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Urinary tract infections 207 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3356617	Curative		Withdrawn	Unknown Approved Use Unknown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
Effect of quinolone treatment on selection and persistence of quinolone-resistant Escherichia coli in swine faecal flora.	2005	16162248
Validation of a novel HPLC sorbent material for the determination of ten quinolones in human and veterinary pharmaceutical formulations.	2005 Dec	16405173
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 Jul-Aug	16156083
Oxidative transformation of fluoroquinolone antibacterial agents and structurally related amines by manganese oxide.	2005 Jun 15	16047783
Antimicrosporidial activity of (fluoro)quinolones in vitro and in vivo.	2005 May	16004377
Standardization of a broth microdilution susceptibility testing method to determine minimum inhibitory concentrations of aquatic bacteria.	2005 May 20	15997819
Flumequine in the goat: pharmacokinetics after intravenous and intramuscular administration.	2005 Nov	16369883
Efficacy of orally administered flumequine in the treatment of vibriosis caused by Listonella anguillarum in atlantic cod Gadus morhua.	2005 Nov 9	16385813
Multiresidue determination of eleven quinolones in milk by liquid chromatography with fluorescence detection.	2005 Nov-Dec	16526452
Isolation and molecular characterization of quinolone resistant Salmonella spp. from poultry farms.	2005 Oct 31	16153786
Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanisms, and transformation pathways.	2005 Sep 15	16201630
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
Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA).	2006 Apr 19	16608195
Ecotoxicity of mixtures of antibiotics used in aquacultures.	2006 Aug	16916040
Gene expression analysis in mice liver on hepatocarcinogenesis by flumequine.	2006 Aug	16468039
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 Dec 1	17027811
Determination of fluoroquinolones in milk samples by postcolumn derivatization liquid chromatography with luminescence detection.	2006 Dec 27	17177486
Fluoroquinolone-resistant Salmonella sp. in carcasses.	2006 Feb	17080579
Evaluation of the Premi Test and comparison with the One-Plate Test for the detection of antimicrobials in kidney.	2006 Feb	16449053
Determination of fluoroquinolones in chicken tissues by LC-coupled electrospray ionisation and atmospheric pressure chemical ionisation.	2006 Jan	16485718
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	16309690
Determination of quinolone residues in chicken and fish by capillary electrophoresis-mass spectrometry.	2006 Jun	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 Jun	16706907
Multiresidue method for the determination of quinolone antibiotics in bovine raw milk by capillary electrophoresis-tandem mass spectrometry.	2006 Nov 15	17105157
Chromatographic determination of flumequine in food samples by post-column derivatisation with terbium(III).	2006 Sep 25	17723715
Improved microbial screening assay for the detection of quinolone residues in poultry and eggs.	2007 Aug	17613071
Resistance mechanism against fluoroquinolones in Mycoplasma hyopneumoniae field isolates.	2007 Fall	17949302
Impacts of waste from concentrated animal feeding operations on water quality.	2007 Feb	17384784
[Residues of tetracycline and quinolones in wild fish living around a salmon aquaculture center in Chile].	2007 Feb	17369965
Biotransformation of flumequine by the fungus Cunninghamella elegans.	2007 Feb	17123578
Adsorption and oxidation of fluoroquinolone antibacterial agents and structurally related amines with goethite.	2007 Jan	17083963
Lack of in vivo mutagenicity and oxidative DNA damage by flumequine in the livers of gpt delta mice.	2007 Jan	16802149
Visible-light-Mediated TiO2 photocatalysis of fluoroquinolone antibacterial agents.	2007 Jul 1	17695920
Determination of quinolone residues in shrimp using liquid chromatography with fluorescence detection and residue confirmation by mass spectrometry.	2007 Jul 23	17631104
Separation of fifteen quinolones by high performance liquid chromatography: application to pharmaceuticals and ofloxacin determination in urine.	2007 Jun	17623463
Toxicity evaluation with Vibrio fischeri test of organic chemicals used in aquaculture.	2007 Jun	17292447
Multiresidue determination of quinolone antibacterials in eggs of laying hens by liquid chromatography with fluorescence detection.	2007 Jun 1	17241824
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	17511422
Microbiological detection of 10 quinolone antibiotic residues and its application to artificially contaminated poultry samples.	2007 Mar	17364926
Retention of quinolones on human serum albumin and alpha1-acid glycoprotein HPLC columns: relationships with different scales of lipophilicity.	2007 Mar	17169537
Biosensor immunoassay for flumequine in broiler serum and muscle.	2007 Mar 14	17386729
Dual biosensor immunoassay-directed identification of fluoroquinolones in chicken muscle by liquid chromatography electrospray time-of-flight mass spectrometry.	2007 Mar 14	17386721
Multiresidue determination of quinolone and fluoroquinolone antibiotics in fish and shrimp by liquid chromatography/tandem mass spectrometry.	2007 Mar-Apr	17474531
Simultaneous determination of trace levels of 10 quinolones in swine, chicken, and shrimp muscle tissues using HPLC with programmable fluorescence detection.	2007 May 16	17429982
Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS.	2007 Nov	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 Nov	17763524
Multiresidue HPLC analysis of ten quinolones in milk after solid phase extraction: validation according to the European Union Decision 2002/657/EC.	2007 Oct	17683042
Simultaneous determination of selected veterinary antibiotics in gilthead seabream (Sparus Aurata) by liquid chromatography-mass spectrometry.	2007 Sep 15	17644050
Oral bioavailability, tissue distribution and depletion of flumequine in the food producing animal, chicken for fattening.	2008 Feb	17950971

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