ArticleMolecules (Basel, Switzerland)2021
New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites.
Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 23 citations in OpenAlex.
- Metandienone abuse induces hepatotoxicity via dysregulated inflammation and metabolic dysfunction.The Journal of international medical research · 2026Article
- Evaluation of Different Detection and Identification Methods of Intact Tetrahydro-Methyltestosterone Sulfate Metabolites in Doping Control.Drug testing and analysis · 2026Article
- Overcoming the Challenge of Confident Identification Among Two Related Groups of 17-Methyl Steroids by GC-MS.Journal of separation science · 2025Article
- Same, but different: Variations in fragment ions among stereoisomers of a 17α-methyl steroid in gas chromatography/electron ionization mass spectrometry.Rapid communications in mass spectrometry : RCM · 2025Article
- Breaking the Bottleneck in Anticancer Drug Development: Efficient Utilization of Synthetic Biology.Molecules (Basel, Switzerland) · 2022Review
- Medaka embryos as a model for metabolism of anabolic steroids.Archives of toxicology · 2022Article
Corrections and comments
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Authors and funding
11 authors at 5 institutions in 4 countries.
Funding
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.
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