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Pefloxacin

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(Redirected from C17H20FN3O3)
Pefloxacin
Clinical data
ATC code
Pharmacokinetic data
Bioavailability100%
Protein binding20–30%
MetabolismHepatic
Elimination half-life8.6 hours
ExcretionMostly renal, also biliary
Identifiers
  • 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.067.807 Edit this at Wikidata
Chemical and physical data
FormulaC17H20FN3O3
Molar mass333.363 g·mol−1
3D model (JSmol)
  • O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCN(C)CC3)CC
  • InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24) checkY
  • Key:FHFYDNQZQSQIAI-UHFFFAOYSA-N checkY
  (verify)

Pefloxacin is a quinolone antibiotic used to treat bacterial infections. Pefloxacin has not been approved for use in the United States.

History

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Pefloxacin was developed in 1979 and approved in France for human use in 1985.[1]

Licensed uses

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  • Uncomplicated gonococcal urethritis in males.[2]
  • Bacterial infections in the gastrointestinal system.[2]
  • Genitourinary tract infections.[2]
  • Gonorrhoea, however, this use is no longer effective due to bacterial resistance.[3]

Pefloxacin has been increasingly used as a veterinary medicine to treat microbial infections.[4]

Mode of action

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Pefloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV,[5] which is an enzyme necessary to separate, replicated DNA, thereby inhibiting cell division.

Adverse effects

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Tendinitis and rupture, usually of the Achilles tendon, are class-effects of the fluoroquinolones, most frequently reported with pefloxacin.[6] The estimated risk of tendon damage during pefloxacin therapy has been estimated by the French authorities in 2000 to be 1 case per 23,130 treatment days as compared to ciprofloxacin where it has been estimated to be 1 case per 779,600.[7]

References

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  1. ^ Generics (UK) Limited v. Daiichi Pharmaceutical Co. Ltd & Daiichi Sankyo Co. Ltd, 2016-07-13 (EWHC 15 October 2008), Text.
  2. ^ a b c "Reasons for prescribing Pefloxacin". pefloxacin.com. Archived from the original on 2016-03-05.
  3. ^ Centers for Disease Control and Prevention (CDC) (April 2007). "Update to CDC's sexually transmitted diseases treatment guidelines, 2006: fluoroquinolones no longer recommended for treatment of gonococcal infections". MMWR Morb. Mortal. Wkly. Rep. 56 (14): 332–6. PMID 17431378.
  4. ^ "Alternative uses for Pefloxacin". pefloxacin.com. Archived from the original on 2016-06-17.
  5. ^ Drlica K, Zhao X (1 September 1997). "DNA gyrase, topoisomerase IV, and the 4-quinolones". Microbiol Mol Biol Rev. 61 (3): 377–92. doi:10.1128/mmbr.61.3.377-392.1997. PMC 232616. PMID 9293187.
  6. ^ Khaliq Y, Zhanel GG (October 2005). "Musculoskeletal injury associated with fluoroquinolone antibiotics". Clin Plast Surg. 32 (4): 495–502, vi. doi:10.1016/j.cps.2005.05.004. PMID 16139623.
  7. ^ Casparian JM, Luchi M, Moffat RE, Hinthorn D (May 2000). "Quinolones and tendon ruptures". South. Med. J. 93 (5): 488–91. doi:10.1097/00007611-200093050-00008. PMID 10832946.
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