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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Stereoselective inversion of (R)-(-)-benoxaprofen to the (S)-(+)-enantiomer in humans.

The enantiomeric composition of benoxaprofen [(RS)-2-(P-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid] in plasma and urine was determined after oral administration of both the racemic mixture and the (R)-(-)-enantiomer to normal human volunteers. Resolution of the diastereomeric amides, formed by the reaction of the enantiomers with (S)-(-)-apha-methylbenzylamine, was accomplished by gas chromatography. The (R)-(-1)-enantiomer of the parent drug was stereoselectively inverted to its (S)-(+) isomer in humans.[1]


  1. Stereoselective inversion of (R)-(-)-benoxaprofen to the (S)-(+)-enantiomer in humans. Bopp, R.J., Nash, J.F., Ridolfo, A.S., Shepard, E.R. Drug Metab. Dispos. (1979) [Pubmed]
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