Structural elucidation of major selective androgen receptor modulator (SARM) metabolites for doping control

Neeraj Garg, Annelie Hansson, Heather K Knych, Scott D Stanley, Mario Thevis, Ulf Bondesson, Mikael Hedeland, Daniel Globisch

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Selective androgen receptor modulators (SARMs) are a class of androgen receptor drugs, which have a high potential to be performance enhancers in human and animal sports. Arylpropionamides are one of the major SARM classes and get rapidly metabolized significantly complicating simple detection of misconduct in blood or urine sample analysis. Specific drug-derived metabolites are required as references due to a short half-life of the parent compound but are generally lacking. The difficulty in metabolism studies is the determination of the correct regio and stereoselectivity during metabolic conversion processes. In this study, we have elucidated and verified the chemical structure of two major equine arylpropionamide-based SARM metabolites using a combination of chemical synthesis and liquid chromatography-mass spectrometry (LC-MS) analysis. These synthesized SARM-derived metabolites can readily be utilized as reference standards for routine mass spectrometry-based doping control analysis of at least three commonly used performance-enhancing drugs to unambigously identify misconduct.

Original languageEnglish (US)
Pages (from-to)698-702
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number5
DOIs
StatePublished - Jan 1 2018

Fingerprint

metabolites
Androgen Receptors
Metabolites
Modulators
modulators
Doping (additives)
drugs
Mass spectrometry
Mass Spectrometry
Performance-Enhancing Substances
mass spectroscopy
Stereoselectivity
urine
Liquid chromatography
liquid chromatography
metabolism
chromatography
Sports
Metabolism
Liquid Chromatography

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Structural elucidation of major selective androgen receptor modulator (SARM) metabolites for doping control. / Garg, Neeraj; Hansson, Annelie; Knych, Heather K; Stanley, Scott D; Thevis, Mario; Bondesson, Ulf; Hedeland, Mikael; Globisch, Daniel.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 5, 01.01.2018, p. 698-702.

Research output: Contribution to journalArticle

Garg, Neeraj ; Hansson, Annelie ; Knych, Heather K ; Stanley, Scott D ; Thevis, Mario ; Bondesson, Ulf ; Hedeland, Mikael ; Globisch, Daniel. / Structural elucidation of major selective androgen receptor modulator (SARM) metabolites for doping control. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 5. pp. 698-702.
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