Carprofen

Basic Info

Common NameCarprofen(F05661)
2D Structure
FRCD IDF05661
CAS Number53716-49-7
PubChem CID2581
FormulaC15H12ClNO2
IUPAC Name

2-(6-chloro-9H-carbazol-2-yl)propanoic acid

InChI Key

PUXBGTOOZJQSKH-UHFFFAOYSA-N

InChI

InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)

Canonical SMILES

CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O

Isomeric SMILES

CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O

Synonyms
        
            Rimadyl
        
            Carprofene [INN-French]
        
            carprofen
        
            53716-49-7
        
            2-(6-Chloro-9H-carbazol-2-yl)propanoic acid
        
            Imadyl
        
            Ridamyl
        
            Carprofene
        
            Carprofeno
        
            Carprofenum
Classifies
                

                  
                    Predicted: Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassIndoles and derivatives
SubclassCarbazoles
Intermediate Tree NodesNot available
Direct ParentCarbazoles
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsCarbazole - Indole - Aryl chloride - Aryl halide - Benzenoid - Pyrrole - Heteroaromatic compound - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Organochloride - Organohalogen compound - Organic oxygen compound - Organic oxide - Organic nitrogen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Properties

Property NameProperty Value
Molecular Weight273.716
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Complexity362
Monoisotopic Mass273.056
Exact Mass273.056
XLogP4
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+0.9742
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5595
P-glycoprotein SubstrateNon-substrate0.7062
P-glycoprotein InhibitorNon-inhibitor0.9850
Non-inhibitor0.9319
Renal Organic Cation TransporterNon-inhibitor0.8485
Distribution
Subcellular localizationMitochondria0.4735
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7405
CYP450 2D6 SubstrateNon-substrate0.8318
CYP450 3A4 SubstrateNon-substrate0.6389
CYP450 1A2 InhibitorInhibitor0.6573
CYP450 2C9 InhibitorNon-inhibitor0.7193
CYP450 2D6 InhibitorNon-inhibitor0.9481
CYP450 2C19 InhibitorNon-inhibitor0.7037
CYP450 3A4 InhibitorNon-inhibitor0.8308
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7940
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9725
Non-inhibitor0.8697
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.8521
Fish ToxicityHigh FHMT0.9695
Tetrahymena Pyriformis ToxicityHigh TPT0.9490
Honey Bee ToxicityLow HBT0.5577
BiodegradationNot ready biodegradable0.9874
Acute Oral ToxicityII0.7358
Carcinogenicity (Three-class)Non-required0.5366
Model Value Unit
Absorption
Aqueous solubility-4.4286LogS
Caco-2 Permeability1.0471LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.4155LD50, mol/kg
Fish Toxicity0.8693pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3069pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Terrestrial Mammals,Edible OffalJapan1ppm
Cattle,Edible OffalJapan1ppm
Other Terrestrial Mammals,KidneyJapan1ppm
Cattle,KidneyJapan1ppm
Other Terrestrial Mammals,LiverJapan1ppm
Cattle,LiverJapan1ppm
Other Terrestrial Mammals,FatJapan1ppm
Cattle,FatJapan1ppm
Other Terrestrial Mammals,MuscleJapan0.5ppm
Cattle,MuscleJapan0.5ppm

References

TitleJournalDatePubmed ID
The use of toxicokinetics and exposure studies to show that carprofen in cattle tissue could lead to secondary toxicity and death in wild vultures.Chemosphere2018 Jan28985539
Sterility and Stability of Diluted Carprofen in a Multidose Vial in theLaboratory Animal Setting.J Am Assoc Lab Anim Sci2017 May 128535864
Effect of sorbitol, single, and multidose activated charcoal administration oncarprofen absorption following experimental overdose in dogs.J Vet Emerg Crit Care (San Antonio)2015 Sep-Oct25891141
A multiresidue liquid chromatographic/tandem mass spectrometric method for thedetection and quantitation of 15 nonsteroidal anti-inflammatory drugs (NSAIDs) inbovine meat and milk.Anal Bioanal Chem2015 Jun25814273
Pharmacological effects of a C-phycocyanin-based multicomponent nutraceutical in an in-vitro canine chondrocyte model of osteoarthritis.Can J Vet Res2015 Jul26130858
Randomised trial of the bioavailability and efficacy of orally administeredflunixin, carprofen and ketoprofen in a pain model in sheep.Aust Vet J2015 Aug26220318
Short communication: Effects of analgesic use postcalving on cow welfare andproduction.J Dairy Sci2014 Feb24290817
Determination of non-steroidal anti-inflammatory drugs and their metabolites inmilk by liquid chromatography-tandem mass spectrometry.Anal Bioanal Chem2012 Jul22395450
Assessment of carprofen and buprenorphine on recovery of mice after surgicalremoval of the mammary fat pad.J Am Assoc Lab Anim Sci2010 Sep20858363
Confirmatory analysis of non-steroidal anti-inflammatory drugs in bovine milk by high-performance liquid chromatography with fluorescence detection.J Chromatogr A2010 Apr 2320227702
Systematic review of the management of canine osteoarthritis.Vet Rec2009 Apr 419346540
Effect of carprofen treatment following experimentally induced Escherichia colimastitis in primiparous cows.J Dairy Sci2005 Jul15956299
Protective effect of the chondroprotective agent Cosequin DS on bovine articular cartilage exposed in vitro to nonsteroidal antiinflammatory agents.Vet Ther2002 Summer19750743
Assessment of the postoperative discomfort of intra-auricularly hypophysectomizedrats.Lab Anim2002 Apr11943078
Effects of butorphanol and carprofen on the minimal alveolar concentration ofisoflurane in dogs.J Am Vet Med Assoc2000 Oct 111019709
Pharmacodynamics and pharmacokinetics of carprofen, a non-steroidal anti-inflammatory drug, in healthy cows and cows with Escherichia coli endotoxin-induced mastitis.J Vet Pharmacol Ther1991 Sep1744930