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人尿中排泄的异戊巴比妥N-葡萄糖苷非对映体的立体化学特征。

Stereochemical characterization of the diastereomers of the amobarbital N-glucosides excreted in human urine.

作者信息

Soine W H, Soine P J, Wireko F C, Abraham D J

机构信息

Department of Medicinal Chemistry, Virginia Commonwealth University, Richmond 23298-0581.

出版信息

Pharm Res. 1990 Aug;7(8):794-800. doi: 10.1023/a:1015900629690.

Abstract

The stereochemistry associated with the amobarbital N-glucoside diastereomers (1a and 1b) that are excreted by humans in urine is unknown. Using X-ray crystallography, the absolute configuration of 1b was determined to be S (C-5 position of the barbiturate ring). Following oral administration of amobarbital to Caucasians and Orientals, from 5 to 25% of the dose of amobarbital was excreted in the urine as 1b. The other diastereomer, 1a, accounted for less than 0.1 to 0.2% of the dose in four individuals, with none detected in nine individuals. The rate constants, kf,1b, determined from the urinary excretion of 1b were lower than those previously reported for unresolved amobarbital N-glucosides. However, based on the urinary excretion of 1b, the rate constants, K, for elimination of amobarbital in Caucasians and Orientals were similar to those previously determined from the serum levels of amobarbital and the urinary excretion of unresolved amobarbital N-glucosides. In previous studies of the N-glucosylation of amobarbital, it is likely that a single N-glucose diastereomer, 1b, was being observed.

摘要

人类尿液中排泄的异戊巴比妥N-葡萄糖苷非对映异构体(1a和1b)的立体化学尚不清楚。通过X射线晶体学,确定1b的绝对构型为S(巴比妥酸环的C-5位)。在白种人和东方人中口服异戊巴比妥后,5%至25%的异戊巴比妥剂量以1b的形式从尿液中排泄。另一种非对映异构体1a在4名个体中占剂量的不到0.1%至0.2%,在9名个体中未检测到。从1b的尿排泄测定的速率常数kf,1b低于先前报道的未解析的异戊巴比妥N-葡萄糖苷的速率常数。然而,基于1b的尿排泄,白种人和东方人中异戊巴比妥消除的速率常数K与先前从异戊巴比妥血清水平和未解析的异戊巴比妥N-葡萄糖苷的尿排泄中确定的速率常数相似。在先前关于异戊巴比妥N-糖基化的研究中,可能观察到单一的N-葡萄糖非对映异构体1b。

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