Danofloxacin

Basic Info

Common NameDanofloxacin(F05771)
2D Structure
FRCD IDF05771
CAS Number112398-08-0
PubChem CID71335
FormulaC19H20FN3O3
IUPAC Name

1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-4-oxoquinoline-3-carboxylic acid

InChI Key

QMLVECGLEOSESV-RYUDHWBXSA-N

InChI

InChI=1S/C19H20FN3O3/c1-21-7-12-4-11(21)8-22(12)17-6-16-13(5-15(17)20)18(24)14(19(25)26)9-23(16)10-2-3-10/h5-6,9-12H,2-4,7-8H2,1H3,(H,25,26)/t11-,12-/m0/s1

Canonical SMILES

CN1CC2CC1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F

Isomeric SMILES

CN1C[C@@H]2C[C@H]1CN2C3=C(C=C4C(=C3)N(C=C(C4=O)C(=O)O)C5CC5)F

Synonyms
        
            NCGC00164548-01
        
            Danofloxacin
        
            112398-08-0
        
            Danofloxacine
        
            Danofloxacino
        
            Danofloxacinum
        
            UNII-24CU1YS91D
        
            24CU1YS91D
        
            C19H20FN3O3
        
            DSSTox_CID_26432
Classifies
                

                  
                    Predicted: 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 - N-arylpiperazine - Aminoquinoline - Haloquinoline - Dihydroquinolone - Dihydroquinoline - Pyridine carboxylic acid or derivatives - Pyridine carboxylic acid - Tertiary aliphatic/aromatic amine - Dialkylarylamine - N-methylpiperazine - N-alkylpiperazine - Piperazine - Aryl halide - Aryl fluoride - 1,4-diazinane - Pyridine - N-alkylpyrrolidine - Benzenoid - Heteroaromatic compound - Vinylogous amide - Pyrrolidine - Amino acid or derivatives - Tertiary amine - Tertiary aliphatic amine - Amino acid - Azacycle - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Hydrocarbon derivative - Amine - Organic oxide - Organohalogen compound - Organofluoride - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - 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 Weight357.385
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Complexity679
Monoisotopic Mass357.149
Exact Mass357.149
XLogP-0.3
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count2
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-0.9041
Human Intestinal AbsorptionHIA+0.9957
Caco-2 PermeabilityCaco2+0.8346
P-glycoprotein SubstrateSubstrate0.7522
P-glycoprotein InhibitorNon-inhibitor0.9017
Non-inhibitor0.8313
Renal Organic Cation TransporterNon-inhibitor0.6180
Distribution
Subcellular localizationLysosome0.5035
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7999
CYP450 2D6 SubstrateNon-substrate0.8480
CYP450 3A4 SubstrateNon-substrate0.5895
CYP450 1A2 InhibitorNon-inhibitor0.8330
CYP450 2C9 InhibitorNon-inhibitor0.8611
CYP450 2D6 InhibitorNon-inhibitor0.8814
CYP450 2C19 InhibitorNon-inhibitor0.7717
CYP450 3A4 InhibitorNon-inhibitor0.8609
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7240
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8819
Non-inhibitor0.8685
AMES ToxicityAMES toxic0.7906
CarcinogensNon-carcinogens0.8923
Fish ToxicityHigh FHMT0.9991
Tetrahymena Pyriformis ToxicityHigh TPT0.9293
Honey Bee ToxicityLow HBT0.8852
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7524
Carcinogenicity (Three-class)Non-required0.5795
Model Value Unit
Absorption
Aqueous solubility-3.3284LogS
Caco-2 Permeability1.5047LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2811LD50, mol/kg
Fish Toxicity1.0194pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6698pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle Of CattleUnited States0.2ppm
Liver Of CattleUnited States0.2ppm
Other Aquatic AnimalJapan0.1ppm
CrustaceansJapan0.1ppm
Shelled MolluscasJapan0.1ppm
Other FishJapan0.1ppm
PerciformesJapan0.1ppm
AnguilliformesJapan0.1ppm
SalmoniformesJapan0.1ppm
Other Poultry Animals,Edible OffalJapan0.4ppm
Chicken,Edible OffalJapan0.4ppm
Other Poultry Animals,KidneyJapan0.4ppm
Other Poultry Animals,LiverJapan0.4ppm
Other Poultry Animals,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.2ppm
MilkJapan0.05ppm
Other Terrestrial Mammals,Edible OffalJapan0.4ppm
Pig,Edible OffalJapan0.05ppm
Cattle,Edible OffalJapan0.4ppm
Other Terrestrial Mammals,KidneyJapan0.4ppm

References

TitleJournalDatePubmed ID
Hexafluoroisopropanol-induced salt-free catanionic surfactant coacervateextraction method for determination of fluoroquinolones in milk samples.Food Chem2018 Mar 129037667
Flaxseed-enriched diets change milk concentration of the antimicrobialdanofloxacin in sheep.BMC Vet Res2018 Jan 1529334949
Pharmacokinetics and distribution in interstitial and pulmonary epithelial liningfluid of danofloxacin in ruminant and preruminant calves.J Vet Pharmacol Ther2017 Apr27476495
Effect of various storage conditions on the stability of quinolones in raw milk.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016Jul27258809
Microbial screening for quinolones residues in cow milk by bio-optical method.J Pharm Biomed Anal2015 Mar 1525555518
Luminescent determination of quinolones in milk samples by liquidchromatography/post-column derivatization with terbium oxide nanoparticles.J Chromatogr A2015 Jul 3126077970
Short communication: The gain-of-function Y581S polymorphism of the ABCG2transporter increases secretion into milk of danofloxacin at the therapeutic dosefor mastitis treatment.J Dairy Sci2015 Jan25465626
Fabrication of enrofloxacin imprinted organic-inorganic hybrid mesoporous sorbentfrom nanomagnetic polyhedral oligomeric silsesquioxanes for the selectiveextraction of fluoroquinolones in milk samples.J Chromatogr A2014 Sep 2625171943
In vitro selection of RNA aptamers that selectively bind danofloxacin.Biochem Biophys Res Commun2014 Jun 1324792181
Development of a novel genetically modified bioluminescent-bacteria-based assayfor detection of fluoroquinolones in animal-derived foods.Anal Bioanal Chem2014 Dec25354889
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
Effects of triclabendazole on secretion of danofloxacin and moxidectin into themilk of sheep: role of triclabendazole metabolites as inhibitors of the ruminant ABCG2 transporter.Vet J2013 Nov23981352
Inhibition of ABCG2/BCRP transporter by soy isoflavones genistein and daidzein:effect on plasma and milk levels of danofloxacin in sheep.Vet J2013 May23083838
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
The bovine ATP-binding cassette transporter ABCG2 Tyr581Ser single-nucleotidepolymorphism increases milk secretion of the fluoroquinolone danofloxacin.Drug Metab Dispos2013 Mar23230133
Terbium-sensitised luminescence screening method for fluoroquinolones in beefserum.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201323472630
Production of the broad specific monoclonal antibody against sarafloxacin forrapid immunoscreening of 12 fluoroquinolones in meat.J Environ Sci Health B201323305282
Highly sensitive synchronous fluorescence measurement of danofloxacin inpharmaceutical and milk samples using aluminium (III) enhanced fluorescence.J Fluoresc2012 Sep22730138
Analysis of quinolone antibiotics in eggs: preparation and characterization of a raw material for method validation and quality control.Food Chem2012 Oct 125005999