Introduction

Fluoxymesterone (A1) is an anabolic steroid with less androgenic side effects than testosterone. Additionally, fluoxymesterone can stimulate the secretion of erythropoietin in humans. For both reasons, the use of fluoxymesterone is prohibited by the World Anti-Doping Agency (WADA). Most anabolic steroids are completely metabolized, and no parent compound is excreted.

Uses

Fluoxymesterone is a synthetic androgen similar in action to testosterone. It works by attaching itself to androgen receptors, which causes it to interact with the parts of the cell involved in making proteins. Fluoxymesterone is used to manage metastatic breast cancer in menopausal women who have hormone receptor-positive tumors or as a hormone replacement for men. Additionally, it is sometimes used to treat anemia.

Detection methods

Extensive literature research revealed that the analytical methods for the analysis of fluoxymesterone and its metabolites mainly focused on the use of GC–MS and LC-MS. Different studies have been performed to determine fluoxymesterone urinary metabolites by GC-MS. Kammerer et al. found that fluoxymesterone abuse can be monitored by the detection of two major metabolites: 6-hydroxyfluoxymesterone (A4) and 9-fluoro-17?-methylandrost-4-ene-3α,6β,11β,17β-tetrol (A2). Additionally, other metabolites (which included 9α-fluoro-17-methyl-5β-androstan-3,6,11,17-tetrol, 9α-fluoro-17-methyl-3,6,17-trihydroxy- androstan-11-one, and 9α-fluoro-17-methyl-5β-androstan-3,11,17-triol) were also detected in that study but at low and/or very variable concentrations. Using GC-MS, Schanzer and Donike confirmed the presence of the two major metabolites as well as 9-fluoro-18-nor-17,17-dimethyl-4,13-diene-11-ol-3-one (A3) by comparison of their EI mass spectra of the trimethylsilyl (TMS) derivatives with those obtained from synthesized reference standards.