Loke, Steffen, Liu, Lingyu, Wenzel, Maxi, Scheffler, Heike, Iannone, Michele ORCID: 0000-0003-0845-1597, de la Torre, Xavier ORCID: 0000-0001-8037-6750, Schloerer, Nils, Botre, Francesco ORCID: 0000-0001-5296-8126, Keiler, Annekathrin Martina, Bureik, Matthias ORCID: 0000-0002-9515-6248 and Parr, Maria Kristina (2021). New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites. Molecules, 26 (5). BASEL: MDPI. ISSN 1420-3049

Full text not available from this repository.

Abstract

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

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Loke, SteffenUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Liu, LingyuUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Wenzel, MaxiUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Scheffler, HeikeUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Iannone, MicheleUNSPECIFIEDorcid.org/0000-0003-0845-1597UNSPECIFIED
de la Torre, XavierUNSPECIFIEDorcid.org/0000-0001-8037-6750UNSPECIFIED
Schloerer, NilsUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Botre, FrancescoUNSPECIFIEDorcid.org/0000-0001-5296-8126UNSPECIFIED
Keiler, Annekathrin MartinaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Bureik, MatthiasUNSPECIFIEDorcid.org/0000-0002-9515-6248UNSPECIFIED
Parr, Maria KristinaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-593835
DOI: 10.3390/molecules26051354
Journal or Publication Title: Molecules
Volume: 26
Number: 5
Date: 2021
Publisher: MDPI
Place of Publication: BASEL
ISSN: 1420-3049
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
Biochemistry & Molecular Biology; Chemistry, MultidisciplinaryMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/59383

Downloads

Downloads per month over past year

Altmetric

Export

Actions (login required)

View Item View Item