Enzymic Oxidation α to the Acetylenic Group in the Metabolism of N-(5-Pyrrolidinopent-3-ynyl)- Succinimide (BL 14) in vitro

Björn Lindeke Department of Organic Pharmaceutical Chemistry, The Biomedical Center, University of Uppsala, Box 574, Uppsala, S-751 23, Sweden

Gösta Hallström Department of Organic Pharmaceutical Chemistry, The Biomedical Center, University of Uppsala, Box 574, Uppsala, S-751 23, Sweden

Elisabet Anderson Department of Organic Pharmaceutical Chemistry, The Biomedical Center, University of Uppsala, Box 574, Uppsala, S-751 23, Sweden

Bo Karlén Department of Drugs, Division of Pharmacy, National Board of Health and Welfare, Box 607, Uppsala, S-751 25, Sweden

Abstract

1. The product of α-acetylenic oxidation of N-(5-pyrrolidinopent-3-ynyl)-succinimide (BL 14) by rat liver preparations was identified as N-(5-pyrrolidino-2-hydroxypent-3-ynyl)succinimide, by mass spectral analysis of metabolites of deuterium-labelled and non-labelled substrate.

2. The synthesis and physicochemical characteristics of the metabolite are reported.

3. Substantial amounts of the metabolite were obtained in preparations from phenobarbital-treated rats, while only minute amounts were formed by non-induced preparations.

4. Evidence for the involvement of an inducible cytochrome P-450 system in effecting this α-acetylenic oxidation is presented.

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Enzymic Oxidation α to the Acetylenic Group in the Metabolism of N-(5-Pyrrolidinopent-3-ynyl)- Succinimide (BL 14) in vitro

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Enzymic Oxidation α to the Acetylenic Group in the Metabolism of N-(5-Pyrrolidinopent-3-ynyl)- Succinimide (BL 14) in vitro

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