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Bi‐directional chiral inversion of ketoprofen in CD‐1 mice
Author(s) -
Jamali Fakhreddin,
Lovlin Ray,
Aberg Gunnar
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:1<29::aid-chir6>3.0.co;2-b
Subject(s) - chemistry , ketoprofen , inversion (geology) , chirality (physics) , stereochemistry , chromatography , chiral perturbation theory , quantum mechanics , physics , nambu–jona lasinio model , paleontology , pion , structural basin , biology
The R enantiomers of some of the 2‐arylpropionic acid non‐steroidal antiinflammatory drugs (NSAIDs) are known to undergo metabolic chiral inversion to their more pharmacologically active antipodes. This process is drug and species dependent and usually unidirectional. The S to R chiral inversion, on the other hand, is rare and has been observed, in substantial extents, only for ibuprofen in guinea pigs and 2‐phenylpropionic acid in dogs. After i.p. administration of single doses of racemic ketoprofen or its optically pure enantiomers to male CD‐1 mice and subsequent study of the concentration time‐course of the enantiomers, we noticed substantial chiral inversion in both directions. Following racemic doses, no stereoselectivity in the plasma‐concentration time courses was observed. After dosing with optically pure enantiomer, the concentration of the administered enantiomer predominated during the absorption phase. During the terminal elimination phase, however, the enantiomers had the same concentrations. Our observation is suggestive of a rapid and reversible chiral inversion for ketoprofen enantiomers in mice. Chirality 9:29–31, 1997. © 1997 Wiley‐Liss, Inc.