Pefloxacin is a

quinolone antibiotic A quinolone antibiotic is a member of a large group of broad-spectrum bacteriocidals that share a bicyclic core structure related to the substance 4-quinolone. They are used in human and veterinary medicine to treat bacterial infections, as we ...

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.

Licensed uses

*Uncomplicated gonococcal urethritis in males.http://www.pefloxacin.com/pefloxacin_usage.htm *Bacterial infections in the gastrointestinal system. *Genitourinary tract infections. *Gonorrhoea. however this indication is no longer effective due to bacterial resistance. Pefloxacin has been increasingly used as a veterinary medicine to treat microbial infections.

Mode of action

Pefloxacin is a

broad-spectrum antibiotic A broad-spectrum antibiotic is an antibiotic that acts on the two major bacterial groups, Gram-positive and Gram-negative, or any antibiotic that acts against a wide range of disease-causing bacteria. These medications are used when a bacterial inf ...

that is active against both

Gram-positive In bacteriology, gram-positive bacteria are bacteria that give a positive result in the Gram stain test, which is traditionally used to quickly classify bacteria into two broad categories according to their type of cell wall. Gram-positive bacte ...

and

Gram-negative Gram-negative bacteria are bacteria that do not retain the crystal violet stain used in the Gram staining method of bacterial differentiation. They are characterized by their cell envelopes, which are composed of a thin peptidoglycan cell wall ...

bacteria. It functions by inhibiting

DNA gyrase DNA gyrase, or simply gyrase, is an enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrat ...

, a type II

topoisomerase DNA topoisomerases (or topoisomerases) are enzymes that catalyze changes in the topological state of DNA, interconverting relaxed and supercoiled forms, linked (catenated) and unlinked species, and knotted and unknotted DNA. Topological issues i ...

, and topoisomerase IV, 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. 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.

Synthesis

The

Gould–Jacobs reaction The Gould–Jacobs reaction is an organic synthesis for the preparation of quinolines and 4‐hydroxyquinoline derivatives. The Gould-Jacobs reaction is a series of reactions. The series of reactions begins with the condensation/substitution of an a ...

between 3-Chloro-4-fluoroaniline 67-21-5(1) and Diethyl methoxymethylenemalonate 0131-09-7gives Ethyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate 0458-93-4 5073-15-3(2). Alkylation with iodoethane 5-03-6in the presence of sodium hydride base leads t
CID:12733855
(3). Nucleophilic aromatic displacement of the chloride at the 7-position with methylpiperazine 09-01-3resulted in 1530-83-8(4). Saponification of the ester leads to pefloxacin (5).

References

External links

How Stuff Works - Cipro

Package insert information
{Dead link, date=May 2020 , bot=InternetArchiveBot , fix-attempted=yes 1,4-di-hydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acids Fluoroquinolone antibiotics Piperazines