Cargando…
New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites
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-1...
Autores principales: | , , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7961831/ https://www.ncbi.nlm.nih.gov/pubmed/33802606 http://dx.doi.org/10.3390/molecules26051354 |
_version_ | 1783665346399436800 |
---|---|
author | Loke, Steffen Liu, Lingyu Wenzel, Maxi Scheffler, Heike Iannone, Michele de la Torre, Xavier Schlörer, Nils Botrè, Francesco Keiler, Annekathrin Martina Bureik, Matthias Parr, Maria Kristina |
author_facet | Loke, Steffen Liu, Lingyu Wenzel, Maxi Scheffler, Heike Iannone, Michele de la Torre, Xavier Schlörer, Nils Botrè, Francesco Keiler, Annekathrin Martina Bureik, Matthias Parr, Maria Kristina |
author_sort | Loke, Steffen |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7961831 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-79618312021-03-17 New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites Loke, Steffen Liu, Lingyu Wenzel, Maxi Scheffler, Heike Iannone, Michele de la Torre, Xavier Schlörer, Nils Botrè, Francesco Keiler, Annekathrin Martina Bureik, Matthias Parr, Maria Kristina Molecules Article 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. MDPI 2021-03-03 /pmc/articles/PMC7961831/ /pubmed/33802606 http://dx.doi.org/10.3390/molecules26051354 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Loke, Steffen Liu, Lingyu Wenzel, Maxi Scheffler, Heike Iannone, Michele de la Torre, Xavier Schlörer, Nils Botrè, Francesco Keiler, Annekathrin Martina Bureik, Matthias Parr, Maria Kristina New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites |
title | New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites |
title_full | New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites |
title_fullStr | New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites |
title_full_unstemmed | New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites |
title_short | New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites |
title_sort | new insights into the metabolism of methyltestosterone and metandienone: detection of novel a-ring reduced metabolites |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7961831/ https://www.ncbi.nlm.nih.gov/pubmed/33802606 http://dx.doi.org/10.3390/molecules26051354 |
work_keys_str_mv | AT lokesteffen newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT liulingyu newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT wenzelmaxi newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT schefflerheike newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT iannonemichele newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT delatorrexavier newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT schlorernils newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT botrefrancesco newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT keilerannekathrinmartina newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT bureikmatthias newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites AT parrmariakristina newinsightsintothemetabolismofmethyltestosteroneandmetandienonedetectionofnovelaringreducedmetabolites |