Hepatic microsomal N -demethylation of N -methylbenzamidine
Biochemical Pharmacology, ISSN: 0006-2952, Vol: 36, Issue: 19, Page: 3127-3133
1987
- 15Citations
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Metrics Details
- Citations15
- Citation Indexes15
- 15
- CrossRef14
Article Description
The microsomal oxidative N -demethylation of N -methylbenzamidine, a model compound for active substances containing the basic amidine function, was investigated. N -Methylbenzamidine was converted into benzamidine and formaldehyde by aerobic incubation with non-induced microsomal fractions of rabbit liver homogenates and NADPH. The formation of benzamidine in the incubation mixtures under widely differing conditions was assayed using a newly-developed, high-performance, ion pair, reverse-phase partition chromatographic method. Optimal reaction conditions were determined. The benzamidine formation in the incubation mixture followed Michaelis-Menten kinetics and required the presence of molecular oxygen and NADPH. The effects of the inducer phenobarbital, methylcholanthrene, ethanol and N -methylbenzamidine itself on the activity were studied. Neither Superoxide anion nor hydrogen peroxide was directly involved in the demethylation reaction. The direct involvement of cytochrome P-450 in this reaction is supported by the observation that the presence of inhibitors of cytochrome P-450, in particular of carbon monoxide, markedly decreased the rate of N -demethylation. This N -demethylation of N -methylbenzamidine proves the hypothesis that benzamidines with hydrogen atoms in the α-position to the amidine nitrogen atoms are N -dealkylated instead of N -oxygenated by the microsomal mixed function oxidase system.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/0006295287906228; http://dx.doi.org/10.1016/0006-2952(87)90622-8; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=0023199527&origin=inward; http://www.ncbi.nlm.nih.gov/pubmed/3663229; https://linkinghub.elsevier.com/retrieve/pii/0006295287906228; http://dx.doi.org/10.1016/0006-2952%2887%2990622-8; https://dx.doi.org/10.1016/0006-2952%2887%2990622-8
Elsevier BV
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