Structure proof of tibolone 3-hydroxy metabolite

Maria Kristina Parr, Jörg Daniels, Nils Schlörer, Wilhelm Schänzer

Publikation: Beitrag in Buch/Bericht/KonferenzbandKonferenzbeitrag - Aufsatz in KonferenzbandForschung

Abstract

Following the WAADS discussions on the stereochemistry of the 3-hydroxy metabolite of tibolone and confusing assignments of the stereochemistry of reference substances provided by different suppliers, we have studied the urinary excretion of tibolone with special respect to the stereochemistry of hydrogenation on C3. As already reported in previous studies, only the early eluting epimer is excreted in the glucuronide fraction. The chemical reduction of tibolone with lithium tri-t-butoxyaluminum hydride (LiR3AIH) yielded one isomer with excellent enantiomeric excess, namely the later eluting one. It was characterized by GC-MS and NMR and its structure was confirmed as 3α product by X-ray analysis. Interestingly this product elutes later than the 3β isomer, which is in contrast to the findings for 5α- and 4-ene steroids. This was confirmed by reduction of the structure analogue norethisterone within this investigation. The urinary excretion of the 3-hydroxy metabolite of tibolone in humans was reinvestigated and the metabolite detected in glucuronide fraction was proven to have 3β-OH configuration, while the urinary metabolism of 4-ene steroids follows 3α pathway. Verf.-Referat
OriginalspracheDeutsch
TitelRecent advances in doping analysis (20) : Proceedings of the Manfred-Donike-Workshop, 30th Cologne Workshop on Dope Analysis : 26th February to 2nd March 2012 2. Variante
Herausgeber*innenWilhelm Schänzer, Mario Thevis, Hans Geyer, Ute Mareck
Seitenumfang6
Herausgeber (Verlag)Sportverlag Strauß
Erscheinungsdatum2012
Seiten28-33
PublikationsstatusVeröffentlicht - 2012
VeranstaltungCologne Workshop on Dope Analysis - Köln, Deutschland
Dauer: 26.02.201202.03.2012
Konferenznummer: 30

Fachgebiete und Schlagwörter

  • Biochemie
  • Doping
  • Dopinganalyse
  • Dopingnachweis
  • Gaschromatographie
  • Massenspektrometrie
  • Screening
  • Steroid
  • Untersuchungsmethode
  • Urin
  • Urinausscheidung
  • Urinuntersuchung

Zitation