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

New Insights into the Metabolism of Methyltestosterone and Metandienone : Detection of Novel A-Ring Reduced Metabolites / Steffen Loke, Lingyu Liu, Maxi Wenzel, Heike Scheffler, Michele Iannone, Xavier de la Torre, Nils Schlörer, Francesco Botrè, Annekathrin Martina Keiler, Matthias Bureik, Maria Kristina Parr. - (Molecules 26 (2021) 5 (March 3); 1354)

  • PMID: 33802606
  • PMCID: PMC7961831
  • DOI: 10.3390/molecules26051354


Abstract

Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17α-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 17ξ-hydroxymethyl-17ξ-methyl-18-nor-5ξ-androst-13-en-3ξ-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone ("oral turinabol"), in this study we investigated the formation of similar metabolites of metandienone and 17α-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. 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol and its 5α-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5β-metabolite was detected. Additionally, 3α,5β-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 17α-methyl steroids with respect to the order of reductions in the A-ring, the participation of different enzymes, and alterations to the D-ring.

Original document

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Science
Study
Date
3 March 2021
People
Botrè, Francesco
Bureik, Matthias
de la Torre, Xavier
Iannone, Michele
Keiler, Annekathrin Martina
Liu, Lingyu
Loke, Steffen
Parr, Maria Kristina
Scheffler, Heike
Schlörer, Nils
Wenzel, Maxi
Country
China
Germany
Italy
Switzerland
Language
English
Other organisations
Freie Universität Berlin (FU Berlin) - Free University of Berlin
Technische Universität Dresden (TU Dresden) - Technical University of Dresden
Tianjin University (TJU)
Universität zu Köln - University of Cologne
Université de Lausanne (UNIL) - University of Lausanne
Laboratories
Kreischa, Germany: Institute of Doping Analysis and Sports Biochemistry (IDAS)-Dresden
Roma, Italia: Laboratorio Antidoping FMSI
Analytical aspects
Mass spectrometry analysis
Metabolization
Testing method development
Doping classes
S1. Anabolic Agents
Substances
Metandienone (17β-hydroxy-17α-methylandrosta-1,4-dien-3-one)
Methyltestosterone
Document category
Scientific article
Document type
Pdf file
Date generated
14 April 2021
Date of last modification
23 April 2021
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  • Science
  • Statistics
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  • Doping classes
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