ISSN:
0899-0042
Keywords:
Chiral stereospecificity
;
esterase
;
metabolism
;
human tissue
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Famciclovir is the oral form of the potent antiherpesvirus agent, penciclovir. Hydrolysis of one of the acetyl ester groups of famciclovir creates a chiral centre leading to the possible formation of (R)- and (S)-enantiomers. During its conversion to penciclovir, famciclovir forms two chiral metabolites, namely monoacetyl-6-deoxy-penciclovir and monoacetyl-penciclovir. The absolute configuration and stereospecificity of the monoacetyl metabolites of famciclovir, produced in human intestinal wall extract, were determined using isotopically chiral famciclovir and 13C NMR spectroscopy of the isolated metabolites. 13C NMR showed that the esterase(s), in human intestinal wall extract, hydrolysed the acetyl group preferentially from the pro-(S)-acetoxymethyl group of famciclovir. The specificity of esterase action in forming monoacetyl-6-deoxy-penciclovir and monoacetyl-penciclovir was about 77 and 72%, respectively. © 1993 Wiley-Liss, Inc.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530050803
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