Stereoselective Inversion of (R)-Fenoprofen to (S)-Fenoprofen in Humans

doi:10.1002/jps.2600740122

Journal of Pharmaceutical Sciences

Volume 74, Issue 1, January 1985, Pages 82-84

https://doi.org/10.1002/jps.2600740122 Get rights and content

Abstract

The concentrations of the (R)- and (S)-enantiomers of fenoprofen (α-methyl-3-phenoxy-benzeneacetic acid) were measured in plasma and urine of volunteers after oral administration of the (R,S)-racemate. In addition, urinary concentrations of the (R)- and (S)-4′-hydroxy metabolite of fenoprofen, the major metabolite, were measured. The (R)-enantiomer of fenoprofen was stereoselectively inverted to (S)-fenoprofen, which was the major isomeric form found in plasma and urine. A potency comparison of the enantiomers in vitro showed the (S)-isomer to be 35 times more active than the (R)-isomer in inhibiting the fatty acid cyclo-oxygenase pathway from human platelets. In vivo, the similar pharmacological potency of the two enantiomers previously observed in experimental animals may have been due to the rapid inversion of the (R)-to (S)-isomer.

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NotesStereoselective Inversion of (R)-Fenoprofen to (S)-Fenoprofen in Humans

Abstract

J. Pharm. Sci.

J. Pharm. Sci.

J. Pharm. Sci.

Biochem. Biophys. Res. Commun.

Drug Metab. Dispos.

Drug Metab. Dispos.

Drug Metab. Dispos.

Notes
Stereoselective Inversion of (R)-Fenoprofen to (S)-Fenoprofen in Humans