 1589: 1587: 1584: 1582: 1579: 1577: 1576:grepafloxacin 1574: 1572: 1569: 1568: 1567: 1565: 1555: 1553: 1546: 1543: 1541: 1538: 1536: 1533: 1531: 1528: 1526: 1523: 1521: 1518: 1516: 1513: 1511: 1510:ciprofloxacin 1508: 1507: 1506: 1498: 1497: 1493: 1489: 1485: 1478: 1475: 1473: 1472:oxolinic acid 1470: 1467: 1464: 1463: 1457: 1455: 1451: 1450:ciprofloxacin 1447: 1442: 1440: 1431: 1427: 1421: 1417: 1415: 1412: 1408: 1404: 1400: 1389: 1385: 1381: 1377: 1375: 1371: 1370:oxolinic acid 1367: 1363: 1358: 1354: 1350: 1346: 1338: 1337:naphthyridine 1333: 1310: 1304: 1299: 1294: 1289: 1284: 1279: 1274: 1269: 1264: 1259: 1254: 1252: 1249: 1248: 1238: 1233: 1228: 1223: 1218: 1213: 1208: 1203: 1198: 1193: 1188: 1186: 1183: 1182: 1176: 1171: 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