Metabolism of oxybutynin:Establishment of desethyloxybutynin and oxybutynin N-oxide formation in rat liver preparations using deuterium substitution and gas chromatographic mass spectrometric analysis

Autor: Lindeke, Björn, Hallström, Gösta, Johansson, Carin, Ericsson, Örjan, Olsson, Lars-Inge, Strömberg, Signhild
Zdroj: Biomedical Mass Spectrometry; October 1981, Vol. 8 Issue: 10 p506-513, 8p
Abstrakt: Oxybutynin is rapidly metabolized in rat liver microsomes. Two major primary oxidation products were identified as N-desethyl oxybutynin and oxybutynin N-oxide. Deuterium substituted substrate was used to aid the identification. N-Desethyl oxybutynin was characterized by gas chromatography electron impact mass spectrometry as its trifluoroacetamide derivative and oxybutynin N-oxide was indicated by the presence of a decomposition product, 2-oxo-3-butenyl-2 cyclohexyl-2-phenylglycolate, as elucidated from the gas chromatographic mass spectrometric analysis. The formation of this product from synthetic oxybutynin N-oxide was verified and occurs by two consecutive rearrangements upon thermolysis of the unstable N-oxide. Attempted titanous chloride reduction of oxybutynin N-oxide resulted in the formation of the hydrolytic products 2-cyclohexyl-2-phenylglycolic acid and 4-diethylamino-2-butynol.
Databáze: Supplemental Index