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

Details

Stereochemistry RACEMIC
Molecular Formula C14H12FNO3
Molecular Weight 261.2484
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUMEQUINE

SMILES

CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O

InChI

InChIKey=DPSPPJIUMHPXMA-UHFFFAOYSA-N
InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)

HIDE SMILES / InChI
Flumequine is a synthetic antibiotic, which used to treat urinary tract infections until toxicity studies were reported. Flumequine inhibits bacterial enzyme DNA gyrase (topoisomerase) that is responsible for the supercoiling of DNA, thus bacterial cell growth disrupted by inhibiting nucleic acid synthesis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
Synthesis, characterization and antitumor activity of quinolone-platinum(II) conjugates.
2001 Dec 1
Pathogenicity and drug susceptibility of the Pasteurella anatis isolated in chickens in Taiwan.
2001 Jul-Sep
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia.
2002
Flumequine in Atlantic salmon Salmo salar: disposition in fish held in sea water versus fresh water.
2002 Apr 24
[Fluoroquinolone susceptibility of Pseudomonas aeruginosa strains isolated from clinical materials].
2003
Evaluation of certain veterinary drug residues in food.
2003
Comparative effects of fluoroquinolones on subsets of T lymphocytes in normothermic and hyperthermic mice.
2003 Aug
Susceptibility of Listeria monocytogenes isolated from food in Italy to antibiotics.
2003 Jun 25
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.
2004 Apr
Development of an indirect competitive ELISA for flumequine residues in raw milk using chicken egg yolk antibodies.
2004 Aug 11
Preliminary investigation on the environmental occurrence and effects of antibiotics used in aquaculture in Italy.
2004 Feb
Isocratic reversed-phase high-performance liquid chromatographic separation of tetracyclines and flumequine controlled by a chaotropic effect.
2004 Mar 26
Mechanisms of quinolone resistance and clonal relationship among Aeromonas salmonicida strains isolated from reared fish with furunculosis.
2004 Sep
Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide.
2005 Jun 15
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.
2005 May
Introduction of the HPLC method for the determination of quinolone residues in various muscle tissues.
2005 May
Flumequine in the goat: pharmacokinetics after intravenous and intramuscular administration.
2005 Nov
Isolation and molecular characterization of quinolone resistant Salmonella spp. from poultry farms.
2005 Oct 31
High-throughput screening for multi-class veterinary drug residues in animal muscle using liquid chromatography/tandem mass spectrometry with on-line solid-phase extraction.
2006
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).
2006 Apr 19
Efficient approach for the reliable quantification and confirmation of antibiotics in water using on-line solid-phase extraction liquid chromatography/tandem mass spectrometry.
2006 Jan 20
Determination of quinolone residues in chicken and fish by capillary electrophoresis-mass spectrometry.
2006 Jun
Drug resistance and random amplified polymorphic DNA analysis of Photobacterium damselae ssp. piscicida isolates from cultured Seriola (yellowtail, amberjack and kingfish) in Japan.
2006 Jun
Multiresidue method for the determination of quinolone antibiotics in bovine raw milk by capillary electrophoresis-tandem mass spectrometry.
2006 Nov 15
Adsorption and oxidation of fluoroquinolone antibacterial agents and structurally related amines with goethite.
2007 Jan
Determination of quinolone residues in shrimp using liquid chromatography with fluorescence detection and residue confirmation by mass spectrometry.
2007 Jul 23
Toxicity evaluation with Vibrio fischeri test of organic chemicals used in aquaculture.
2007 Jun
Development of a monoclonal antibody-based broad-specificity ELISA for fluoroquinolone antibiotics in foods and molecular modeling studies of cross-reactive compounds.
2007 Jun 15
Retention of quinolones on human serum albumin and alpha1-acid glycoprotein HPLC columns: relationships with different scales of lipophilicity.
2007 Mar
Biosensor immunoassay for flumequine in broiler serum and muscle.
2007 Mar 14
Simultaneous determination of trace levels of 10 quinolones in swine, chicken, and shrimp muscle tissues using HPLC with programmable fluorescence detection.
2007 May 16
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.
2007 Nov
Development and validation of an HPLC confirmatory method for residue analysis of ten quinolones in tissues of various food-producing animals, according to the European Union Decision 2002/657/EC.
2007 Nov
Simultaneous determination of selected veterinary antibiotics in gilthead seabream (Sparus Aurata) by liquid chromatography-mass spectrometry.
2007 Sep 15
Patents

Sample Use Guides

400 mg bd. Duration of treatment ranged from 7-15 days
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: It was investigated the potential of flumequine to inhibit eukaryotic topoisomerase II, which is responsible for the double-strand DNA breakage reaction as well as bacterial gyrase, inhibitory effects of flumequine on topoisomerase II were high relative to the influence on bacterial gyrase.
Unknown
Name Type Language
FLUMEQUINE
EP   HSDB   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
FLUMEQUINE [USAN]
Common Name English
APURONE
Brand Name English
FLUMEQUINE [MI]
Common Name English
FLUMEQUINE [MART.]
Common Name English
flumequine [INN]
Common Name English
FLUMEQUINE [HSDB]
Common Name English
6,7-DIHYDRO-9-FLUORO-5-METHYL-1-OXO-1H,5H-BENZO(I,J)QUINOLIZINE-2-CARBOXYLIC ACID
Common Name English
1H,5H-BENZO(IJ)QUINOLIZINE-2-CARBOXYLIC ACID, 9-FLUORO-6,7-DIHYDRO-5-METHYL-1-OXO-
Common Name English
Flumequine [WHO-DD]
Common Name English
FLUMEQUINE [EP MONOGRAPH]
Common Name English
NSC-757806
Code English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
WHO-VATC QJ01MB07
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
WHO-ATC J01MB07
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
Code System Code Type Description
RXCUI
25112
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY RxNorm
SMS_ID
100000080686
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PRIMARY
ECHA (EC/EINECS)
255-962-6
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL370252
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
CHEBI
85267
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
FDA UNII
UVG8VSP2SJ
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PRIMARY
DRUG BANK
DB08972
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PRIMARY
EPA CompTox
DTXSID5045623
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
MESH
C012976
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
WIKIPEDIA
FLUMEQUINE
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
EVMPD
SUB07696MIG
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
NCI_THESAURUS
C80639
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
HSDB
7034
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PRIMARY
PUBCHEM
3374
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
CAS
42835-25-6
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
NSC
757806
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
INN
3776
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY
MERCK INDEX
m5438
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
1197
Created by admin on Sat Dec 16 17:43:54 GMT 2023 , Edited by admin on Sat Dec 16 17:43:54 GMT 2023
PRIMARY