Detection and characterization of a new metabolite of 17α-methyltestosterone

Titel in Übersetzung: Nachweis und Beschreibung eines neuen Metaboliten von 17α-Methyltestosteron

Oscar J. Pozo, Peter van Eenoo, Koen Deventer, Leen Lootens, Wim van Thuyne, Maria Kristina Parr, Wilhelm Schänzer, Juan V. Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels, Frans T. Delbeke

Publikation: Beitrag in FachzeitschriftZeitschriftenaufsätzeForschungBegutachtung

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. Verf.-Referat
Titel in ÜbersetzungNachweis und Beschreibung eines neuen Metaboliten von 17α-Methyltestosteron
OriginalspracheEnglisch
ZeitschriftDrug metabolism and disposition: the biological fate of chemicals
Jahrgang37
Seiten (von - bis)2153-2162
Seitenumfang10
ISSN0090-9556
PublikationsstatusVeröffentlicht - 2009

Fachgebiete und Schlagwörter

  • Doping
  • Dopinganalyse
  • Dopingkontrolle
  • Dopingnachweis
  • Flüssigkeitschromatographie
  • Gaschromatographie
  • Massenspektrometrie
  • Metabolit
  • Sportmedizin

Zitation