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
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)
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia. | 2002 |
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| Bacterial resistance to quinolone antibiotics in Poland. | 2002 Apr |
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| Flumequine in Atlantic salmon Salmo salar: disposition in fish held in sea water versus fresh water. | 2002 Apr 24 |
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| Multiresidue determination of (fluoro)quinolone antibiotics in swine kidney using liquid chromatography-tandem mass spectrometry. | 2002 Apr 5 |
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| Prevalence of antimicrobial resistance among pigeon isolates of Streptococcus gallolyticus, Escherichia coli and Salmonella enterica serotype Typhimurium. | 2002 Aug |
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| Determination of quinolones and fluoroquinolones in fish tissue and seafood by high-performance liquid chromatography with electrospray ionisation tandem mass spectrometric detection. | 2002 Dec 20 |
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| Antimicrobial multiresistance in bacteria isolated from freshwater Chilean salmon farms. | 2002 Jul 3 |
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| Quantitative LC/MS-MS determination of sulfonamides and some other antibiotics in honey. | 2002 Jul-Aug |
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| Determination of ciprofloxacin, enrofloxacin and flumequine in pig plasma samples by capillary isotachophoresis--capillary zone electrophoresis. | 2002 May 25 |
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| High-performance liquid chromatographic method with fluorescence detection for the screening and quantification of oxolinic acid, flumequine and sarafloxacin in fish. | 2002 Nov 25 |
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| Validation of a liquid chromatography-tandem mass spectrometry method for the simultaneous quantification of 11 (fluoro)quinolone antibiotics in swine kidney. | 2002 Nov 8 |
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| Mechanistic study on flumequine hepatocarcinogenicity focusing on DNA damage in mice. | 2002 Oct |
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| [Fluoroquinolone susceptibility of Pseudomonas aeruginosa strains isolated from clinical materials]. | 2003 |
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| Evaluation of certain veterinary drug residues in food. | 2003 |
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| Comparative effects of fluoroquinolones on subsets of T lymphocytes in normothermic and hyperthermic mice. | 2003 Aug |
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| Explosive increase of Salmonella Java in poultry in the Netherlands: consequences for public health. | 2003 Feb |
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| Antimicrobial susceptibility of Riemerella anatipestifer isolated from ducks and the efficacy of ceftiofur treatment. | 2003 Jan |
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| Susceptibility of Listeria monocytogenes isolated from food in Italy to antibiotics. | 2003 Jun 25 |
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| Pharmacokinetics of flumequine and in vitro activity against bacterial pathogens of gilthead sea bream Sparus aurata. | 2003 Mar 17 |
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| Evaluation of certain veterinary drug residues in food. Sixty-second report of the Joint FAO/WHO Expert Committee on food additives. | 2004 |
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| The bryophyte Fontinalis antipyretica Hedw. bioaccumulates oxytetracycline, flumequine and oxolinic acid in the freshwater environment. | 2004 Apr 25 |
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| Development of an indirect competitive ELISA for flumequine residues in raw milk using chicken egg yolk antibodies. | 2004 Aug 11 |
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| Determination and on-line clean-up of (fluoro)quinolones in bovine milk using column-switching liquid chromatography fluorescence detection. | 2004 Dec 24 |
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| Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations. | 2005 Dec |
|
| Pharmacodynamics and pharmacokinetics of flumequine in pigs after single intravenous and intramuscular administration. | 2005 Jul |
|
| Introduction of the HPLC method for the determination of quinolone residues in various muscle tissues. | 2005 May |
|
| Vibrational spectroscopic characterization of fluoroquinolones. | 2005 May |
|
| Multiresidue determination of eleven quinolones in milk by liquid chromatography with fluorescence detection. | 2005 Nov-Dec |
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| Isolation and molecular characterization of quinolone resistant Salmonella spp. from poultry farms. | 2005 Oct 31 |
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| Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanisms, and transformation pathways. | 2005 Sep 15 |
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| Gene expression analysis in mice liver on hepatocarcinogenesis by flumequine. | 2006 Aug |
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| Fluoroquinolone-resistant Salmonella sp. in carcasses. | 2006 Feb |
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| Determination of fluoroquinolones in chicken tissues by LC-coupled electrospray ionisation and atmospheric pressure chemical ionisation. | 2006 Jan |
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| 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 |
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| Improved microbial screening assay for the detection of quinolone residues in poultry and eggs. | 2007 Aug |
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| Resistance mechanism against fluoroquinolones in Mycoplasma hyopneumoniae field isolates. | 2007 Fall |
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| Impacts of waste from concentrated animal feeding operations on water quality. | 2007 Feb |
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| Lack of in vivo mutagenicity and oxidative DNA damage by flumequine in the livers of gpt delta mice. | 2007 Jan |
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| Determination of quinolone residues in shrimp using liquid chromatography with fluorescence detection and residue confirmation by mass spectrometry. | 2007 Jul 23 |
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| Toxicity evaluation with Vibrio fischeri test of organic chemicals used in aquaculture. | 2007 Jun |
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| Multiresidue determination of quinolone antibacterials in eggs of laying hens by liquid chromatography with fluorescence detection. | 2007 Jun 1 |
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| 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 |
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| Biosensor immunoassay for flumequine in broiler serum and muscle. | 2007 Mar 14 |
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| Dual biosensor immunoassay-directed identification of fluoroquinolones in chicken muscle by liquid chromatography electrospray time-of-flight mass spectrometry. | 2007 Mar 14 |
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| Multiresidue determination of quinolone and fluoroquinolone antibiotics in fish and shrimp by liquid chromatography/tandem mass spectrometry. | 2007 Mar-Apr |
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| Simultaneous determination of trace levels of 10 quinolones in swine, chicken, and shrimp muscle tissues using HPLC with programmable fluorescence detection. | 2007 May 16 |
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| Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS. | 2007 Nov |
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| 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 |
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| Multiresidue HPLC analysis of ten quinolones in milk after solid phase extraction: validation according to the European Union Decision 2002/657/EC. | 2007 Oct |
|
| Oral bioavailability, tissue distribution and depletion of flumequine in the food producing animal, chicken for fattening. | 2008 Feb |
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.
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ACTIVE MOIETY
