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Xenobiotica
the fate of foreign compounds in biological systems
Volume 15, 1985 - Issue 2
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Research Article

A novel metabolite of tinidazole involving nitro-group migration

, , , , &
Pages 107-113 | Received 23 Jan 1984, Published online: 22 Sep 2008
 

Abstract

1. After oral doses to dogs of 14C-tinidazole, a 5-nitroimidazolyl antiprotozoal compound, a major and previously unidentified radioactive metabolite was isolated from urine and shown by FAB mass spectrometry and n.m.r. spectroscopy to be ring-hydroxylated.

2. The exact identity of this metabolite was established by X-ray diffraction analysis as ethyl 2-(5-hydroxy-2-methyl-4-nitro-1-imidazolyl)ethyl sulphone.

3. The apparent migration of the nitro group from the 5 position in the parent drug to the 4 position in the metabolite is a novel metabolic route.

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