ketoprofen   Click here for help

GtoPdb Ligand ID: 4795

Synonyms: Actron® | Orudis®
Approved drug Immunopharmacology Ligand
ketoprofen is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: The approved drug ketoprofen is a mixture of two stereoisomers; an (R)-enantiomer (see PubChem CID 180540), and an (S)-enantiomer (see PubChem CID 667550), with only the (S)-enantiomer possessing biological activity. The structure shown here does not specify stereochemistry and represents the mixture of isomers.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 54.37
Molecular weight 254.09
XLogP 3.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)C
Isomeric SMILES OC(=O)C(c1cccc(c1)C(=O)c1ccccc1)C
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)
InChI Key DKYWVDODHFEZIM-UHFFFAOYSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
COX-1 Primary target of this compound Hs Inhibitor Inhibition 6.5 pIC50 - 1
pIC50 6.5 (IC50 3.3x10-7 M) [1]
Description: Inhibition of COX1 in human whole blood.
COX-2 Primary target of this compound Hs Inhibitor Inhibition 6.2 pIC50 - 1
pIC50 6.2 (IC50 6.9x10-7 M) [1]
Description: Inhibition of COX2 in human whole blood.
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
SMCT1 Hs Inhibitor Inhibition 3.9 pIC50 - 2
pIC50 3.9 (IC50 1.19x10-4 M) [2]
Ligand mentioned in the following text fields