Pefloxacin
Antibiotic
- J01MA03 (WHO)
- 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
- 70458-92-3
Y
- 51081
- DB00487 Y
- 46291 Y
- 2H52Z9F2Q5
- D02306 Y
- CHEBI:50199 Y
- ChEMBL267648 Y
- DTXSID3048493
- Interactive image
- 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)Y
- Key:FHFYDNQZQSQIAI-UHFFFAOYSA-NY
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 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
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
- ^ Generics (UK) Limited v. Daiichi Pharmaceutical Co. Ltd & Daiichi Sankyo Co. Ltd, 2016-07-13 (EWHC 15 October 2008), Text.
- ^ a b c "Reasons for prescribing Pefloxacin". pefloxacin.com. Archived from the original on 2016-03-05.
- ^ 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.
- ^ "Alternative uses for Pefloxacin". pefloxacin.com. Archived from the original on 2016-06-17.
- ^ 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.
- ^ 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.
- ^ 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.
- v
- t
- e
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
| DHFR inhibitor | |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Sulfonamides (DHPS inhibitor) |
| ||||||||
| Combinations |
| ||||||||
| Other DHPS inhibitors |
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
| 1st generation | |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Fluoroquinolones |
| ||||||||
| Newer non-fluorinated | |||||||||
| Related (DG) |
inhibitors
| Nitroimidazole derivatives | |
|---|---|
| Nitrofuran derivatives |
| Rifamycins/ RNA polymerase | |
|---|---|
| Lipiarmycins |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
External links
- How Stuff Works - Cipro
- Package insert information[permanent dead link]
