Soine W H, Soine P J, Mongrain S E, England T M
Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Richmond 23298-0581.
Pharm Res. 1990 Apr;7(4):402-6. doi: 10.1023/a:1015831725205.
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.
通过将非对映异构体甲基化制成美沙比妥N-β-D-葡糖苷，随后氧化去除葡萄糖以得到美沙比妥的光学异构体，确定了苯巴比妥N-β-D-葡糖苷代谢物的绝对构型。给两名男性受试者单次口服苯巴比妥后，两种苯巴比妥N-β-D-葡糖苷均从尿液中排出。尿液中排出的主要苯巴比妥N-β-D-葡糖苷的绝对构型（C-5位）为S型。在人体中，苯巴比妥的N-葡糖苷共轭物存在明显的立体选择性形成和/或尿液排泄现象。
