(S)-Ketoprofen

Ketoprofen (Item No. 10006661) is a non-selective, non-steroidal, anti-inflammatory drug exhibiting IC₅₀ values of 0.5 and 2.33 µM for human recombinant COX-1 and COX-2 (Item No. 60122), respectively.¹ Ketoprofen is commonly used in vivo as a racemic mixture of (R)- and (S)-enantiomers. (S)-Ketoprofen is a potent inhibitor of COX-1 and COX-2 (IC₅₀s = 1.9 and 27 nM, respectively), whereas the (R)-enantiomer is 100 to 1,000 times less potent.^2,3 Notably, (S)-ketoprofen is known to be formed from the (R)-enantiomer in several animal species, except in humans and guinea pigs.³ Also, the pharmacokinetics of ketoprofen enantiomers and their glucuronide metabolites are altered in humans with rheumatoid arthritis or renal disease.^4,5

WARNING This product is not for human or veterinary use.

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. Acta 1209(1), 130-139 (1994).

2. Palomer, A., Pérez, J.J., Navea, S., et al. Modeling cyclooxygenase inhibition. Implication of active site hydration on the selectivity of ketoprofen analogues. J. Med. Chem. 43(11), 2280-2284 (2000).

3. 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. Ther. 287(3), 969-974 (1998).

4. Glówka, F., Karazniewicz-Lada, M., Grzeskowiak, E., et al. Clinical pharmacokinetics of ketoprofen enantiomers in wild type of Cyp 2c8 and Cyp 2c9 patients with rheumatoid arthritis. Eur. J. Drug Metab. Pharmacokinet. 36(3), 167-173 (2011).

5. Grubb, N.G., Rudy, D.W., Brater, D.C., et al. Stereoselective pharmacokinetics of ketoprofen and ketoprofen glucuronide in end-stage renal disease: Evidence for a 'futile cycle' of elimination. Br. J. Clin. Pharmacol. 48(4), 494-500 (1999).