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)

HIDE SMILES / InChI

Molecular Formula	C17H20FN3O3
Molecular Weight	333.3574
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
[Neurologic side effects of fluoroquinolones. Apropos of 9 cases concerning pefloxacin].	1992 Sep-Oct	1299981
Purification and inhibition by quinolones of DNA gyrases from Mycobacterium avium, Mycobacterium smegmatis and Mycobacterium fortuitum bv. peregrinum.	1999 Sep	10517605
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
[Efficacy of pefoxacin (abactal) in the complex treatment of patients with pancreonecrosis].	2001	11558450
[Effect of pefloxacin on immune response].	2001	11550499
Evidence of different profiles of side effects and drug-drug interactions among the quinolones--the pharmacokinetic standpoint.	2001	11549786
History of quinolones and their side effects.	2001	11549783
[Comparative efficacy and safety of ciprofloxacin, ofloxacin, and pefloxacin in treatment of respiratory infections in children with cystic fibrosis].	2001	11548276
Occurrence of variants with temperature-dependent susceptibility (TDS) to antibiotics among Stenotrophomonas maltophilia clinical strains.	2001	11501404
[Effect of subinhibitory levels of aminoglycosides and fluoroquinolines on hydrophobicity and motility of Serratia marcescens].	2001 Feb	11233670
Studies on the significance of positive bacterial semen cultures in male fertility in Nigeria.	2001 Jul-Aug	11563831
Treatment of focal segmental glomerulosclerosis.	2001 Mar	11224693
Comparative in-vitro activities of commonly available quinolones and other antibiotics on bacterial isolates in Ibadan, Nigeria.	2001 Mar-Jun	14510147
Selective separation and simultaneous determination of trace levels of five types of fluorinated quinolone drugs by thin-layer chromatography/fluorescence densitometry.	2001 May-Jun	11417631
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Pharmacokinetics of fluoroquinolones in uncompensated cirrhosis: the significance of penetration in the ascitic fluid.	2001 Nov	11711259
[Study of pefloxacin concentration in blood and sputum in the aged pneumonia patients with impairment of renal function].	2001 Oct	11770420
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.	2001 Oct	11683796
[On fluoroquinolones treatment safety in children (clinical, morphological and catamnesis data)].	2002	12619515
Susceptibility of Enterobacteriaceae to beta-lactam agents and fluoroquinolones: a 3-year survey in France.	2002 Apr	12047412
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002 Jan	11821174
The choice of antibiotic in open fractures in a teaching hospital in a developing country.	2002 Jun	12137444
Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2.	2002 Jun 15	12110375
Optimization and validation of a CZE method for rufloxacin hydrochloride determination in coated tablets.	2002 Jun 15	12049980
[Bacteriologic examination of gallbladder contents].	2002 May-Jun	12170867
Antibiotic sensitivity and resistance profile of the micro-organisms responsible for urinary tract infection observed in Kashmir, India.	2002 Nov	12797637
[Diagnosis and treatment of legionella pneumonia].	2002 Nov	12442211
[Study of filter-paper-substrate delay fluorescence of three quinolones].	2003 Apr	12961880
Activities of 13 quinolones by three susceptibility testing methods against a collection of Haemophilus influenzae isolates with different levels of susceptibility to ciprofloxacin: evidence for cross-resistance.	2003 Jan	12493800
Pharmacokinetics and tissue penetration of pefloxacin plus metronidazole after administration as surgical prophylaxis in colorectal surgery.	2003 Jun	12816179
[Experience in using the new drug moxifloxacin (Avelox, "Bayer", Germaniia) in urologic practice].	2003 May-Jun	12846092
Reappraisal with meta-analysis of the addition of Gram-positive prophylaxis to fluoroquinolone in neutropenic patients.	2003 Nov 15	14615441
Mechanisms of pefloxacin-induced pain.	2004 Apr	15452594
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004 Apr	15047530
A three-way comparative study on the efficacy of twin sol to gel systems and marketed eye drops of pefloxacin mesylate.	2004 Aug	15321031
In vitro discrimination of fluoroquinolones toxicity on tendon cells: involvement of oxidative stress.	2004 Jan	14569066
Isolation of E. coli from foam and effects of fluoroquinolones on E. coli and foam production in male Japanese quail.	2004 Nov	15451247
Models for time-varying covariates in population pharmacokinetic-pharmacodynamic analysis.	2004 Oct	15373929

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:05:26 GMT 2023` Edited by `admin` on `Sat Dec 16 18:05:26 GMT 2023`
Record UNII	2H52Z9F2Q5
Record Status	`Validated (UNII)`
Record Version

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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