Pefloxacin

Pefloxacin
Clinical data
ATC code
Pharmacokinetic data
Bioavailability100%
Protein binding20–30%
MetabolismHepatic
Elimination half-life8.6 hours
ExcretionMostly renal, also biliary
Identifiers
IUPAC name
  • 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)
SMILES
  • O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCN(C)CC3)CC
InChI
  • 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

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

Licensed uses

  • Uncomplicated gonococcal urethritis in males.[2]
  • Bacterial infections in the gastrointestinal system.[2]
  • Genitourinary tract infections.[2]
  • Gonorrhoea. however this indication 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

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

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

  1. ↑ Generics (UK) Limited v. Daiichi Pharmaceutical Co. Ltd & Daiichi Sankyo Co. Ltd, 2016-07-13 (EWHC 15 October 2008).Text
  2. 1 2 3 http://www.pefloxacin.com/pefloxacin_usage.htm
  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. ↑ http://www.pefloxacin.com/pefloxacin_other.html
  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/.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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