PEFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H20FN3O3
Molecular Weight	333.3574
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCN(C)CC3

InChI

InChIKey=FHFYDNQZQSQIAI-UHFFFAOYSA-N

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)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2663414 | http://pefloxacin.com/ | https://www.medindia.net/doctors/drug_information/pefloxacin.htm

Pefloxacin is a fluorinated quinolone that is structurally related to nalidixic acid. It can be administered both orally and intravenously, and has a broad spectrum of in vitro activity against Gram-negative organisms and staphylococci. 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. It is prescribed for the treatment of uncomplicated gonococcal urethritis in males and for gram-negative bacterial infections in gastrointestinal system and genitourinary tract.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase 26 Target ID: CHEMBL2094139 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3007757	Inhibitor 8297

PubMed

Title	Date	PubMed
Peripheral neuropathy associated with fluoroquinolones.	1992 Jul 11	1352007
The 2-pyridone antibacterial agents: 8-position modifications.	1999 Jul	10438895
Purification and inhibition by quinolones of DNA gyrases from Mycobacterium avium, Mycobacterium smegmatis and Mycobacterium fortuitum bv. peregrinum.	1999 Sep	10517605
Pefloxacin in steroid dependent and resistant idiopathic nephrotic syndrome.	2000 Jul-Aug	10946806
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000 Oct	10991859
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000 Oct	10991858
Eradicative effect of cotrimoxazole and quinolones on non-typhoid salmonellae.	2001	11763669
[Effect of pefloxacin on immune response].	2001	11550499
[Comparative efficacy and safety of ciprofloxacin, ofloxacin, and pefloxacin in treatment of respiratory infections in children with cystic fibrosis].	2001	11548276
[An experimental study on the release of endotoxin from gram negative bacteria induced by antibiotics].	2001 Apr	11876914
Pefloxacin and ciprofloxacin increase UVA-induced edema and immune suppression.	2001 Aug	11499539
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001 Dec 26	11754677
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].	2001 Feb	11265221
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].	2001 Feb	11233670
Pharmacokinetics of pefloxacin and its interaction with cyclosporin A, a P-glycoprotein modulator, in rat blood, brain and bile, using simultaneous microdialysis.	2001 Mar	11250882
Treatment of focal segmental glomerulosclerosis.	2001 Mar	11224693
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
[Study of pefloxacin concentration in blood and sputum in the aged pneumonia patients with impairment of renal function].	2001 Oct	11770420
[Efficacy of some new antibiotics in treating experimental brucellosis].	2002	12698575
Ciprofloxacin induces apoptosis and inhibits proliferation of human colorectal carcinoma cells.	2002 Feb 1	11875713
Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2.	2002 Jun 15	12110375
Adverse drug reactions related to the use of fluoroquinolone antimicrobials: an analysis of spontaneous reports and fluoroquinolone consumption data from three italian regions.	2003	12534327
A microarray-based antibiotic screen identifies a regulatory role for supercoiling in the osmotic stress response of Escherichia coli.	2003 Feb	12566398
[Drug sensitivity of Ureaplasma urealyticum, persisting in patients with chronic inflammatory diseases of the urogenital tract].	2003 Jul-Aug	12966887
Staphylococcus aureus carriage in selected communities and their antibiotic susceptibility patterns.	2003 Jun	14569746
Molecular epidemiology of ampicillin-resistant clinical isolates of Salmonella enterica serovar Typhimurium.	2003 Jun	12868659
Mechanisms of pefloxacin-induced pain.	2004 Apr	15452594
Some plasma and saliva pharmacokinetics parameters of rifampicin in the presence of pefloxacin.	2004 Jul-Aug	15266220
[Pharmacokinetics and dose adaptation of ofloxacine, pefloxacine and ciprofloxacine during haemodialysis and continuous ambulatory peritoneal dialysis].	2004 May	15243351

Patents

Sample Use Guides

In Vivo Use Guide

Oral: Adults - 400 mg bid 7 to 10 days taken along with food. IV Infusion: Adults - 400mg in 100ml of 5% dextrose slow infusion over 1 hr bid.

Route of Administration: Other

Name

Type

Language

PEFLOXACIN

Official Name

English

Pefloxacin [WHO-DD]

Common Name

English

PEFLOXACIN [USAN]

Common Name

English

1589-RB

Code

English

1589 RB

Code

English

pefloxacin [INN]

Common Name

English

1-ETHYL-6-FLUORO-7-(4-METHYLPIPERAZIN-1-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

Systematic Name

English

EU-5306

Code

English

PEFLOXACIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01MA03