5α-Androst-1-ene-3,17-dione : metabolism, influence on steroid profile and biological activity

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5α-Androst-1-ene-3,17-dione (1-AD) is listed on the World Anti-Doping Agency’s prohibited list as an “exogenous anabolic androgenic steroid”. It could be marketed in dietary supplements. An excretion study was conducted with six male volunteers, to whom were orally administered 50 mg of 1-AD in one-time application. Urine samples were collected for two weeks. The metabolites were measured as TMS-derivatives with GC/MS. The intake was detectable up to eight days based on the main metabolite 3α-hydroxy-5α-androst-1-en-17-one (1-DHA). 1-DHA was synthesized from 5α-androst-2-en-17-one via the 2,3-epoxid as an intermediate and structurally identified with GC/MS and NMR. Other identified metabolites were 17β-hydroxy-5α-androst-1-en-3-one (1-testosterone), 5α-androst-1-ene-3α,17β-diol and 5α-androst-1-ene-3β,17β-diol. Furthermore two additional metabolites, presumably 18-hydroxy-5α-androst-1-ene-3,17-dione and 19-hydroxy-5α-androst-1-ene-3,17-dione, but until now without final confirmation, as well as the parent compound, were detectable in the urine. Ratios in the endogenous urinary steroid profile typically evaluated for doping analysis were also altered. Androsterone/etiocholanolone ratio (AND/ETIO) and 5α-/5β-androstane-3α,17β-diol ratio (Adiol/Bdiol) were increased. But there were no changes in the testosterone/epitestosterone quotient. The parent substance 1-AD, the main metabolite 1-DHA, 1-testosterone and 3β-hydroxy-5α-androst-1-en-17-one (1-DHEA) were also tested in the yeast-androgen-screen, a test system for androgen receptor-mediated gene expression. An androgenic activity could be shown for all. 1-Testosterone was shown to be 10-times more potent than 1-AD and 100-times more potent than the equipotent substances 1-DHA and 1-DHEA. Verf.-Referat
Original languageEnglish
Title of host publicationRecent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante
EditorsWilhelm Schänzer, Mario Thevis, Hans Geyer, Ute Mareck
Number of pages4
PublisherSportverlag Strauß
Publication date2012
Pages197-200
Publication statusPublished - 2012
EventCologne Workshop on Dope Analysis - Köln, Germany
Duration: 26.02.201202.03.2012
Conference number: 30

ID: 185800

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