Synthesis and identification of hydroxylated metabolites of the anti-estrogenic agent cyclofenil

✍ Scribed by Peter Gärtner; Karin Hofbauer; Christian Reichel; Thomas Geisendorfer; Günter Gmeiner

• Book ID: 102377152
• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 144 KB
• Volume: 43
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/jms.1462

✦ Synopsis

Abstract

The detection of metabolites of the anti‐estrogenic substance cyclofenil, listed on the World Anti‐Doping Agency (WADA) Prohibited List since 2004 is described. Target substances are hydroxylated metabolites, bearing an aliphatic hydroxyl group either in the 2‐, 3‐ or 4‐position of the aliphatic ring, in addition to the phenolic functions on the aromatic rings. Structural identification used NMR as well as high‐resolution mass spectrometry after nano‐electrospray ionisation (ESI). Unambiguous detection of all three synthesised cyclofenil metabolites M1M3 was done using gas chromatography for separation and electron ionisation mass spectrometry for detection of the per‐silylated compounds in comparison with a reference urine deriving from an excretion study within the WADA 2007 Educational Programme. Copyright © 2008 John Wiley & Sons, Ltd.