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Xenobiotica
the fate of foreign compounds in biological systems
Volume 15, 1985 - Issue 6
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Original Article

4,5-Dimethylthiazole-N-oxide-S-oxide: A metabolite of chlormethiazole in man

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Pages 503-511 | Received 12 Jul 1984, Published online: 30 Sep 2009
 

Abstract

1. The metabolic fate of chlormethiazole in healthy male subjects has been investigated following the oral administration of a single dose of chlormethiazole edisylate.

2. Five urinary C-oxidation metabolites were identified and shown to be identical with previously reported metabolites.

3. A novel metabolite, of molecular formula C5H7NO2S, was shown by trimethylsilylation, deuterium exchange, reduction studies and by its i.r., n.m.r. and mass spectrum, to be 4,5-dimethylthiazole-N-oxide-S-oxide. This is the first reported metabolite which involves the oxidation of the two heterocyclic atoms in aromatic rings. The formation and thermal stability of the compound is ascribed to resonance stabilization.

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