title: Drug chirality: on the mechanism of R-aryl propionic acid class NSAIDs. Epimerization in humans and the clinical implications for the use of racemates.
abstract: This review summarizes and comments on the current understanding of both the biochemical and clinical implications of the epimerization of R-aryl propionic (APA) class (1) nonsteroidal anti-inflammatory agents (NSAIDs) to S-enantiomers in humans. This article focuses principally on rac-ibuprofen and its enantiomers. In the United States, five commercialized NSAIDs are APAs. Only two of them, rac-ibuprofen and rac-fenoprofen, are subject to significant epimerization in humans. The remaining three, rac-flurbiprofen, rac-ketoprofen, and S-naproxen, are not of interest in this context.
authors.affiliation: Department of Medicine, School of Medicine, Loma Linda University, California 92350.
authors.forename: W J
authors.initials: WJ
authors.lastname: Wechter
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D006801:Humans; D010170:Palmitoyl-CoA Hydrolase / Q000502:physiology; D011422:Propionates / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D019998:Racemases and Epimerases / Q000502:physiology; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D011422:Propionates; D010170:Palmitoyl-CoA Hydrolase; D019998:Racemases and Epimerases