Stereochemical characterization of the diastereomers of the phenobarbital N-beta-D-glucose conjugate excreted in human urine.
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.
Soine
W H
WH
Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
Soine
P J
PJ
Mongrain
S E
SE
England
T M
TM
D002851:Chromatography, High Pressure Liquid; D006801:Humans; D007202:Indicators and Reagents; D008297:Male; D008618:Mephobarbital / Q000378:metabolism; D008968:Molecular Conformation; D010634:Phenobarbital / Q000031:analogs & derivatives* / Q000493:pharmacokinetics / Q000652:urine; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008618:Mephobarbital; C043855:phenobarbital-N-glucoside; D010634:Phenobarbital