QuickView for Pefloxacin (compound)

Summary
General Info

PubChem

PubChem Compound 10892926

Name:	Pefloxacin
PubChem Compound ID:	10892926
Description:	A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.
Molecular formula:	C₁₇H₂₀FN₃O₃
Molecular weight:	332.36 g/mol

DrugBank

Identification

Name:	Pefloxacin
Name (isomeric):	DB00487
Drug Type:	small molecule
Description:	A synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria.
Brand:	Pefloxacinum [INN-Latin], Pefloxacino [INN-Spanish], Pefloxacin methanesulfonate, Pefloxacin mesylate, PFLX, Pefloxacine, Pefloxacin [INN-French]
Category:	Anti-Infective Agents, Nucleic Acid Synthesis Inhibitors
CAS number:	70458-92-3

Pharmacology

Indication:	For the treatment of uncomplicated gonococcal urethritis in males and for gram-negative-bacterial infections in the gastrointestinal system and the genitourinary tract.
Pharmacology:	Pefloxacin is a fluoroquinolone antibiotic. Flouroquinolones such as pefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigell... show more » Pefloxacin is a fluoroquinolone antibiotic. Flouroquinolones such as pefloxacin possess excellent activity against gram-negative aerobic bacteria such as E.coli and Neisseria gonorrhoea as well as gram-positive bacteria including S. pneumoniae and Staphylococcus aureus. They also posses effective activity against shigella, salmonella, campylobacter, gonococcal organisms, and multi drug resistant pseudomonas and enterobacter. show less «
Mechanism of Action:	The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target ... show more » The bactericidal action of pefloxacin results from interference with the activity of the bacterial enzymes DNA gyrase and topoisomerase IV, which are needed for the transcription and replication of bacterial DNA. DNA gyrase appears to be the primary quinolone target for gram-negative bacteria. Topoisomerase IV appears to be the preferential target in gram-positive organisms. Interference with these two topoisomerases results in strand breakage of the bacterial chromosome, supercoiling, and resealing. As a result DNA replication and transcription is inhibited. show less «
Absorption:	Well absorbed by the oral route.
Protein binding:	20-30%
Biotransformation:	Hepatic. Primary metabolites are pefloxacin N-oxide and norfloxacin.
Half Life:	8.6 hours
Toxicity:	Adverse reactions include peripheral neuropathy, nervousness, agitation, anxiety, and phototoxic events (rash, itching, burning) due to sunlight exposure.
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Drug interaction:

Magnesium	Formation of non-absorbable complexes
Iron Dextran	Formation of non-absorbable complexes
Aminophylline	Pefloxacin may increase the effect of aminophylline.
Calcium	Formation of non-absorbable complexes
Oxtriphylline	Pefloxacin may increase the effect of oxtriphylline.

Targets

DNA topoisomerase 4 subunit A

DNA gyrase subunit A

DNA gyrase negatively supercoils closed circular double- stranded DNA in an ATP-dependent manner and also catalyzes the interconversion of other topological isomers of double-stranded DNA rings, including catenanes and knotted rings

UniProt ID:

P43700

Gene:

gyrA

Actions:

inhibitor

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
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Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
View Article

Gootz TD, Zaniewski RP, Haskell SL, Kaczmarek FS, Maurice AE: Activities of trovafloxacin compared with those of other fluoroquinolones against purified topoisomerases and gyrA and grlA mutants of Staphylococcus aureus. Antimicrob Agents Chemother. 1999 Aug;43(8):1845-55.
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Bebear CM, Renaudin H, Charron A, Bove JM, Bebear C, Renaudin J: Alterations in topoisomerase IV and DNA gyrase in quinolone-resistant mutants of Mycoplasma hominis obtained in vitro. Antimicrob Agents Chemother. 1998 Sep;42(9):2304-11.
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Varon E, Houssaye S, Grondin S, Gutmann L: Nonmolecular test for detection of low-level resistance to fluoroquinolones in Streptococcus pneumoniae. Antimicrob Agents Chemother. 2006 Feb;50(2):572-9.
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Hombrouck C, Capmau ML, Moreau N: Overexpression, purification and photoaffinity labeling with a 3H-analogue of norfloxacin, of the GyrA and GyrB subunits of the DNA gyrase. Cell Mol Biol (Noisy-le-grand). 1999 May;45(3):347-52.
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Hooper DC: Quinolone mode of action--new aspects. Drugs. 1993;45 Suppl 3:8-14.
View Article

Fukuda H, Hori S, Hiramatsu K: Antibacterial activity of gatifloxacin (AM-1155, CG5501, BMS-206584), a newly developed fluoroquinolone, against sequentially acquired quinolone-resistant mutants and the norA transformant of Staphylococcus aureus. Antimicrob Agents Chemother. 1998 Aug;42(8):1917-22.
View Article

Drlica K, Zhao X: DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92.
View Article

DNA topoisomerase 2-alpha

Enzymes

Cytochrome P450 1A2