Metabolic N-hydroxylation of substituted acetophenone imines. I. Evidence for formation of isomeric oximes

Xenobiotica; the Fate of Foreign Compounds in Biological Systems
J W Gorrod, M Christou

Abstract

A series of chemically stable substituted acetophenone imines and their potential N-hydroxylated metabolites (i.e., oximes) have been synthesized and characterized by spectroscopic methods. The enzymic N-hydroxylation of acetophenone imines in vitro has been demonstrated as a general metabolic pathway in several mammalian species including the guinea-pig. The oxime metabolites were formed as mixtures of two geometric isomers, Z (syn-phenyl) and E (anti-phenyl), wherein the phenyl and hydroxyl group are cis and trans to each other respectively. The E (anti-phenyl) isomer was the quantitatively predominant isomeric form metabolically produced by all species studied. The relative proportions of the E and Z isomers in metabolic mixtures were found to be species dependent.

References

Aug 1, 1975·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·J W GorrodA H Beckett
Nov 1, 1973·Journal of Pharmaceutical Sciences·M A SchwartzA S Leon
Aug 1, 1971·Biochemical Pharmacology·H B HuckerR E Rhodes
Jun 4, 1971·Biochemical and Biophysical Research Communications·C J ParliR E McMahon
Jun 1, 1967·Proceedings of the Society for Experimental Biology and Medicine·P D LotlikarE C Miller
Aug 1, 1983·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·B Clement

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Citations

Jan 1, 1989·Drug Metabolism and Drug Interactions·B Clement
Dec 6, 2005·Biochemical Pharmacology·Sabine HeberlingBernd Clement
Oct 1, 1990·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·J G SlatterR Burton

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