Basic Info

Common NameKetoprofen(F05961)
2D Structure
FRCD IDF05961
CAS Number22071-15-4
PubChem CID3825
FormulaC16H14O3
IUPAC Name

2-(3-benzoylphenyl)propanoic acid

InChI Key

DKYWVDODHFEZIM-UHFFFAOYSA-N

InChI

InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

Canonical SMILES

CC(C1=CC=CC(=C1)C(=O)C2=CC=CC=C2)C(=O)O

Isomeric SMILES

CC(C1=CC=CC(=C1)C(=O)C2=CC=CC=C2)C(=O)O

Synonyms
        
            2-(3-Benzoylphenyl)propanoic acid
        
            ketoprofen
        
            22071-15-4
        
            Orudis
        
            2-(3-Benzoylphenyl)propionic acid
        
            m-Benzoylhydratropic acid
        
            Ketoprofene
        
            Profenid
        
            Oruvail
        
            3-Benzoylhydratropic acid
        
Classifies
                

                  
                    Predicted: Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzophenones
Intermediate Tree NodesNot available
Direct ParentBenzophenones
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzophenone - Aryl-phenylketone - Diphenylmethane - 2-phenylpropanoic-acid - Benzoyl - Aryl ketone - Ketone - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Properties

Property NameProperty Value
Molecular Weight254.285
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity331
Monoisotopic Mass254.094
Exact Mass254.094
XLogP3.1
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+0.9382
Human Intestinal AbsorptionHIA+0.9928
Caco-2 PermeabilityCaco2+0.8866
P-glycoprotein SubstrateNon-substrate0.7132
P-glycoprotein InhibitorNon-inhibitor0.9168
Non-inhibitor0.9589
Renal Organic Cation TransporterNon-inhibitor0.8818
Distribution
Subcellular localizationMitochondria0.9091
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7183
CYP450 2D6 SubstrateNon-substrate0.9598
CYP450 3A4 SubstrateNon-substrate0.7685
CYP450 1A2 InhibitorNon-inhibitor0.9046
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9604
CYP450 2C19 InhibitorNon-inhibitor0.9465
CYP450 3A4 InhibitorNon-inhibitor0.9598
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9438
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9661
Non-inhibitor0.9595
AMES ToxicityNon AMES toxic0.9801
CarcinogensNon-carcinogens0.6299
Fish ToxicityHigh FHMT0.8881
Tetrahymena Pyriformis ToxicityHigh TPT0.8767
Honey Bee ToxicityHigh HBT0.6266
BiodegradationReady biodegradable0.6701
Acute Oral ToxicityII0.7719
Carcinogenicity (Three-class)Non-required0.7238

Model Value Unit
Absorption
Aqueous solubility-3.6373LogS
Caco-2 Permeability1.1678LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2378LD50, mol/kg
Fish Toxicity1.4416pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8179pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cattle,KidneyJapan0.05ppm
MilkJapan0.05ppm
Cattle,Edible OffalJapan0.05ppm
Cattle,LiverJapan0.05ppm
Cattle,FatJapan0.05ppm
Cattle,MuscleJapan0.05ppm

References

TitleJournalDatePubmed ID
Pharmaceutical grey water footprint: Accounting, influence of wastewatertreatment plants and implications of the reuse.Water Res2018 May 1529482095
Postpartum ketoprofen treatment does not alter stress biomarkers in cows andcalves experiencing assisted and unassisted parturition: a randomised controlled trial.Vet Rec2018 Jun 3029960984
Periparturient Behavior and Physiology: Further Insight Into the FarrowingProcess for Primiparous and Multiparous Sows.Front Vet Sci2018 Jun 1229946552
Removal of emerging organic contaminants in a poplar vegetation filter.J Hazard Mater2018 Jan 1528866407
Photostability testing using online reactor HPLC hyphenation and mass spectrometric compound identification illustrated by ketoprofen as model compound.J Pharm Biomed Anal2017 Oct 2528732306
Sorption and desorption of selected non-steroidal anti-inflammatory drugs in anagricultural loam-textured soil.Chemosphere2017 May28199939
Non-steroidal anti-inflammatory drugs in the watercourses of Elbe basin in Czech Republic.Chemosphere2017 Mar28011407
Phytochemicals enhance antioxidant enzyme expression to protect against NSAID-induced oxidative damage of the gastrointestinal mucosa.Mol Nutr Food Res2017 Jun27883262
Distribution of Animal Drugs among Curd, Whey, and Milk Protein Fractions inSpiked Skim Milk and Whey.J Agric Food Chem2017 Feb 128052193
Characterization and biological properties of copper(II)-ketoprofen complexes.J Inorg Biochem2016 Sep27323214
Ketoprofen and antinociception in hypo-oestrogenic Wistar rats fed on a highsucrose diet.Eur J Pharmacol2016 Oct 527339452
Distribution of Animal Drugs between Skim Milk and Milk Fat Fractions in SpikedWhole Milk: Understanding the Potential Impact on Commercial Milk Products.J Agric Food Chem2016 Jan 1326652058
Simultaneous attenuation of pharmaceuticals, organic matter, and nutrients inwastewater effluent through managed aquifer recharge: Batch and column studies.Chemosphere2016 Jan26559901
Formulation and in vitro evaluation of ketoprofen fast-dissolving tablets.Pharm Dev Technol2016 Dec25798913
Application of a hybrid ordered mesoporous silica as sorbent for solid-phasemulti-residue extraction of veterinary drugs in meat by ultra-high-performanceliquid chromatography coupled to ion-trap tandem mass spectrometry.J Chromatogr A2016 Aug 1227412322
Pomegranate seed oil nanoemulsions improve the photostability and in vivo antinociceptive effect of a non-steroidal anti-inflammatory drug.Colloids Surf B Biointerfaces2016 Aug 127088191
Diets with no or low amounts of dietary fiber can reduce small intestinal ulcers induced by non-steroidal anti-inflammatory drugs in dogs.J Physiol Pharmacol2016 Aug27779477
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
Using chemical benchmarking to determine the persistence of chemicals in aSwedish lake.Environ Sci Technol2015 Feb 325565241
Thermoresponsive ketoprofen-imprinted monolith prepared in ionic liquid.Anal Bioanal Chem2014 Sep24916075