New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites.

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Loke S, Liu L, Wenzel M, Scheffler H, Iannone M, de la Torre X, Schlorer N, Botre F, Keiler AM, Bureik M, Parr MK

New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites.

Molecules. 2021 Mar 3;26(5). pii: molecules26051354. doi: 10.3390/molecules26051354.

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33802606 [ View in PubMed
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Abstract

Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17alpha-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. Following the previously reported detection of long-term metabolites with a 17xi-hydroxymethyl-17xi-methyl-18-nor-5xi-androst-13-en-3xi-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone ("oral turinabol"), in this study we investigated the formation of similar metabolites of metandienone and 17alpha-methyltestosterone with a rearranged D-ring and a fully reduced A-ring. Using a semi-targeted approach including the synthesis of reference compounds, two diastereomeric substances, viz. 17alpha-hydroxymethyl-17beta-methyl-18-nor-5beta-androst-13-en-3alpha-ol and its 5alpha-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5beta-metabolite was detected. Additionally, 3alpha,5beta-tetrahydro-epi-methyltestosterone was identified in the urines of both administrations besides the classical metabolites included in the screening procedures. Besides their applicability for anti-doping analysis, the results provide new insights into the metabolism of 17alpha-methyl steroids with respect to the order of reductions in the A-ring, the participation of different enzymes, and alterations to the D-ring.

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