title: LC determination of the diastereomers of 1-(beta-D-glucopyranosyl)phenobarbital in human urine.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
authors.forename: W H
authors.initials: WH
authors.lastname: Soine
authors.forename: P J
authors.initials: PJ
authors.lastname: Soine
authors.forename: T M
authors.initials: TM
authors.lastname: England
authors.forename: D F
authors.initials: DF
authors.lastname: Welty
authors.forename: J H
authors.initials: JH
authors.lastname: Wood
mesh_terms: D044466:Asian People; D002853:Chromatography, Liquid / Q000379:methods; D006801:Humans; D010634:Phenobarbital / Q000031:analogs & derivatives* / Q000493:pharmacokinetics / Q000652:urine; D013237:Stereoisomerism; D044465:White People
chemical_list: C017414:4-hydroxyphenobarbital; C043855:phenobarbital-N-glucoside; D010634:Phenobarbital