Testosterone trans-4-n-butylcyclohexyl carboxylate releases continuous physiological levels of testosterone into the circulation of men or monkeys over a period of 8 to 10 weeks from an intramuscular depot and may, therefore, be an agent of choice for androgen replacement therapy. The purpose of this study was to investigate the metabolism of the ester and its side chain. The ester was hydrolysed by blood sera of guinea-pig, rabbit and rat, but not horse or man. It was slowly hydrolysed by rat and cynomolgus liver and the testosterone metabolites androstenedione and androstanediol were formed. Bucyclic acid (trans-4-n-butylcyclohexyl carboxylate) was slowly metabolized to two metabolites, M1 and M2, by cynomolgus liver homogenates. The acid metabolites were analysed by chromatography and mass spectrometry after reaction with diazomethylpyrene to form fluorescent pyrenyl esters. When compared with synthetic compounds using the criteria of chromatographic mobility and mass spectral analysis, the polar metabolite was identified as hydroxy-4-n-butylcyclohexyl carboxylate. The less polar metabolite could not be definitively identified.
Journal of Endocrinology (1994) 140, 465–473
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