Universität zu Köln

Guddat, S., Fusshoeller, G., Beuck, S., Thomas, A., Geyer, H., Rydevik, A., Bondesson, U., Hedeland, M., Lagojda, A., Schaenzer, W. and Thevis, M. (2013). Synthesis, characterization, and detection of new oxandrolone metabolites as long-term markers in sports drug testing. Anal. Bioanal. Chem., 405 (25). S. 8285 - 8295. HEIDELBERG: SPRINGER HEIDELBERG. ISSN 1618-2642

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Abstract

The discovery and implementation of the long-term metabolite of metandienone, namely 17 beta-hydroxymethyl-17 alpha-methyl-18-norandrost-1,4,13-trien-3-one, to doping control resulted in hundreds of positive metandienone findings worldwide and impressively demonstrated that prolonged detection periods significantly increase the effectiveness of sports drug testing. For oxandrolone and other 17-methyl steroids, analogs of this metabolite have already been described, but comprehensive characterization and pharmacokinetic data are still missing. In this report, the synthesis of the two epimeric oxandrolone metabolites-17 beta-hydroxymethyl-17 alpha-methyl-18-nor-2-oxa-5 alpha-androsta-13-en-3-one and 17 alpha-hydroxymethyl-17 beta-methyl-18-nor-2-oxa-5 alpha-androsta-13-en-3-one-using a fungus (Cunninghamella elegans) based protocol is presented. The reference material was fully characterized by liquid chromatography nuclear magnetic resonance spectroscopy and high resolution/high accuracy mass spectrometry. To ensure a specific and sensitive detection in athlete's urine, different analytical approaches were followed, such as liquid chromatography-tandem mass spectrometry (QqQ and Q-Orbitrap) and gas chromatography-tandem mass spectrometry, in order to detect and identify the new target analytes. The applied methods have demonstrated good specificity and no significant matrix interferences. Linearity (R (2) > 0.99) was tested, and precise results were obtained for the detection of the analytes (coefficient of variation < 20 %). Limits of detection (S/N) for confirmatory and screening analysis were estimated at 1 and 2 ng/mL of urine, respectively. The assay was applied to oxandrolone post-administration samples to obtain data on the excretion of the different oxandrolone metabolites. The studied specimens demonstrated significantly longer detection periods (up to 18 days) for the new oxandrolone metabolites compared to commonly targeted metabolites such as epioxandrolone or 18-nor-oxandrolone, presenting a promising approach to improve the fight against doping.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Guddat, S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Fusshoeller, G. UNSPECIFIED UNSPECIFIED UNSPECIFIED Beuck, S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Thomas, A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Geyer, H. UNSPECIFIED UNSPECIFIED UNSPECIFIED Rydevik, A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Bondesson, U. UNSPECIFIED UNSPECIFIED UNSPECIFIED Hedeland, M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Lagojda, A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Schaenzer, W. UNSPECIFIED UNSPECIFIED UNSPECIFIED Thevis, M. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-474980
DOI:	10.1007/s00216-013-7218-1
Journal or Publication Title:	Anal. Bioanal. Chem.
Volume:	405
Number:	25
Page Range:	S. 8285 - 8295
Date:	2013
Publisher:	SPRINGER HEIDELBERG
Place of Publication:	HEIDELBERG
ISSN:	1618-2642
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language HUMAN URINE; MASS-SPECTROMETRY; IONIZATION Multiple languages Biochemical Research Methods; Chemistry, Analytical Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/47498