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. 1990 Apr;7(4):402-6.
doi: 10.1023/a:1015831725205.

Stereochemical characterization of the diastereomers of the phenobarbital N-beta-D-glucose conjugate excreted in human urine

W H Soine  1 , P J Soine, S E Mongrain, T M England
Affiliations

Stereochemical characterization of the diastereomers of the phenobarbital N-beta-D-glucose conjugate excreted in human urine

W H Soine et al. Pharm Res. 1990 Apr.

Abstract

The absolute configuration of the N-beta-D-glucoside metabolites of phenobarbital was determined by methylation of the diastereomers to make mephobarbital N-beta-D-glucosides, followed by oxidative removal of glucose to give the optical isomers of mephobarbital. Following a single oral dose of phenobarbital to two male subjects, both phenobarbital N-beta-D-glucosides were excreted in the urine. The absolute configuration (C-5 position) of the major phenobarbital N-beta-D-glucoside excreted in the urine was the S form. A pronounced stereoselective formation and/or urinary excretion occurs for the N-glucoside conjugates of phenobarbital in humans.

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