PEFLOXACIN MESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H20FN3O3.CH4O3S
Molecular Weight	429.463
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.CCN1C=C(C(O)=O)C(=O)C2=C1C=C(N3CCN(C)CC3)C(F)=C2

InChI

InChIKey=HQQSBEDKMRHYME-UHFFFAOYSA-N

InChI=1S/C17H20FN3O3.CH4O3S/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;1-5(2,3)4/h8-10H,3-7H2,1-2H3,(H,23,24);1H3,(H,2,3,4)

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

Molecular Formula	CH4O3S
Molecular Weight	96.106
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 8504

PubMed

Title	Date	PubMed
Isolation of E. coli from foam and effects of fluoroquinolones on E. coli and foam production in male Japanese quail.	2004-11	15451247
Models for time-varying covariates in population pharmacokinetic-pharmacodynamic analysis.	2004-10	15373929
A three-way comparative study on the efficacy of twin sol to gel systems and marketed eye drops of pefloxacin mesylate.	2004-08	15321031
Some plasma and saliva pharmacokinetics parameters of rifampicin in the presence of pefloxacin.	2004-07-22	15266220
[Pharmacokinetics and dose adaptation of ofloxacine, pefloxacine and ciprofloxacine during haemodialysis and continuous ambulatory peritoneal dialysis].	2004-05	15243351
Antimicrobial resistance in commensal flora of pig farmers.	2004-05	15200822
Mechanisms of pefloxacin-induced pain.	2004-04	15452594
Effects of acetyl salicylate and ibuprofen on fluoroquinolone MICs on Salmonella enterica serovar typhimurium in vitro.	2004-04	15216945
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004-04	15047530
Extension of the isobolographic approach to interactions studies between more than two drugs: illustration with the convulsant interaction between pefloxacin, norfloxacin, and theophylline in rats.	2004-03	14762894
Effect of pefloxacin on the urinary excretion of rifampicin.	2004-01-06	14704591
In vitro discrimination of fluoroquinolones toxicity on tendon cells: involvement of oxidative stress.	2004-01	14569066
Antibiotics for preventing recurrent urinary tract infection in non-pregnant women.	2004	15266443
[Antibiotherapy in osteoarticular infections in children suffering from hemoglobinopathy in the University Teaching Hospital of Yopougon].	2003-12-25	14693473
X-ray powder diffraction patterns for certain fluoroquinolone antibiotic drugs.	2003-12	14769236
Activity of combinations of ceftazidime, imipenem and pefloxacin against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa.	2003-12	14659660
Dose ranging pharmacokinetics and brain distribution of norfloxacin using microdialysis in rats.	2003-12	14603491
Reappraisal with meta-analysis of the addition of Gram-positive prophylaxis to fluoroquinolone in neutropenic patients.	2003-11-15	14615441
[Enterobacterial susceptibility to antibiotics in northern Lebanon (1998-2001)].	2003-10-08	14530123
Comparative in-vitro activities of commonly available quinolones and other antibiotics on bacterial isolates in Ibadan, Nigeria.	2003-09-27	14510147
[Drug sensitivity of Ureaplasma urealyticum, persisting in patients with chronic inflammatory diseases of the urogenital tract].	2003-09-12	12966887
[Experience in using the new drug moxifloxacin (Avelox, "Bayer", Germaniia) in urologic practice].	2003-07-09	12846092
Fluoroquinolone-associated tendinopathy: a critical review of the literature.	2003-06-01	12766835
Staphylococcus aureus carriage in selected communities and their antibiotic susceptibility patterns.	2003-06	14569746
Antimicrobial sensitivity pattern of organisms causing urinary tract infection in children with sickle cell anaemia in Ibadan, Nigeria.	2003-06	14529216
Molecular epidemiology of ampicillin-resistant clinical isolates of Salmonella enterica serovar Typhimurium.	2003-06	12868659
Pharmacokinetics and tissue penetration of pefloxacin plus metronidazole after administration as surgical prophylaxis in colorectal surgery.	2003-06	12816179
Determination of the antibiotic drug pefloxacin in bulk form, tablets and human serum using square wave cathodic adsorptive stripping voltammetry.	2003-04-10	12667924
Microbial isolates in open fractures seen in the accident and emergency unit of a teaching hospital in a developing country.	2003-04-01	12665270
[Study of filter-paper-substrate delay fluorescence of three quinolones].	2003-04	12961880
The effect of nitric oxide combined with fluoroquinolones against Salmonella enterica serovar Typhimurium in vitro.	2003-04	12886427
A microarray-based antibiotic screen identifies a regulatory role for supercoiling in the osmotic stress response of Escherichia coli.	2003-02	12566398
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.	2003-01	12493800
[Formation of virulent antigen-modified mutants (Fra-, Fra-Tox-) of plague bacteria resistant to rifampicin and quinolones].	2003	13677133
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
In vitro antimicrobial interactions of arthemeter with some 4-quinolones.	2002-12-17	12481382
Antibiotic sensitivity and resistance profile of the micro-organisms responsible for urinary tract infection observed in Kashmir, India.	2002-11	12797637
[Tenotoxic potential of fluoroquinolones in the choice of surgical antibiotic prophylaxis in ophthalmology].	2002-11	12515937
[Diagnosis and treatment of legionella pneumonia].	2002-11	12442211
Some pharmacokinetic parameters of pefloxacin in lactating goats.	2002-10	12416870
Pharmacokinetics and tissue distribution of intravenous pefloxacin for antibiotic prophylaxis in biliary surgery.	2002-10	12355580
[Bacteriologic examination of gallbladder contents].	2002-08-13	12170867
[Pefloxacin (Abaktal)--efficacy in treating severe infections, optimization of treatment based on pharmacokinetic and pharmacodynamic parameters].	2002	12728632
[Efficacy of some new antibiotics in treating experimental brucellosis].	2002	12698575
[On fluoroquinolones treatment safety in children (clinical, morphological and catamnesis data)].	2002	12619515
[Pefloxacin in the treatment of patients with mucoviscidosis].	2002	12369138
Clinical role of protein binding of quinolones.	2002	12162760
[Neurologic side effects of fluoroquinolones. Apropos of 9 cases concerning pefloxacin].	1992-09-01	1299981
Peripheral neuropathy associated with fluoroquinolones.	1992-07-11	1352007
Non-nephrotoxic empiric antimicrobial therapy in febrile neutropenic cancer patients.	1992	1524911

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 `Mon Mar 31 18:25:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:56 GMT 2025`
Record UNII	5IAD0UV3FH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PEFLOXACIN MESILATE

Preferred Name

English

PEFLOXACIN MESYLATE

Official Name

English

PEFLOXACIN METHANESULFONATE ANHYDROUS [MI]

Common Name

English

1-ETHYL-6-FLUORO-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-3-QUINOLINECARBOXYLIC MESILATE

Systematic Name

English

PEFLOXACIN MESYLATE [USAN]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-, MONOMETHANESULFONATE

Common Name

English

PEFLOXACIN METHANESULFONATE

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-, MONOMETHANESULPHONATE

Common Name

English

NSC-758944

Code

English

Pefloxacin mesilate [WHO-DD]

Common Name

English

1-ETHYL-6-FLUORO-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-3-QUINOLINECARBOXYLIC MESYLATE

Systematic Name

English

41-982-RP

Code

English

PEFLOXACIN MESILATE [MART.]

Common Name

English

41 982 RP

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C795