Flumequine

Basic Info

Common NameFlumequine(F05652)
2D Structure
FRCD IDF05652
CAS Number42835-25-6
PubChem CID3374
FormulaC14H12FNO3
IUPAC Name

None

InChI Key

DPSPPJIUMHPXMA-UHFFFAOYSA-N

InChI

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)

Canonical SMILES

CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2)F)C(=O)O

Isomeric SMILES

CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2)F)C(=O)O

Synonyms
        
            flumequine
        
            42835-25-6
        
            Flumigal
        
            Apurone
        
            Flumequinum
        
            Flumequino
        
            Flumiquil
        
            Flumisol
        
            Imequyl
        
            Flumix
Classifies
                

                  
                    Pesticide
                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassQuinolines and derivatives
SubclassQuinoline carboxylic acids
Intermediate Tree NodesNot available
Direct ParentQuinoline carboxylic acids
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsQuinoline-3-carboxylic acid - Fluoroquinolone - Dihydroquinolone - Haloquinoline - Dihydroquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Benzenoid - Pyridine - Aryl fluoride - Aryl halide - Vinylogous amide - Heteroaromatic compound - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organohalogen compound - Organofluoride - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Properties

Property NameProperty Value
Molecular Weight261.252
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Complexity462
Monoisotopic Mass261.08
Exact Mass261.08
XLogP2.9
Formal Charge0
Heavy Atom Count19
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.6043
Human Intestinal AbsorptionHIA+0.9897
Caco-2 PermeabilityCaco2+0.7141
P-glycoprotein SubstrateNon-substrate0.5445
P-glycoprotein InhibitorNon-inhibitor0.8954
Non-inhibitor0.9794
Renal Organic Cation TransporterNon-inhibitor0.6957
Distribution
Subcellular localizationMitochondria0.4741
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7513
CYP450 2D6 SubstrateNon-substrate0.7781
CYP450 3A4 SubstrateNon-substrate0.5693
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9232
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.9710
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8682
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9176
Non-inhibitor0.9277
AMES ToxicityNon AMES toxic0.7007
CarcinogensNon-carcinogens0.9236
Fish ToxicityHigh FHMT0.9700
Tetrahymena Pyriformis ToxicityHigh TPT0.7477
Honey Bee ToxicityLow HBT0.7982
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7070
Carcinogenicity (Three-class)Non-required0.4894
Model Value Unit
Absorption
Aqueous solubility-3.7447LogS
Caco-2 Permeability1.1265LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4462LD50, mol/kg
Fish Toxicity0.7846pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5626pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle1011010European Union0.226/04/2017
Fat1011020European Union0.326/04/2017
Liver1011030European Union0.526/04/2017
Kidney1011040European Union1.526/04/2017
Muscle1012010European Union0.226/04/2017
Fat1012020European Union0.326/04/2017
Liver1012030European Union0.526/04/2017
Kidney1012040European Union1.526/04/2017
Muscle1013010European Union0.226/04/2017
Fat1013020European Union0.326/04/2017
Liver1013030European Union0.526/04/2017
Kidney1013040European Union1.526/04/2017
Muscle1014010European Union0.226/04/2017
Fat1014020European Union0.326/04/2017
Liver1014030European Union0.526/04/2017
Kidney1014040European Union1.526/04/2017
Muscle1015010European Union0.226/04/2017
Fat1015020European Union0.2526/04/2017
Liver1015030European Union0.526/04/2017
Kidney1015040European Union126/04/2017

References

TitleJournalDatePubmed ID
Antibiotic resistance of Aeromonas ssp. strains isolated from Sparus auratareared in Italian mariculture farms.Int J Food Microbiol2018 Aug 130081345
Molecular characterization and phylogenetic analysis of highly pathogenic Vibrio alginolyticus strains isolated during mortality outbreaks in cultured Ruditapesdecussatus juvenile.Microb Pathog2017 Oct28923608
Provisional epidemiological cutoff values for standard broth microdilutionsusceptibility testing of Flavobacterium columnare.J Fish Dis2017 May27717007
Antimicrobial susceptibility of Riemerella anatipestifer strains isolated fromgeese and ducks in Hungary.Acta Vet Hung2017 Jun28605957
Phylogenetic analysis of Escherichia coli isolated from broilers withcolibacillosis based on gyrA gene sequences.Can J Vet Res2017 Jan28154459
Effect of various storage conditions on the stability of quinolones in raw milk.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016Jul27258809
Analysis of flumequine enantiomers in rat plasma by UFLC-ESI-MS/MS.Chirality2016 Nov27791319
Use of micellar liquid chromatography to analyze oxolinic acid, flumequine,marbofloxacin and enrofloxacin in honey and validation according to the2002/657/EC decision.Food Chem2016 Jul 126920300
Cross-Contamination of Residual Emerging Contaminants and Antibiotic ResistantBacteria in Lettuce Crops and Soil Irrigated with Wastewater Treated bySunlight/H2O2.Environ Sci Technol2015 Sep 1526280108
Luminescent determination of quinolones in milk samples by liquidchromatography/post-column derivatization with terbium oxide nanoparticles.J Chromatogr A2015 Jul 3126077970
Multiresidue determination of fluoroquinolones in poultry muscle and kidneyaccording to the regulation 2002/657/EC. A systematic comparison of two differentapproaches: Liquid chromatography coupled to high-resolution mass spectrometry ortandem mass spectrometry.J Chromatogr A2015 Jan 3025577647
A europium- and terbium-coated magnetic nanocomposite as sorbent in dispersivesolid phase extraction coupled with ultra-high performance liquid chromatography for antibiotic determination in meat samples.J Chromatogr A2015 Dec 1826627586
Occurrence of veterinary antibiotics and progesterone in broiler manure andagricultural soil in Malaysia.Sci Total Environ2014 Aug 124836135
Antimicrobial resistance of Campylobacter jejuni and Campylobacter coli frompoultry in Italy.Microb Drug Resist2014 Apr24320689
Chemiluminescence competitive indirect enzyme immunoassay for 20 fluoroquinolone residues in fish and shrimp based on a single-chain variable fragment.Anal Bioanal Chem2013 Sep23842902
Direct determination of danofloxacin and flumequine in milk by use offluorescence spectrometry in combination with partial least-squares calibration.J Agric Food Chem2013 Mar 2023432704
Degradation of flumequine by the Fenton and photo-Fenton processes: evaluation ofresidual antimicrobial activity.Sci Total Environ2013 Feb 1523354374
Broilers as a source of quinolone-resistant and extraintestinal pathogenic Escherichia coli in the Czech Republic.Microb Drug Resist2013 Feb23020862
Flumequine enhances the in vivo mutagenicity of MeIQx in the mouse liver.Arch Toxicol2013 Aug23681119
Analysis of quinolone antibiotics in eggs: preparation and characterization of a raw material for method validation and quality control.Food Chem2012 Oct 125005999