Long-term metabolites of 17 methylsteroids - investigation on 18-nor-17-hydroxymethyl 17 methyl-androstane derivatives

Code: 06C04WS

Metandienone 18-nor-17β-hydroxymethyl-17α-methyl-androsta-1,4,13-trien-3-one was recently identified as a long-term metabolite in human urine. As the metabolic fate of the D-Ring of other 17-methylated steroids was found to be similar up to now, those steroids may also yield analogue metabolites. The project aims to investigate the excretion of 18-nor-17-hydroxymethyl-17-methyl-androstane derivatives in human urines after the application of different 17-methyl steroids. The structures of the respective metabolites will be confirmed by comparison with reference substances. These compounds will be synthesized and characterized by means of mass spectrometric and NMR techniques. Additionally the kinetics of the excretion will be investigated in order to determine whether these compounds are also suitable as long-term metabolites in doping control.

Main Findings

Following the administration of Bolasterone, Methandriol, 17-Methyl-19-nortestosterone, Mibolerone, Oxandrolone and Stanozolol no analogous metabolites were detected. Synthesis of 17α-hydroxymethyl-17β-methyl-18-norandrosta-1,4,13-trien-3-one from androst4-ene-3,17-dione and its NMR confirmation were successfully performed, allowing the confirmation of the stereochemistry at C-17. Chemical synthesis of 17β-hydroxymethyl-17αmethyl-18-norandrosta-1,4,13-trien-3-one as test compound failed up to now. Hence, no reference material for the new metabolites is available.