Metabolism of zimelidine in rat, dog and man. Identification and synthesis of the principal metabolites.
Several metabolites of (Z)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine (zimelidine) were isolated from urine of rat and dog after administration of the 14C-labelled drug. The major metabolic routes found in these species involve oxidations at both the aliphatic and aromatic nitrogen, N-demethylations and deamination of the aliphatic nitrogen. The major excretion products in urine from both rat and dog were the N-oxide of zimelidine, the deamination product 3-(4-bromophenyl)-3-(3-pyridyl)-acrylic acid and its N-oxide. Apparently, there are only minor differences between rat and dog in the metabolism of zimelidine. The N-oxide of zimelidine and the acrylic acid derivative were also identified in a human urine sample. Zimelidine was labelled with 14C in the allylic position. Most of the metabolites were synthesized in pure diastereomeric form and their configuration were shown by UV and 1H-NMR.
D000328:Adult; D000818:Animals; D000928:Antidepressive Agents / Q000378:metabolism*; D001711:Biotransformation; D001977:Brompheniramine / Q000031:analogs & derivatives / Q000378:metabolism*; D004285:Dogs; D006801:Humans; D008297:Male; D011725:Pyridines / Q000378:metabolism*; D051381:Rats; D013045:Species Specificity; D015031:Zimeldine
D000928:Antidepressive Agents; D011725:Pyridines; D015031:Zimeldine; D001977:Brompheniramine