FLEROXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18F3N3O3
Molecular Weight	369.3383
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC1)C2=C(F)C=C3C(=O)C(=CN(CCF)C3=C2F)C(O)=O

InChI

InChIKey=XBJBPGROQZJDOJ-UHFFFAOYSA-N

InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula	C17H18F3N3O3
Molecular Weight	369.3383
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8861529
Curator's Comment: description was created based on several sources, including, http://www.kccp.or.kr/erp/erpmenus/journal_contents/upLoadFiles/18(2)-132(08-24)(p.132~136).pdf

Fleroxacin is an anti-bacterial agent developed for the treatment of uncomplicated cystitis in women, uncomplicated gonococcal infections, bacterial enteritis, and traveler's diarrea, urinary tract infection, pyelonephritis, skin, soft tissue, bone and joint infections, and lower respiratory tract infections. Fleroxacin acts on bacterials by inhibiting DNA gyrase and topoisomerase IV. Although the current status of the drug in Europe and in the USA is unknown, there is information about its approval and usage in China.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://www.kccp.or.kr/erp/erpmenus/journal_contents/upLoadFiles/18(2)-132(08-24)(p.132~136).pdf	Inhibitor 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://www.kccp.or.kr/erp/erpmenus/journal_contents/upLoadFiles/18(2)-132(08-24)(p.132~136).pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: http://www.ncbi.nlm.nih.gov/pubmed/8861529	Curative		Approved 8429	QUINODIS Approved Use Unknown

PubMed

Title	Date	PubMed
Activity of ciprofloxacin and other fluorinated quinolones against mycobacteria.	1987 Apr 27	3107379
Comparative in-vitro activity of fleroxacin and other 6-fluoroquinolones against mycobacteria.	1988 Oct	3144550
Adverse reactions in a dose-ranging study with a new long-acting fluoroquinolone, fleroxacin.	1989 Oct	2511802
Comparative in vitro and in vivo activity of fleroxacin and ofloxacin against various mycobacteria.	1991 Sep	1771676
In-vitro activities of quinolones against mycobacteria.	1993 Dec	8144420
Activity of topoisomerase inhibitors against Pneumocystis carinii in vitro and in an inoculated mouse model.	1993 Jul	8395791
Atypical pneumonia in the Nordic countries: aetiology and clinical results of a trial comparing fleroxacin and doxycycline. Nordic Atypical Pneumonia Study Group.	1997 Apr	9145823
Fleroxacin 400 mg once daily versus ofloxacin 400 mg twice daily in skin and soft tissue infections.	1997 Sep-Oct	9309373
History of quinolones and their side effects.	2001	11549783
Quinolones alter defense reactions mediated by macrophages.	2001 Feb	11360919
Effects of fluoroquinolones on the locomotor activity in rats.	2001 Mar	11357519
Protective effect of fleroxacin against the nephrotoxicity of isepamicin in rats.	2002 Apr	11995935
[In vitro antibacterial activity of prulifloxacin, a new oral fluoroquinolone].	2002 Dec	12621732
Ciprofloxacin induces apoptosis and inhibits proliferation of human colorectal carcinoma cells.	2002 Feb 1	11875713
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002 Jan	11821174
[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration].	2002 Jun	12199111
Visible absorption spectra of the 4f electron transitions of neodymium, praseodymium, holmium and erbium complexes with fleroxacin and their analytical application.	2002 May	12036131
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation.	2002 May 27	12034313
Antimicrobial postexposure prophylaxis for anthrax: adverse events and adherence.	2002 Oct	12396927
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004 Apr	15047530
Spectrofluorimetric study of the charge-transfer complexation of certain fluoroquinolones with 7,7,8,8-tetracyanoquinodimethane.	2005 Jan 1	15556451
High-throughput metal susceptibility testing of microbial biofilms.	2005 Oct 3	16202124
The use of microscopy and three-dimensional visualization to evaluate the structure of microbial biofilms cultivated in the Calgary Biofilm Device.	2006	17242736
Interaction between fluoroquinolones and bovine serum albumin studied by affinity capillary electrophoresis.	2006 Dec	17159308
Moxifloxacin enhances antiproliferative and apoptotic effects of etoposide but inhibits its proinflammatory effects in THP-1 and Jurkat cells.	2006 Oct 23	17047652
Preparation of anti-pefloxacin antibody and development of an indirect competitive enzyme-linked immunosorbent assay for detection of pefloxacin residue in chicken liver.	2006 Sep 20	16968054
1H and 19F NMR relaxation studies of fleroxacin with Micrococcus luteus.	2007 Apr 11	17254731
A flow injection chemiluminescence method for the determination of fluoroquinolone derivative using the reaction of luminol and hydrogen peroxide catalyzed by gold nanoparticles.	2007 May 15	19071726
A rapid CE-potential gradient detection method for determination of quinolones.	2007 Nov	17941113
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].	2009 Jan	19449537
A comparison of fluoroquinolones versus other antibiotics for treating enteric fever: meta-analysis.	2009 Jun 3	19493939
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.	2009 Mar	19680903
Fluoroquinolone antibiotic determination in bovine, ovine and caprine milk using solid-phase extraction and high-performance liquid chromatography-fluorescence detection with ionic liquids as mobile phase additives.	2009 Oct 23	19268960

Patents

Sample Use Guides

In Vivo Use Guide

400mg once daily (uncomplicated cystitis in women, uncomplicated gonococcal infections, bacterial enteritis, and traveler's diarrhea), 200 mg administered for 3 days (uncomplicated urinary tract infection).

Route of Administration: Oral

In Vitro Use Guide

In vitro activity of fleroxacin was tested against different bacteria isolates. The drug inhibited E.Coli (MIC 0.06-0.12 ug/ml), Klebsiella pneumoniae and K. oxytoca (MIC 0.12-1 ug/ml), Enterobacter cloacae and E. aerogenes (MIC <= 0.06-0.5 ug/ml), Citrobacterfreundii and C. diversus (MIC 0.06-1), Streptococcus faecalis (MIC 4-16 ug/ml), Pseudomonas aeruginosa (MIC 0.5-32 ug/ml), Salmonella spp. (MIC 0.06-0.12 ug/ml), etc.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:28:56 GMT 2023` Edited by `admin` on `Fri Dec 15 15:28:56 GMT 2023`
Record UNII	N804LDH51K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLEROXACIN

Official Name

English

RO-236240

Code

English

6,8-Difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid

Systematic Name

English

RO 23-6240/000

Code

English

MEGALOCIN

Brand Name

English

fleroxacin [INN]

Common Name

English

RO-236240000

Code

English

FLEROXACIN [MART.]

Common Name

English

RO-23-6240/000

Code

English

FLEROXACIN [USAN]

Common Name

English

MEGALONE

Brand Name

English

FLEROXACIN [JAN]

Common Name

English

Fleroxacin [WHO-DD]

Common Name

English

FLEROXACIN [MI]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 6,8-DIFLUORO-1-(2-FLUOROETHYL)-1,4-DIHYDRO-7-(4-METHYL-1-PIPERAZINYL)-4-OXO-

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01MA08