Pefloxacin

Pefloxacin
Clinical data
ATC code	J01MA03 (WHO) ;
Pharmacokinetic data
Bioavailability	100%
Protein binding	20–30%
Metabolism	Hepatic
Elimination half-life	8.6 hours
Excretion	Mostly renal, also biliary
Identifiers
	IUPAC name 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid;
CAS Number	70458-92-3 ;
PubChem CID	51081;
DrugBank	DB00487 ;
ChemSpider	46291 ;
UNII	2H52Z9F2Q5;
KEGG	D02306 ;
ChEBI	CHEBI:50199 ;
ChEMBL	ChEMBL267648 ;
CompTox Dashboard (EPA)	DTXSID3048493 ;
ECHA InfoCard	100.067.807
Chemical and physical data
Formula	C17H20FN3O3
Molar mass	333.363 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:FHFYDNQZQSQIAI-UHFFFAOYSA-N ;
	(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 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.

External links

[1] Generics (UK) Limited v. Daiichi Pharmaceutical Co. Ltd & Daiichi Sankyo Co. Ltd, 2016-07-13 (EWHC 15 October 2008), Text.

[p_usage-2] "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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