U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of FLEROXACIN

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

Description
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

Curator's Comment: In 1986 fleroxacin was licensed to F.Hoffmann-La Roche (Switzerland).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
QUINODIS

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Activity of ciprofloxacin and other fluorinated quinolones against mycobacteria.
1987 Apr 27
Comparative in-vitro activity of fleroxacin and other 6-fluoroquinolones against mycobacteria.
1988 Oct
Adverse reactions in a dose-ranging study with a new long-acting fluoroquinolone, fleroxacin.
1989 Oct
The antimicrobial activity of Fleroxacin RO 23-6240, a third generation fluoroquinolone derivative, tested in vitro.
1990
Central nervous system toxicity of quinolones: human and animal findings.
1990 Oct
Comparative in vitro and in vivo activity of fleroxacin and ofloxacin against various mycobacteria.
1991 Sep
In-vitro activities of quinolones against mycobacteria.
1993 Dec
Activity of topoisomerase inhibitors against Pneumocystis carinii in vitro and in an inoculated mouse model.
1993 Jul
Two cases of fleroxacin-induced insomnia.
1994 Winter
Trovafloxacin is active against Toxoplasma gondii.
1996 Aug
[In vitro anti-MAC activities of new quinolones in focus (2)].
1996 Sep
Atypical pneumonia in the Nordic countries: aetiology and clinical results of a trial comparing fleroxacin and doxycycline. Nordic Atypical Pneumonia Study Group.
1997 Apr
Fleroxacin 400 mg once daily versus ofloxacin 400 mg twice daily in skin and soft tissue infections.
1997 Sep-Oct
High-performance liquid chromatographic assay of fleroxacin in human serum using fluorescence detection.
2001 Sep 13
Separation and determination of seven fluoroquinolones by pressurized capillary electrochromatography.
2005 Nov
High-throughput metal susceptibility testing of microbial biofilms.
2005 Oct 3
[Determination of fleroxacin by photochemical fluorescence of zinc-fleroxacin complex].
2005 Sep
The use of microscopy and three-dimensional visualization to evaluate the structure of microbial biofilms cultivated in the Calgary Biofilm Device.
2006
[Clinical observation on shufei granule in improving right ventricular function of patients with chronic pulmonary heart disease].
2006 Aug
Interaction between fluoroquinolones and bovine serum albumin studied by affinity capillary electrophoresis.
2006 Dec
Moxifloxacin enhances antiproliferative and apoptotic effects of etoposide but inhibits its proinflammatory effects in THP-1 and Jurkat cells.
2006 Oct 23
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
[Study on the ternary complex of FLRX, zinc(II) and BSA by the method of fluorescence].
2007 Apr
1H and 19F NMR relaxation studies of fleroxacin with Micrococcus luteus.
2007 Apr 11
Solution equilibria between aluminum(III) ion and some fluoroquinolone family members. Spectroscopic and potentiometric study.
2007 Dec
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
A rapid CE-potential gradient detection method for determination of quinolones.
2007 Nov
Utility of a single adjusting compartment: a novel methodology for whole body physiologically-based pharmacokinetic modelling.
2008 Aug 8
Ionic liquids as mobile phase additives for the high-performance liquid chromatographic analysis of fluoroquinolone antibiotics in water samples.
2008 Dec
Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae.
2008 Jun
[Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry].
2008 May
Quantitative comparison of the convulsive activity of combinations of twelve fluoroquinolones with five nonsteroidal antiinflammatory agents.
2009
Synergistic antitumor effects of fleroxacin with 5-fluorouracil in vitro and in vivo for bladder cancer cell lines.
2009 Dec
Capillary electrophoresis with electrochemiluminescence detection for simultaneous determination of proline and fleroxacin in human urine.
2009 Feb
[Interaction of cucurbit[8]urils with ofloxacin, fleroxacin, gatifloxacin and sparfloxacin].
2009 Feb
[Simultaneous determination of 19 quinolone residues in honey using high performance liquid chromatography-tandem mass spectrometry].
2009 Jan
CE determination of quinolones in the presence of bovine serum albumin.
2009 Jan
A comparison of fluoroquinolones versus other antibiotics for treating enteric fever: meta-analysis.
2009 Jun 3
Application of ionic liquids in high performance reversed-phase chromatography.
2009 Jun 4
Rapid determination of 19 quinolone residues in spiked fish and pig muscle by high-performance liquid chromatography (HPLC) tandem mass spectrometry.
2009 Mar
Urinary tract infections and reduced risk of bladder cancer in Los Angeles.
2009 Mar 10
Enhanced separation of seven quinolones by capillary electrophoresis with silica nanoparticles as additive.
2009 Mar 15
Inter- and intramolecular photochemical reactions of fleroxacin.
2009 May 7
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
Multifocal aggressive squamous cell carcinomas induced by prolonged voriconazole therapy: a case report.
2010
Biopsy proven acute interstitial nephritis after treatment with moxifloxacin.
2010 Aug 23
Comparative in vitro activity of Meropenem, Imipenem and Piperacillin/tazobactam against 1071 clinical isolates using 2 different methods: a French multicentre study.
2010 Mar 18
Determination of fluoroquinolone antibiotics in environmental water samples based on magnetic molecularly imprinted polymer extraction followed by liquid chromatography-tandem mass spectrometry.
2010 Mar 3
Preparation of high-affinity rabbit monoclonal antibodies for ciprofloxacin and development of an indirect competitive ELISA for residues in milk.
2010 Oct
Cephalosporin Resistance in Neisseria gonorrhoeae.
2010 Sep
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.
Name Type Language
FLEROXACIN
INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:28:56 GMT 2023 , Edited by admin on Fri Dec 15 15:28:56 GMT 2023
WHO-ATC J01MA08
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NCI_THESAURUS C795
Created by admin on Fri Dec 15 15:28:56 GMT 2023 , Edited by admin on Fri Dec 15 15:28:56 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1177
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PRIMARY
EVMPD
SUB07639MIG
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SMS_ID
100000080993
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WIKIPEDIA
FLEROXACIN
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MERCK INDEX
m5401
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PRIMARY Merck Index
CHEBI
31810
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PRIMARY
INN
5966
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PRIMARY
CAS
79660-72-3
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PRIMARY
PUBCHEM
3357
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PRIMARY
USAN
Y-48
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PRIMARY
CHEMBL
CHEMBL6273
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PRIMARY
NCI_THESAURUS
C72657
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PRIMARY
MESH
D016576
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DRUG BANK
DB04576
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EPA CompTox
DTXSID1046714
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FDA UNII
N804LDH51K
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RXCUI
42322
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PRIMARY RxNorm