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Article

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

1
Institute of Pharmacy, Pharmaceutical and Medicinal Chemistry, Freie Universität Berlin, Königin-Luise-Straße 2+4, 14195 Berlin, Germany
2
Laboratorio Antidoping FMSI, Largo Giulio Onesti 1, 00197 Rome, Italy
3
Institute for Organic Chemistry, Universität zu Köln, Grenstraße 4, 50939 Cologne, Germany
4
REDs–Research and Expertise in Antidoping Sciences, ISSUL–Institute del Sciences du Sport de l’Université de Lausanne, 1015 Lausanne, Switzerland
5
Institute of Doping Analysis & Sports Biochemistry Dresden, Dresdner Str. 12, 01731 Kreischa, Germany
6
Environmental Monitoring & Endocrinology, Faculty of Biology, Technische Universität Dresden, Zellescher Weg 20b, 01217 Dresden, Germany
7
School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, China
*
Author to whom correspondence should be addressed.
Academic Editors: Christoph Müller and Franz Bracher
Received: 17 February 2021 / Revised: 26 February 2021 / Accepted: 27 February 2021 / Published: 3 March 2021
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. View Full-Text
Keywords: 17α-methyl steroids; long-term metabolites; gas chromatography-mass spectrometry; 17-hydroxymethyl-17-methyl-18-nor; D-ring alteration; doping control; metabolism 17α-methyl steroids; long-term metabolites; gas chromatography-mass spectrometry; 17-hydroxymethyl-17-methyl-18-nor; D-ring alteration; doping control; metabolism
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MDPI and ACS Style

Loke, S.; Liu, L.; Wenzel, M.; Scheffler, H.; Iannone, M.; de la Torre, X.; Schlörer, N.; Botrè, F.; Keiler, A.M.; Bureik, M.; Parr, M.K. New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites. Molecules 2021, 26, 1354. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26051354

AMA Style

Loke S, Liu L, Wenzel M, Scheffler H, Iannone M, de la Torre X, Schlörer N, Botrè 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; 26(5):1354. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26051354

Chicago/Turabian Style

Loke, Steffen; Liu, Lingyu; Wenzel, Maxi; Scheffler, Heike; Iannone, Michele; de la Torre, Xavier; Schlörer, Nils; Botrè, Francesco; Keiler, Annekathrin M.; Bureik, Matthias; Parr, Maria K. 2021. "New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites" Molecules 26, no. 5: 1354. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26051354

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