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. 1989 Aug;28(2):151–154. doi: 10.1111/j.1365-2125.1989.tb05407.x

Stereoselectivity in the urinary excretion of the mercapturates of (R-) and (S-) alpha-bromoisovalerylurea in man.

J M te Koppele 1, C Schipper 1, D D Breimer 1, G J Mulder 1
PMCID: PMC1379896  PMID: 2775620

Abstract

1. alpha-Bromoisovalerylurea (BIU) is a racemic drug that is metabolized by glutathione conjugation. The urinary excretion of the separate diastereomeric mercapturates formed from (S)- and (R)-BIU in healthy young human volunteers was investigated. 2. A pronounced stereoselectivity was observed: the mercapturate formed from R-BIU was excreted with a t1/2 of 1.5 +/- 0.4 h, while that from S-BIU showed a t1/2 of 3.1 +/- 1.3 h. Moreover, 22.5 +/- 4.3 and 5.7 +/- 1.6% of the dose, respectively, was excreted as each mercapturate diastereomer in 24 h. 3. This is the first example of stereoselectivity in the elimination of a substrate for glutathione conjugation in man.

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Selected References

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