Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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 Schloerer
ORCID logo ,
Francesco Botrè
,
Annekathrin Martina Keiler
ORCID logo ,
Matthias Bureik
ORCID logo ,
Maria Kristina Parr
* ORCID logo
Version 1 : Received: 17 February 2021 / Approved: 18 February 2021 / Online: 18 February 2021 (13:51:01 CET)
Version 2 : Received: 26 February 2021 / Approved: 1 March 2021 / Online: 1 March 2021 (13:19:54 CET)

A peer-reviewed article of this Preprint also exists.

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. 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.

Abstract

Metandienone and methyltestosterone are orally available anabolic-androgenic steroids with a 17α-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. After 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 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 identi-fied 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 hypotheses on the metabolism of 17α-methyl steroids with respect to the order of reductions in the A-ring and the participation of different enzymes.

Keywords

17α-methyl steroids; long-term metabolites; gas chromatography-mass spectrometry; 17-hydroxymethyl-17-methyl-18-nor; D-ring alteration; doping control; metabolism

Subject

Chemistry and Materials Science, Analytical Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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