Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control

Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control / Maria K. Parr, Gregor Fusshöller, Nils Schlörer, Georg Opfermann, Thomas Piper, Grigory Rodchenkov, Wilhelm Schänzer. - (Rapid Communications in Mass Spectrometry 23 (2009) 2 (30 January); p. 207-218)

  • PMID: 19089863
  • DOI: 10.1002/rcm.3861


Abstract

The urinary metabolism of the irreversible aromatase inhibitor androsta-1,4,6-triene-3,17-dione was investigated. It is mainly excreted unchanged and as its 17beta-hydroxy analogue. For confirmation, 17beta-hydroxyandrosta-1,4,6-trien-3-one was synthesized and characterized by nuclear magnetic resonance (NMR) in addition to the parent compound. In addition, several reduced metabolites were detected in the post-administration urines, namely 17beta-hydroxyandrosta-1,4-dien-3-one (boldenone), 17beta-hydroxy-5beta-androst-1-en-3-one (boldenone metabolite), 17beta-hydroxyandrosta-4,6-dien-3-one, and androsta-4,6-diene-3,17-dione. The identification was performed by comparison of the metabolites with reference material utilizing gas chromatography/mass spectrometry (GC/MS) of the underivatized compounds and GC/MS and GC/tandem mass spectrometry (MS/MS) of their trimethylsilyl (TMS) derivatives. Alterations in the steroid profile were also observed, most obviously in the androsterone/testosterone ratio. Even if not explicitly listed, androsta-1,4,6-triene-3,17-dione is classified as a prohibited substance in sports by the World Anti-Doping Agency (WADA) due to its aromatase-inhibiting properties. In 2006 three samples from human routine sports doping control tested positive for metabolites of androsta-1,4,6-triene-3,17-dione. The samples were initially found suspicious for the boldenone metabolite 17beta-hydroxy-5beta-androst-1-en-3-one. Since metabolites of androst-4-ene-3,6,17-trione were also present in the urine samples, it is presumed that these findings were due to the administration of a product like 'Novedex Xtreme', which could be easily obtained from the sport supplement market.

Original document

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Science
Study
Date
16 December 2008
People
Fußhöller, Gregor
Opfermann, G.
Parr, Maria Kristina
Piper, Thomas
Rodchenkov, Grigory
Schänzer, Wilhelm
Schlörer, Nils
Country
Germany
Language
English
Other organisations
Deutsche Sporthochschule Köln (DSHS) - German Sport University Cologne
Analytical aspects
Mass spectrometry analysis
Doping classes
S1. Anabolic Agents
Substances
Androsta-1,4,6-triene-3,17-dione (androstatrienedione)
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Scientific article
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9 March 2021
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12 March 2021
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