Gauthier, Julie; Goudreault, Danielle; Poirier, Donald et Ayotte, Christiane 
ORCID: https://orcid.org/0000-0002-6352-2071
(2009).
Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes
Steroids
, vol. 74
, nº 3.
pp. 306-314.
DOI: 10.1016/j.steroids.2008.11.002.
Résumé
Methyldrostanolone (2α,17α-dimethyl-17β-hydroxy-5α-androstan-3-one) was synthesized from drostanolone (17β-hydroxy-2α-methyl-5α-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 3α- (major) and 3β-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3α-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-d0 and TMS-d9) derivatives. Finally, on the basis of the GC-MS and 1H 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.
| Type de document: | Article |
|---|---|
| Mots-clés libres: | Methyldrostanolone; Drostanolone; Metabolites; Hepatocytes; GC–MS |
| Centre: | Centre INRS-Institut Armand Frappier |
| Date de dépôt: | 30 juin 2024 18:01 |
| Dernière modification: | 30 juin 2024 18:01 |
| URI: | https://espace.inrs.ca/id/eprint/14691 |
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