title: The methyl-5 alpha-dihydrotestosterones mesterolone and drostanolone; gas chromatographic/mass spectrometric characterization of the urinary metabolites.
abstract: Before including the detection of the methyl-5 alpha-dihydrotestosterones mesterolone (1 alpha-methyl-17 beta-hydroxy-5 alpha-androstan-3-one) and drostanolone (2 alpha-methyl-17 beta-hydroxy-5 alpha-androstan-3-one) in doping control procedures, their urinary metabolites were characterized by gas chromatography/mass spectrometry. Several metabolites were found after enzymatic hydrolysis and conversion of the respective metabolites to their trimethylsilyl-enol-trimethylsilyl ether derivatives. The major metabolites of mesterolone and drostanolone were identified as 1 alpha-methyl-androsterone and 2 alpha-methyl-androsterone, respectively. The parent compounds and the intermediate 3 alpha,17 beta-dihydroxysteroid metabolites were detected as well. The reduction into the corresponding 3 beta-hydroxysteroids was a minor metabolic pathway. All metabolites were found to be conjugated to glucuronic acid.
authors.affiliation: Netherlands Institute for Drugs and Doping Research, Utrecht.
authors.forename: D
authors.initials: D
authors.lastname: de Boer
authors.forename: E G
authors.initials: EG
authors.lastname: de Jong
authors.forename: R A
authors.initials: RA
authors.lastname: Maes
authors.forename: J M
authors.initials: JM
authors.lastname: van Rossum
mesh_terms: D000732:Androstanols / Q000737:chemistry / Q000378:metabolism* / Q000652:urine; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D006900:Hydroxylation; D007664:Ketosteroids / Q000737:chemistry; D008655:Mesterolone / Q000737:chemistry / Q000378:metabolism* / Q000652:urine; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: D000732:Androstanols; D007664:Ketosteroids; D008655:Mesterolone; C100263:dromostanolone