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Molecular Pharmacology, Vol 18, 105-111, Copyright © 1980 by the American Society for Pharmacology and Experimental Therapeutics

Metabolites from the Reduction of Metronidazole by Xanthine Oxidase

EWAN J. T. CHRYSTAL 1, RONALD L. KOCH 1, and PETER GOLDMAN 1

1 Division of Clinical Pharmacology, Department of Pharmacology, Harvard Medical School, Beth Israel Hospital, Boston, Massachusetts 02215

Metronidazole is reduced by a variety of electron donors in an in vitro system containing milk xanthine oxidase. With hypoxanthine as electron donor, the products and their yields are as follows: N-(2-hydroxyethyl)-oxamic acid, 2.2%; N-glycoylethanolamine, 2.7%; N-acetylethanolamine, 2.4%; ethanolamine, 15.3%; acetate, 4.8%; acetamide, 14.1%; and glycine, 8%. Additional glycine is found when the reaction products are hydrolyzed. These products are consistent with a number of patterns of fragmentation of the imidazole ring which suggest the existence of several labile intermediates in the reduction of metronidazole.

Submitted on September 13, 1979
Accepted on March 10, 1980




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R. Kock, B. Beaulieu Jr, E. Chrystal, and P Goldman
A metronidazole metabolite in human urine and its risk
Science, January 23, 1981; 211(4480): 398 - 400.
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