FLUMEQUINE

Possibly Marketed Outside US

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 Search

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

Molecular Formula	C14H12FNO3
Molecular Weight	261.2484
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3356617 | http://www.eongroup.net.bd/Admin/photos/Flumequine.pdf

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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://www.eongroup.net.bd/Admin/photos/Flumequine.pdf	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3356617	Curative		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Oral bioavailability, tissue distribution and depletion of flumequine in the food producing animal, chicken for fattening.	2008-02	17950971
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.	2007-11	17932875
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.	2007-11	17763524
Multiresidue HPLC analysis of ten quinolones in milk after solid phase extraction: validation according to the European Union Decision 2002/657/EC.	2007-10	17683042
Simultaneous determination of selected veterinary antibiotics in gilthead seabream (Sparus Aurata) by liquid chromatography-mass spectrometry.	2007-09-15	17644050
Improved microbial screening assay for the detection of quinolone residues in poultry and eggs.	2007-08	17613071
Determination of quinolone residues in shrimp using liquid chromatography with fluorescence detection and residue confirmation by mass spectrometry.	2007-07-23	17631104
Visible-light-Mediated TiO2 photocatalysis of fluoroquinolone antibacterial agents.	2007-07-01	17695920
Development of a monoclonal antibody-based broad-specificity ELISA for fluoroquinolone antibiotics in foods and molecular modeling studies of cross-reactive compounds.	2007-06-15	17511422
Multiresidue determination of quinolone antibacterials in eggs of laying hens by liquid chromatography with fluorescence detection.	2007-06-01	17241824
Separation of fifteen quinolones by high performance liquid chromatography: application to pharmaceuticals and ofloxacin determination in urine.	2007-06	17623463
Toxicity evaluation with Vibrio fischeri test of organic chemicals used in aquaculture.	2007-06	17292447
Simultaneous determination of trace levels of 10 quinolones in swine, chicken, and shrimp muscle tissues using HPLC with programmable fluorescence detection.	2007-05-16	17429982
Multiresidue determination of quinolone and fluoroquinolone antibiotics in fish and shrimp by liquid chromatography/tandem mass spectrometry.	2007-05-04	17474531
Biosensor immunoassay for flumequine in broiler serum and muscle.	2007-03-14	17386729
Dual biosensor immunoassay-directed identification of fluoroquinolones in chicken muscle by liquid chromatography electrospray time-of-flight mass spectrometry.	2007-03-14	17386721
Microbiological detection of 10 quinolone antibiotic residues and its application to artificially contaminated poultry samples.	2007-03	17364926
Retention of quinolones on human serum albumin and alpha1-acid glycoprotein HPLC columns: relationships with different scales of lipophilicity.	2007-03	17169537
Impacts of waste from concentrated animal feeding operations on water quality.	2007-02	17384784
[Residues of tetracycline and quinolones in wild fish living around a salmon aquaculture center in Chile].	2007-02	17369965
Biotransformation of flumequine by the fungus Cunninghamella elegans.	2007-02	17123578
Adsorption and oxidation of fluoroquinolone antibacterial agents and structurally related amines with goethite.	2007-01	17083963
Lack of in vivo mutagenicity and oxidative DNA damage by flumequine in the livers of gpt delta mice.	2007-01	16802149
Resistance mechanism against fluoroquinolones in Mycoplasma hyopneumoniae field isolates.	2007	17949302
Determination of fluoroquinolones in milk samples by postcolumn derivatization liquid chromatography with luminescence detection.	2006-12-27	17177486
Confirmatory and quantitative analysis using experimental design for the extraction and liquid chromatography-UV, liquid chromatography-mass spectrometry and liquid chromatography-mass spectrometry/mass spectrometry determination of quinolones in turkey muscle.	2006-12-01	17027811
Multiresidue method for the determination of quinolone antibiotics in bovine raw milk by capillary electrophoresis-tandem mass spectrometry.	2006-11-15	17105157
Chromatographic determination of flumequine in food samples by post-column derivatisation with terbium(III).	2006-09-25	17723715
Ecotoxicity of mixtures of antibiotics used in aquacultures.	2006-08	16916040
Gene expression analysis in mice liver on hepatocarcinogenesis by flumequine.	2006-08	16468039
Determination of quinolone residues in chicken and fish by capillary electrophoresis-mass spectrometry.	2006-06	16736458
Drug resistance and random amplified polymorphic DNA analysis of Photobacterium damselae ssp. piscicida isolates from cultured Seriola (yellowtail, amberjack and kingfish) in Japan.	2006-06	16706907
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).	2006-04-19	16608195
Multiresidue determination of eleven quinolones in milk by liquid chromatography with fluorescence detection.	2006-03-11	16526452
Fluoroquinolone-resistant Salmonella sp. in carcasses.	2006-02	17080579
Evaluation of the Premi Test and comparison with the One-Plate Test for the detection of antimicrobials in kidney.	2006-02	16449053
Efficient approach for the reliable quantification and confirmation of antibiotics in water using on-line solid-phase extraction liquid chromatography/tandem mass spectrometry.	2006-01-20	16309690
Determination of fluoroquinolones in chicken tissues by LC-coupled electrospray ionisation and atmospheric pressure chemical ionisation.	2006-01	16485718
Evaluation of certain veterinary drug residues in food. Sixty-sixth report of the Joint FAO/WHO Expert Committee on Food Additives.	2006	17373572
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	16878343
Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations.	2005-12	16405173
Efficacy of orally administered flumequine in the treatment of vibriosis caused by Listonella anguillarum in atlantic cod Gadus morhua.	2005-11-09	16385813
Flumequine in the goat: pharmacokinetics after intravenous and intramuscular administration.	2005-11	16369883
Isolation and molecular characterization of quinolone resistant Salmonella spp. from poultry farms.	2005-10-31	16153786
Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanisms, and transformation pathways.	2005-09-15	16201630
Multiresidue method for simultaneous determination of ten quinolone antibacterial residues in multimatrix/multispecies animal tissues by liquid chromatography with fluorescence detection: single laboratory validation study.	2005-09-15	16156083
Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide.	2005-06-15	16047783
Standardization of a broth microdilution susceptibility testing method to determine minimum inhibitory concentrations of aquatic bacteria.	2005-05-20	15997819
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.	2005-05	16004377
Effect of quinolone treatment on selection and persistence of quinolone-resistant Escherichia coli in swine faecal flora.	2005	16162248

Patents

Sample Use Guides

In Vivo Use Guide

400 mg bd. Duration of treatment ranged from 7-15 days

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:29:31 GMT 2025` Edited by `admin` on `Wed Apr 02 09:29:31 GMT 2025`
Record UNII	UVG8VSP2SJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APURONE

Preferred Name

English

FLUMEQUINE

Official Name

English

FLUMEQUINE [USAN]

Common 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