Difloxacin

Basic Info

Common NameDifloxacin(F06161)
2D Structure
FRCD IDF06161
CAS Number98106-17-3
PubChem CID56206
FormulaC21H19F2N3O3
IUPAC Name

6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid

InChI Key

NOCJXYPHIIZEHN-UHFFFAOYSA-N

InChI

InChI=1S/C21H19F2N3O3/c1-24-6-8-25(9-7-24)19-11-18-15(10-17(19)23)20(27)16(21(28)29)12-26(18)14-4-2-13(22)3-5-14/h2-5,10-12H,6-9H2,1H3,(H,28,29)

Canonical SMILES

CN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F

Isomeric SMILES

CN1CCN(CC1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F

Synonyms
        
            3-Quinolinecarboxylic acid, 6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-
        
            Difloxacin
        
            98106-17-3
        
            Difloxacin [INN]
        
            6-fluoro-1-(4-fluorophenyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
        
            UNII-5Z7OO9FNFD
        
            Difloxacin (INN)
        
            C21H19F2N3O3
        
            5Z7OO9FNFD
        
            CHEBI:4537
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassQuinolines and derivatives
SubclassPhenylquinolines
Intermediate Tree NodesNot available
Direct ParentPhenylquinolines
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsPhenylquinoline - Quinoline-3-carboxylic acid - Fluoroquinolone - N-arylpiperazine - Aminoquinoline - Haloquinoline - Dihydroquinolone - Dihydroquinoline - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Tertiary aliphatic/aromatic amine - Dialkylarylamine - N-alkylpiperazine - N-methylpiperazine - Fluorobenzene - Halobenzene - Benzenoid - 1,4-diazinane - Pyridine - Monocyclic benzene moiety - Piperazine - Aryl halide - Aryl fluoride - Vinylogous amide - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Amino acid or derivatives - Amino acid - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Azacycle - Carboxylic acid - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Organic oxide - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Amine - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight399.398
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Complexity672
Monoisotopic Mass399.139
Exact Mass399.139
XLogP1.6
Formal Charge0
Heavy Atom Count29
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9680
Human Intestinal AbsorptionHIA+0.9910
Caco-2 PermeabilityCaco2+0.8792
P-glycoprotein SubstrateSubstrate0.7797
P-glycoprotein InhibitorNon-inhibitor0.9043
Non-inhibitor0.9071
Renal Organic Cation TransporterNon-inhibitor0.6236
Distribution
Subcellular localizationLysosome0.4272
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8193
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.6793
CYP450 1A2 InhibitorNon-inhibitor0.8909
CYP450 2C9 InhibitorNon-inhibitor0.9166
CYP450 2D6 InhibitorNon-inhibitor0.9505
CYP450 2C19 InhibitorNon-inhibitor0.8370
CYP450 3A4 InhibitorNon-inhibitor0.9408
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7733
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8041
Non-inhibitor0.8442
AMES ToxicityAMES toxic0.8855
CarcinogensNon-carcinogens0.9156
Fish ToxicityHigh FHMT0.9976
Tetrahymena Pyriformis ToxicityHigh TPT0.9116
Honey Bee ToxicityLow HBT0.9052
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.8102
Carcinogenicity (Three-class)Non-required0.6109
Model Value Unit
Absorption
Aqueous solubility-3.5388LogS
Caco-2 Permeability1.2958LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0693LD50, mol/kg
Fish Toxicity1.1700pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6603pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cattle,MuscleJapan0.4ppm
Other Aquatic AnimalJapan0.3ppm
CrustaceansJapan0.3ppm
Shelled MolluscasJapan0.3ppm
Other FishJapan0.3ppm
SalmoniformesJapan0.3ppm
AnguilliformesJapan0.3ppm
PerciformesJapan0.3ppm
Other Poultry Animals,Edible OffalJapan0.6ppm
Chicken,Edible OffalJapan0.6ppm
Other Poultry Animals,KidneyJapan0.6ppm
Chicken,KidneyJapan0.6ppm
Other Poultry Animals,LiverJapan2ppm
Chicken,LiverJapan2ppm
Other Poultry Animals,FatJapan0.4ppm
Chicken,FatJapan0.4ppm
Other Poultry Animals,MuscleJapan0.3ppm
Chicken,MuscleJapan0.3ppm
Other Terrestrial Mammals,Edible OffalJapan0.8ppm
Pig,Edible OffalJapan0.02ppm

