Non-steroidal anti-inflammatory drugs (NSAIDs) are inhibitors of cyclooxygenase-1 (COX-1) and/or COX-2, and are widely used to treat inflammation and pain. Ketoprofen is a non-selective NSAID exhibiting IC50 values of 0.5 µM and 2.33 µM for human recombinant COX-1 and COX-2, respectively.1 It is supplied as a racemic mixture. The R-enantiomer is the more active isomer, effectively blocking COX activity without increasing inflammatory cytokine production.2
1
Barnett, J., Chow, J., Ives, D., et al. Purification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and 2 expressed in the baculovirus system. Biochim Biophys Acta1209130-139(1994).
2
Ghezzi, P., Melillo, G., Meazza, C., et al. Differential contribution of R and S isomers in ketoprofen anti-inflammatory activity: Role of cytokine modulation. J Pharmacol Exp Ther287969-974(1998).
Synonyms
2-(3-benzoylphenyl)propionic Acid
Oruvail
Orudis
Formal Name
3-benzoyl-α-methyl-benzeneacetic acid
CAS Number
22071-15-4
Molecular Formula
C16H14O3
Formula Weight
254.3
Formulation
A crystalline solid
Purity
≥98%
λmax
254 nm
Stability
2 years
Storage
-20°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
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O=C(C1=CC=CC=C1)C2=CC=CC(C(C)C(O)=O)=C2
Background Reading
Ghezzi, P., Melillo, G., Meazza, C., et al. Differential contribution of R and S isomers in ketoprofen anti-inflammatory activity: Role of cytokine modulation. J Pharmacol Exp Ther287969-974(1998).
Barnett, J., Chow, J., Ives, D., et al. Purification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and 2 expressed in the baculovirus system. Biochim Biophys Acta1209130-139(1994).
Ketoprofen is available in the following screening
library: