CARPROFEN

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Search structure


Trade Names	RIMADYL
Synonyms	Carprofen Carprofen for veterinary use NSC-297935 RO 20-5720/000 Rimadyl Ro-205720000
Status
Molecule Category	UNKNOWN
UNII	FFL0D546HO
EPA CompTox	DTXSID1045871


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	PUXBGTOOZJQSKH-UHFFFAOYSA-N
Smiles	CC(C(=O)O)c1ccc2c(c1)[nH]c1ccc(Cl)cc12
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C15H12ClNO2
Molecular Weight	273.72
AlogP	4.16
Hydrogen Bond Acceptor	1.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	2.0
Polar Surface Area	53.09
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	19.0

Bioactivity

Mechanism of Action	Action	Reference
Cyclooxygenase-2 inhibitor	INHIBITOR	DailyMed


Protein: Cyclooxygenase-2 Description: Prostaglandin G/H synthase 2 Organism : Homo sapiens P35354 ENSG00000073756

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	32000-78600	-	-	-
Enzyme Oxidoreductase	-	100-38000	-	-	-
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor	-	-	-	-	5
Secreted protein	-	-	580	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	48
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	3000	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibitory activity against cell-free canine COX-2	Canis lupus familiaris	102.0 nM
Inhibition of lipopolysaccharide-induced PGE-2 production at 10e-5 M	Mus musculus	99.0 %
Inhibition of CXCL8-induced chemotaxis of human polymorphonuclear cells at 10e-8 M	Homo sapiens	5.0 %
Antiproliferative activity against human PC3 cells at 100 uM after 72 hrs by MTT assay	Homo sapiens	5.0 %
Inhibition of human recombinant COX2 after 5 mins	Homo sapiens	100.0 nM
Inhibition of human recombinant COX-2 assessed as residual activity by measuring formation of 12-HHT from arachidonic acid by HPLC analysis	Homo sapiens	102.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	47.72 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	77.78 %
Binding affinity to human C5a assessed as dissociation constant after 1 hr by circular dichroism analysis	Homo sapiens	580.0 nM

Cross References

Resources	Reference
ChEBI	364453
ChEMBL	CHEMBL1316
DrugBank	DB00821
DrugCentral	518
FDA SRS	FFL0D546HO
Human Metabolome Database	HMDB0014959
Guide to Pharmacology	7141
KEGG	C18364
PharmGKB	PA164781361
PubChem	2581
SureChEMBL	SCHEMBL3909
ZINC	ZINC01869694

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).