References

TitleJournalDatePubmed ID
Efficient Reduction of Antibacterial Activity and Cytotoxicity of Fluoroquinolones by Fungal-Mediated N-Oxidation.J Agric Food Chem2017 Apr 1928365994
Effect of various storage conditions on the stability of quinolones in raw milk.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016Jul27258809
Electrical field assisted matrix solid phase dispersion as a powerful tool toimprove the extraction efficiency and clean-up of fluoroquinolones in bovinemilk.J Chromatogr A2016 Aug 2627492598
Antibiotic susceptibility profiles of Mycoplasma sp. 1220 strains isolated fromgeese in Hungary.BMC Vet Res2016 Aug 1927543140
Evaluation and validation of a multi-residue method based on biochip technologyfor the simultaneous screening of six families of antibiotics in muscle andaquaculture products.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201626612266
Determination of selected veterinary antimicrobials in poultry excreta byUHPLC-MS/MS, for application in Salmonella control programs.Anal Bioanal Chem2015 Jun25633214
Determination of fluoroquinolones in chicken feces - a new liquid-liquidextraction method combined with LC-MS/MS.Environ Toxicol Pharmacol2014 Nov25305740
Comparison of different solid-phase extraction materials for the determination offluoroquinolones in chicken plasma by LC-MS/MS.J Chromatogr B Analyt Technol Biomed Life Sci2014 Mar 124566266
Identification of metabolites and thermal transformation products of quinolonesin raw cow's milk by liquid chromatography coupled to high-resolution massspectrometry.J Agric Food Chem2014 Feb 2624499328
Novel in vitro systems for prediction of veterinary drug residues in ovine milkand dairy products.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201424679113
Chemiluminescence competitive indirect enzyme immunoassay for 20 fluoroquinolone residues in fish and shrimp based on a single-chain variable fragment.Anal Bioanal Chem2013 Sep23842902
Broilers as a source of quinolone-resistant and extraintestinal pathogenic Escherichia coli in the Czech Republic.Microb Drug Resist2013 Feb23020862
Analysis of quinolone antibiotics in eggs: preparation and characterization of a raw material for method validation and quality control.Food Chem2012 Oct 125005999
Determination of (fluoro)quinolones in eggs by liquid chromatography withfluorescence detection and confirmation by liquid chromatography-tandem massspectrometry.Food Chem2012 Nov 1522868110
Determination of quinolones in milk samples using a combination of magneticsolid-phase extraction and capillary electrophoresis.Electrophoresis2012 Jul22806471
A sensitive chromatographic strip test for the rapid detection of enrofloxacin inchicken muscle.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222243423
Rapid screening method for quinolone residues in livestock and fishery productsusing immobilised metal chelate affinity chromatographic clean-up and liquidchromatography-fluorescence detection.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Sep21749230
Determination of quinolone residues in infant and young children powdered milkcombining solid-phase extraction and ultra-performance liquidchromatography-tandem mass spectrometry.J Chromatogr A2011 Oct 2121683365
Simple, stable and sensitive electrogenerated chemiluminescence detector forhigh-performance liquid chromatography and its application in directdetermination of multiple fluoroquinolone residues in milk.Talanta2011 May 1521482269
Development of a quantitative multiclass/multiresidue method for 21 veterinarydrugs in shrimp.J AOAC Int2011 Mar-Apr21563672