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. 1989;71(4):325-37.
doi: 10.1016/0009-2797(89)90108-7.

Biotransformation of terodiline. V. Stereoselectivity in hydroxylation by human liver microsomes

B Norén  1 , S Strömberg, O Ericsson, B Lindeke
Affiliations

Biotransformation of terodiline. V. Stereoselectivity in hydroxylation by human liver microsomes

B Norén et al. Chem Biol Interact. 1989.

Abstract

The stereoselective hydroxylation of N-tert-butyl-4,4-diphenyl-2-butylamine (Terodiline) was studied in human liver microsomes. Formation of the two main metabolites, N-tert-butyl-4(4-hydroxyphenyl)-4-phenyl-2-butylamine (II) and N-(2-hydroxymethyl-2-propyl)-4,4-diphenyl-2-butylamine (VI), was found to be stereoselective. R-Terodiline was preferentially transformed by phenolic hydroxylation to the 2R,4S-II and 2R,4R-II forms with a pronounced selectivity for the former. The formation rate ratio 2R,4S-II/2R,4R-II was about 6, obtained from two liver preparations. S-Terodiline was mainly hydroxylated to the alcohol 2S-VI although phenolic hydroxylation to the 2S,4S-II and 2S,4R-II also occurred, yielding about equal amounts of the two phenols.

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