Add time:07/18/2019         Source:sciencedirect.com

The metabolic fate of the anticonvulsant cyheptamide (AY-8682) has been investigated in animals and man. In the rat [14CONH2]cyheptamide is rapidly metabolized. Hydroxylation and conjugation are the major modes of metabolism. Cleavage of C-5 from the dibenzo-cycloheptadiene ring does not occur. 10, 11-Dihydro-10,5-(epoxymethano)-5H-dibenzo[a,d]cyclohepten-13-one (“lactone”) was isolated and fully characterized from acid-hydrolyzed urine samples of rat, rabbit, dog and man. The “lactone” is an artifact that arises from the acid-catalyzed transannular lactone formation between the C-10-hydroxyl and the C-5-carboxamide group of the true metabolite, syn-10-hydroxy-cyheptamide. Further oxidation is species dependent and in rat and man occurs at C-5 and in the dog and rabbit at C-11. syn-11-hydroxy-“lactone” and 5-hydroxy-“lactone” have been isolated and fully characterized from acid-hydrolyzed rabbit and human urine respectively. Cyheptamide also undergoes aromatic hydroxylation, and two monophenolic metabolites have been isolated. The exact position of attachment of the phenolic hydroxyl group remains to be established.

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