The detection of danazol and its significance in doping analysis
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This paper reports the identification of ethisterone and two stereoisomers of 2-hydroxymethylethisterone as danazol metabolites in urine using GC/MS, providing methods for doping analysis.
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Abstract
The use of anabolic steroids and related compounds in sport is forbidden by the International Olympic Committee (IOC). Because danazol (17 alpha-pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol) is structurally related to the anabolic steroid stanozolol, its use should be questioned. Therefore, the detection and the significance of danazol in doping analysis are discussed. A urine specimen suspected of containing danazol metabolites was analyzed in order to characterize the metabolites. After isolation and conversion into three different derivatives, the metabolites were subjected to gas chromatography/mass spectrometry (GC/MS) in the electron impact (EI) mode. The structure assignment was based on the molecular ions, fragmentation patterns observed for the three different derivatives, and the possible metabolite structures given in the literature. Ethisterone was identified as a nonconjugated metabolite. 2-Hydroxymethylethisterone was observed in two stereoisomeric forms. One stereoisomer was found mainly in the nonconjugated steroid fraction and the other in the conjugated fraction. The results were confirmed by analyzing urine specimens of a volunteer who was known to have taken danazol. Derivatization methods and GC/MS data are given to implement danazol detection in routine screening and confirmation procedures.
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Cited by (7)
- Danazol 2022
- Analysis of sulfate metabolites of the doping agents oxandrolone and danazol using high performance liquid chromatography coupled to tandem mass spectrometry 2016
- Square-wave adsorptive stripping voltammetric determination of danazol in capsules 2006
- Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human 2005
- Voltammetric study of danazol and its determination in capsules and spiked biological fluids 2004
- GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine 2001
- GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine 2001
Source provenance
- openalex
- last seen: 2026-05-11T06:35:44.859312+00:00
- pubmed
- last seen: 2026-10-08T21:03:30.943773+00:00
- unpaywall
- last seen: 2026-10-15T06:24:24.424788+00:00
License: CC0
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