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Detection and Characterization of a New Metabolite of 17α-Methyltestosterone

Óscar J. Pozo, Peter Van Eenoo, Koen Deventer, Leen Lootens, Wim Van Thuyne, Maria K. Parr, Wilhelm Schänzer, Juan V. Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels and Frans T. Delbeke
Drug Metabolism and Disposition November 2009, 37 (11) 2153-2162; DOI: https://doi.org/10.1124/dmd.109.028373
Óscar J. Pozo
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Peter Van Eenoo
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Koen Deventer
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Leen Lootens
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Wim Van Thuyne
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Maria K. Parr
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Wilhelm Schänzer
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Juan V. Sancho
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Felix Hernández
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Philip Meuleman
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Geert Leroux-Roels
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Frans T. Delbeke
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Abstract

The misuse of the anabolic steroid methyltestosterone is currently routinely monitored in doping control laboratories by gas chromatography-mass spectrometry (GC-MS) of two of its metabolites: 17α-methyl-5β-androstane-3α,17β-diol and 17α-methyl-5α-androstane-3α,17β-diol. Because of the absence of any easy ionizable moiety, these metabolites are poorly detectable using liquid chromatography-tandem mass spectrometry (LC-MS/MS) with electrospray ionization (ESI). In this study, the metabolism of methyltestosterone has been reinvestigated by the use of a precursor ion scan method in LC-ESI-MS/MS. Two metabolites have been detected using this method. Both compounds have been confirmed in postadministration urine samples of an urokinase plasminogen activator-severe combined immunodeficiency (uPA-SCID) mouse with humanized liver and were characterized by LC-MS/MS and GC-MS using both quadrupole and time of flight analyzers. From the detailed study of the fragmentation, these metabolites were proposed to be epimethyltestosterone and a dehydrogenated compound. Epimethyltestosterone has previously been described as a minor metabolite, whereas the occurrence of the oxidized metabolite has not been reported. Comparison with the synthesized reference revealed that the structure of the dehydrogenated metabolite is 6-ene-epimethyltestosterone. A selected reaction monitoring method including three transitions for each metabolite has been developed and applied to samples from an excretion study and to samples declared positive after GC-MS analysis. 6-Ene-epimethyltestosterone was found in all samples, showing its applicability in the detection of methyltestosterone misuse.

  • WADA, World Anti-Doping Agency
  • GC, gas chromatography
  • MS, mass spectrometry
  • LC, liquid chromatography
  • MS/MS, tandem mass spectrometry
  • TOF, time of flight
  • uPA-SCID, urokinase plasminogen activator-severe combined immunodeficiency
  • QTOF, quadripole time of flight
  • HPLC, high-performance liquid chromatography
  • CID, collision-induced dissociation
  • ESI, electrospray ionization
  • EI, electron ionization
  • SIM, selected ion monitoring
  • SRM, selected reaction monitoring
  • TMS, trimethylsilyl
  • OE+, odd electron ion(s).

Footnotes

  • This study was supported by the World Anti-Doping Agency; the Belgian State [IUAP P6/36-HEPRO]; and Ghent University via the Special Research Fund and a Concerted Action Grant [01G00507].

  • Article, publication date, and citation information can be found at http://dmd.aspetjournals.org.

    doi:10.1124/dmd.109.028373

    • Received May 4, 2009.
    • Accepted August 17, 2009.
  • Copyright © 2009 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 37 (11)
Drug Metabolism and Disposition
Vol. 37, Issue 11
November 2009
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OtherArticle

Detection and Characterization of a New Metabolite of 17α-Methyltestosterone

Óscar J. Pozo, Peter Van Eenoo, Koen Deventer, Leen Lootens, Wim Van Thuyne, Maria K. Parr, Wilhelm Schänzer, Juan V. Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels and Frans T. Delbeke
Drug Metabolism and Disposition November 1, 2009, 37 (11) 2153-2162; DOI: https://doi.org/10.1124/dmd.109.028373

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OtherArticle

Detection and Characterization of a New Metabolite of 17α-Methyltestosterone

Óscar J. Pozo, Peter Van Eenoo, Koen Deventer, Leen Lootens, Wim Van Thuyne, Maria K. Parr, Wilhelm Schänzer, Juan V. Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels and Frans T. Delbeke
Drug Metabolism and Disposition November 1, 2009, 37 (11) 2153-2162; DOI: https://doi.org/10.1124/dmd.109.028373
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