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 |
|---|---|---|
| Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques. | 2000 Oct |
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| Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening. | 2000 Oct |
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| Synthesis, characterization and antitumor activity of quinolone-platinum(II) conjugates. | 2001 Dec 1 |
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| Pathogenicity and drug susceptibility of the Pasteurella anatis isolated in chickens in Taiwan. | 2001 Jul-Sep |
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| Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia. | 2002 |
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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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| [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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| Susceptibility of Listeria monocytogenes isolated from food in Italy to antibiotics. | 2003 Jun 25 |
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| Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
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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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| Preliminary investigation on the environmental occurrence and effects of antibiotics used in aquaculture in Italy. | 2004 Feb |
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| Isocratic reversed-phase high-performance liquid chromatographic separation of tetracyclines and flumequine controlled by a chaotropic effect. | 2004 Mar 26 |
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| Mechanisms of quinolone resistance and clonal relationship among Aeromonas salmonicida strains isolated from reared fish with furunculosis. | 2004 Sep |
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| Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide. | 2005 Jun 15 |
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| Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo. | 2005 May |
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| Introduction of the HPLC method for the determination of quinolone residues in various muscle tissues. | 2005 May |
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| Flumequine in the goat: pharmacokinetics after intravenous and intramuscular administration. | 2005 Nov |
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| Isolation and molecular characterization of quinolone resistant Salmonella spp. from poultry farms. | 2005 Oct 31 |
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| 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 |
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| Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA). | 2006 Apr 19 |
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| 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 |
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| Determination of quinolone residues in chicken and fish by capillary electrophoresis-mass spectrometry. | 2006 Jun |
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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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| Multiresidue method for the determination of quinolone antibiotics in bovine raw milk by capillary electrophoresis-tandem mass spectrometry. | 2006 Nov 15 |
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| Adsorption and oxidation of fluoroquinolone antibacterial agents and structurally related amines with goethite. | 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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| 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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| Retention of quinolones on human serum albumin and alpha1-acid glycoprotein HPLC columns: relationships with different scales of lipophilicity. | 2007 Mar |
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| Biosensor immunoassay for flumequine in broiler serum and muscle. | 2007 Mar 14 |
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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 |
|
| 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.
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C012976
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FLUMEQUINE
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ACTIVE MOIETY
