ISSN:
1573-904X
Keywords:
diastereomers of l-(β-D-glucopyranosyl)amobarbital
;
absolute configuration
;
X ray
;
human
;
urinary excretion
;
product enantioselectivity
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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, k f ,1b, determined from the urinary excretion of lb were lower than those previously reported for unresolved amobarbital N-glucosides. However, based on the urinary excretion of lb, 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, lb, was being observed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1015900629690
Permalink