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Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes.

Abstract : Methyldrostanolone (2alpha,17alpha-dimethyl-17beta-hydroxy-5alpha-androstan-3-one) was synthesized from drostanolone (17beta-hydroxy-2alpha-methyl-5alpha-androstan-3-one) and identified in commercial products. Cultures of cryopreserved human hepatocytes were used to study the biotransformation of drostanolone and its 17-methylated derivative. For both steroids, the common 3alpha- (major) and 3beta-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3alpha-hydroxysteroid dehydrogenase. Structures corresponding to hydroxylated metabolites in C-12 (minor) and C-16 were proposed for other metabolites based upon the evaluation of the mass spectra of the pertrimethylsilyl (TMS-d(0) and TMS-d(9)) derivatives. Finally, on the basis of the GC-MS and (1)H NMR data and through chemical synthesis of the 17-methylated model compounds, structures could be proposed for metabolites hydroxylated in C-2. All the metabolites extracted from hepatocyte culture medium were present although in different relative amounts in urines collected following the administration to a human volunteer, therefore confirming the suitability of the cryopreserved hepatocytes to generate characteristic metabolites and study biotransformation of new steroids.
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https://hal-riip.archives-ouvertes.fr/pasteur-00819932
Contributor : Charles M. Dozois <>
Submitted on : Thursday, May 2, 2013 - 8:02:22 PM
Last modification on : Monday, July 20, 2020 - 1:06:04 PM

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Julie Gauthier, Danielle Goudreault, Donald Poirier, Christiane Ayotte. Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes.. Steroids, Elsevier, 2009, 74 (3), pp.306-14. ⟨10.1016/j.steroids.2008.11.002⟩. ⟨pasteur-00819932⟩

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