title: [Isolation and identification of some metabolites of mephenoxalone (Control-OM) from human urine (author's transl)].
abstract: Mephenoxalone (5-(o-methoxyphenoxymethyl)-2-oxazolidone) is degraded by various routes in the human, and some is excreted unchanged. In the metabolism of mephenoxalone, the phenoxymethyl ether bond is cleaved; thus o-methoxyphenol (metabolite I) was identified in urine, and 3-amino-1,2-propanediol (IIa) was found after alkaline hydrolysis. Hydroxylation of the benzene ring produces a phenolic hydroxymephenoxalone (metabolite III), and demethylation converts mephenoxalone into demethylmepheonxalone (metabolite IV). Opening of the oxazolidone ring leads to the production of 1-(o-methoxyphenoxy)-3-aminopropane-2-ol(metabolite V). Urine contains two further substances: 1-(o-hydroxyphenoxy)-3-aminopropene (metabolite VI) and dehydromephenoxalone (metabolite VII). Metabolite VI may be an artefact. Compounds III, IV and VII could only be detected after acid hydrolysis and enzymic cleavage with beta-glucuronidase/aryl sulphatase, whereas V and VI were detected only after acid hydrolysis. Thin layer chromatography revealed three further metabolites, which were not identified.
mesh_terms: D000328:Adult; D001711:Biotransformation; D002855:Chromatography, Thin Layer; D006801:Humans; D008297:Male; D013058:Mass Spectrometry; D010080:Oxazoles / Q000652:urine*
chemical_list: D010080:Oxazoles
vernacular_title: Isolierung einiger Metaboliten des Mephenoxalone (Control-OM) aus menschlichem Harn und ihre Identifizierung