LC determination of the diastereomers of 1-(beta-D-glucopyranosyl)phenobarbital in human urine.
The "product enantioselectivity" associated with the urinary excretion of the phenobarbital N-glucoside conjugates has not been determined previously. A liquid chromatography method using gradient elution was developed for quantifying both phenobarbital N-glucoside conjugates, phenobarbital, and p-hydroxyphenobarbital. Following a single oral dose of phenobarbital to male Caucasian and Oriental subjects, both phenobarbital N-glucoside conjugates were observed in the urine. In seven subjects, 3.3-10.6% of the phenobarbital dose was detected as a single phenobarbital N-glucoside (S configuration at the C-5 position of the barbiturate ring). The other phenobarbital N-glucoside diastereomer accounted for less than 1.5% of the phenobarbital dose. The urinary excretion of the major phenobarbital N-glucoside diastereomer paralleled the urinary excretion of phenobarbital and was comparable in both Caucasian and Oriental subjects. These results indicate a pronounced selectivity for the formation and/or urinary excretion of the phenobarbital N-glucosides.
Soine
W H
WH
Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
Soine
P J
PJ
England
T M
TM
Welty
D F
DF
Wood
J H
JH
D044466:Asian People; D002853:Chromatography, Liquid / Q000379:methods; D006801:Humans; D010634:Phenobarbital / Q000031:analogs & derivatives* / Q000493:pharmacokinetics / Q000652:urine; D013237:Stereoisomerism; D044465:White People
C017414:4-hydroxyphenobarbital; C043855:phenobarbital-N-glucoside; D010634:Phenobarbital