Oxolinic Acid

Basic Info

Common NameOxolinic Acid(F06110)
2D Structure
FRCD IDF06110
CAS Number14698-29-4
PubChem CID4628
FormulaC13H11NO5
IUPAC Name

5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid

InChI Key

KYGZCKSPAKDVKC-UHFFFAOYSA-N

InChI

InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)

Canonical SMILES

CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O

Isomeric SMILES

CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O

Synonyms
        
            Nidantin
        
            oxolinic acid
        
            14698-29-4
        
            Dioxacin
        
            Emyrenil
        
            Prodoxal
        
            Prodoxol
        
            Gramurin
        
            Oksaren
        
            Oxolinic
Classifies
                

                  
                    Veterinary Drug
                  
                    Pesticide
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 - Dihydroquinolone - Dihydroquinoline - Benzodioxole - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Pyridine - Benzenoid - Vinylogous amide - Heteroaromatic compound - Acetal - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Azacycle - Oxacycle - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen 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 Weight261.233
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Complexity446
Monoisotopic Mass261.064
Exact Mass261.064
XLogP-0.2
Formal Charge0
Heavy Atom Count19
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+0.8599
Human Intestinal AbsorptionHIA+0.9625
Caco-2 PermeabilityCaco2+0.5624
P-glycoprotein SubstrateNon-substrate0.5949
P-glycoprotein InhibitorNon-inhibitor0.8860
Non-inhibitor0.8673
Renal Organic Cation TransporterNon-inhibitor0.7231
Distribution
Subcellular localizationMitochondria0.5043
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8398
CYP450 2D6 SubstrateNon-substrate0.8155
CYP450 3A4 SubstrateNon-substrate0.6132
CYP450 1A2 InhibitorInhibitor0.9106
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9230
CYP450 2C19 InhibitorNon-inhibitor0.9007
CYP450 3A4 InhibitorNon-inhibitor0.6298
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5784
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9233
Non-inhibitor0.9106
AMES ToxicityAMES toxic0.9108
CarcinogensNon-carcinogens0.8999
Fish ToxicityHigh FHMT0.9515
Tetrahymena Pyriformis ToxicityHigh TPT0.9032
Honey Bee ToxicityLow HBT0.6701
BiodegradationNot ready biodegradable0.7961
Acute Oral ToxicityIII0.7746
Carcinogenicity (Three-class)Warning0.5191
Model Value Unit
Absorption
Aqueous solubility-3.1427LogS
Caco-2 Permeability1.0612LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6655LD50, mol/kg
Fish Toxicity0.9686pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4385pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MitsubaJapan2ppm
CeleryJapan2ppm
ParsleyJapan2ppm
ParsnipJapan0.2ppm
CarrotJapan0.2ppm
CrustaceansJapan0.03ppm
Other FishJapan0.03ppm
PerciformesJapan0.05ppm
AnguilliformesJapan0.05ppm
SalmoniformesJapan0.05ppm
Other Poultry,EggsJapan0.05ppm
Chicken,EggsJapan0.05ppm
Chicken,Edible OffalJapan1ppm
Chicken,KidneyJapan1ppm
Chicken,LiverJapan1ppm
Chicken,FatJapan0.1ppm
Chicken,MuscleJapan1ppm
Pig,Edible OffalJapan1ppm
Cattle,Edible OffalJapan1ppm
Pig,KidneyJapan1ppm

References

TitleJournalDatePubmed ID
A pharmaco-epidemiological study of antibacterial treatments and bacterialdiseases in Norwegian aquaculture from 2011 to 2016.Dis Aquat Organ2018 May 729733026
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
Sucralose Increases Antimicrobial Resistance and Stimulates Recovery ofEscherichia coli Mutants.Curr Microbiol2017 Jul28424940
Validation of a procedure to quantify oxolinic acid, danofloxacin, ciprofloxacin and enrofloxacin in selected meats by micellar liquid chromatography according toEU Commission Decision 2002/657/EC.Electrophoresis2017 Aug28597925
Determination of oxolinic acid, danofloxacin, ciprofloxacin, and enrofloxacin in porcine and bovine meat by micellar liquid chromatography with fluorescencedetection.Food Chem2017 Apr 1527979089
Environmental impact assessment of veterinary drug on fish aquaculture for foodsafety.Drug Test Anal2016 May27443211
Resveratrol Antagonizes Antimicrobial Lethality and Stimulates Recovery ofBacterial Mutants.PLoS One2016 Apr 527045517
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
Analysis of quinolone antibiotics in eggs: preparation and characterization of a raw material for method validation and quality control.Food Chem2012 Oct 125005999
Quality control ranges for testing broth microdilution susceptibility ofFlavobacterium columnare and F. psychrophilum to nine antimicrobials.Dis Aquat Organ2012 Nov 1923324417
Determination of (fluoro)quinolones in eggs by liquid chromatography withfluorescence detection and confirmation by liquid chromatography-tandem massspectrometry.Food Chem2012 Nov 1522868110
Laser diode thermal desorption mass spectrometry for the analysis of quinoloneantibiotic residues in aquacultured seafood.Rapid Commun Mass Spectrom2012 Dec 3023136016
DNA gyrase and topoisomerase IV mutations in quinolone-resistant Flavobacteriumpsychrophilum isolated from diseased salmonids in Norway.Microb Drug Resist2012 Apr22283604
Use of antibiotics in plant agriculture.Rev Sci Tech2012 Apr22849276
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
Prevalence and antimicrobial resistance of Listeria monocytogenes isolated inchicken slaughterhouses in Northern Greece.J Food Prot2011 Jun21669084