Studies on the Metabolism of Thiourea Derivatives. II : On the Metabolites of N-Methyl-thiocarbanilide in Rabbit Urine

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Abstract
Since no report has appeared to date on the metabolism of N, N'-diaryl-N-alkylthiocarbanilide the metabolism of their typical derivative, N-methylthiocarbanilide, was studied. Examinations were made on the urinary metabolites in rabbits receiving the compound orally. Ether-soluble metabolites in the urine were examined by means of thin-layer chromatography, and unchanged N-methylthiocarbanilide, 4-hydroxy-N-methylthiocarbanilide, 4'-hydroxy-N-methylthiocarbanilide, 4, 4'-dihydroxy-N-methylthiocarbanilide, N-methylcarbanilide, 4-hydroxy-N-methylcarbanilide, 4'-hydroxy-N-methylcarbanilide, 4, 4'-dihydroxy-N-methyl-carbanilide, 4-hydroxythiocarbanilide, 4, 4'-dihydroxythiocarbanilide, and 4-hydroxyphenyliso-thiocyanate were detected, but their amount was very small. Therefore, in order to investigate the conjugates, the ether extract of the urine submitted to hydrolysis with β-glucuronidase was examined. By chromatography of the concentrated extract on silica gel column, a considerable amount of 4'-hydroxy-N-methylthiocarbanilide was isolated in crystalline form. These results suggest that the major metabolic pathway of N-methylthiocarbanilide in rabbits is hydroxylation in the 4'-position followed by conjugation with glucuronic acid, and, as a minor reaction, hydroxylation in the 4-position, N-demethylation, desulfurization, and cleavage of C-N linkage take place.

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