The potential of urinary androstdiene markers to identify 4-androstenediol (4-ADIOL) administration in athletes

Forensic Science International

Volumn 208, Issue 1-3, 2011, Pages 129-138

  Cawley, Adam T ^a   Trout, Graham J ^a   Kazlauskas, Rymantas ^a   George, Adrian V ^b  

^a NATIONAL MEASUREMENT INSTITUTE   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Androst 2,4 diene 17 one; Androst 3,5 diene 17 one; Carbon isotope ratio ( 13C); Doping control; Gas chromatography combustion isotope ratio mass spectrometry (GC C IRMS); Gas chromatography mass spectrometry (GC MS)

Indexed keywords

4 ANDROSTENEDIOL; ANDROST 2,4 DIENE 17 ONE; ANDROST 3,5 DIENE 17 ONE; CARBON 13; OXOSTEROID; UNCLASSIFIED DRUG;

ACID CATALYZED HYDROLYSIS; ADULT; ARTICLE; ATHLETE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DOPING; GAS CHROMATOGRAPHY; GAS CHROMATOGRAPHY COMBUSTION ISOTOPE RATIO MASS SPECTROMETRY; HUMAN; HUMAN EXPERIMENT; HYDROLYSIS; MALE; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; METABOLITE; MULTIPLE DRUG DOSE; PRIORITY JOURNAL; URINALYSIS; URINARY EXCRETION;

EID: 79955465604     PISSN: 03790738     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.forsciint.2010.11.016     Document Type: Article

References (36)

1. Cawley A.T., Hine E.R., Trout G.J., George A.V., Kazlauskas R. Searching for new markers of endogenous steroid administration in athletes: "looking outside the metabolic box" Forensic Sci. Int. 2004, 143:103-114.
2. Ward R.J., Shackleton C.H.L., Lawson A.M. Gas chromatographic-mass spectrometric methods for the detection and identification of anabolic steroid drugs. Br. J. Sports Med. 1975, 9:93-97.
3. Shackleton C.H.L. Profiling steroid hormones and urinary steroids. J. Chromatogr. 1986, 379:91-156.
4. Masse R., Ayotte C., Dugal R. Studies on anabolic steroids. I. Integrated methodological approach to gas chromatographic-mass spectrometric analysis of anabolic steroids metabolites in urine. J. Chromatogr. 1989, 489:23-50.
5. Becchi M., Aguilera R., Farizon Y., Flament M.-M., Casabianca H., James P. Gas chromatography/combustion/isotope-ratio mass spectrometry analysis of urinary steroids to detect abuse of testosterone in sport. Rapid Commun. Mass Spectrom. 1994, 8:304-308.
6. Shackleton C.H.L., Roitman E., Phillips A., Chang T. Androstanediol and 5-androstenediol profiling for detecting exogenously administered dihydrotestosterone, epitestosterone, and dehydroepiandrosterone: potential use in gas chromatography isotope ratio mass spectrometry. Steroids 1997, 62:665-673.
7. Maitre A., Saudan C., Mangin P., Saugy M. Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone. J. Anal. Toxicol. 2004, 28:426-431.
8. Cawley A.T., Flenker U. The application of carbon isotope ratio mass spectrometry to doping control. J. Mass Spectrom. 2008, 43:854-864.
9. Gower D.B., Fotherby K. Biosynthesis of the androgens and oestrogens. Biochemistry of Steroid Hormones 1975, 77-90. Blackwell Scientific Publications, London. H.L.J. Makin (Ed.).
10. The World Anti-Doping Agency (WADA), 2010, Prohibited List, (accessed 15.1.10). http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/WADA_Prohibited_List_2010_EN.pdf.
11. Dietary Supplement Health and Education Act of 1994, 103rd Congress of the United States of America, Public Law 103-417.
12. Anabolic Steroid Control Act of 2004, 108th Congress of the United States of America, 2d Session, S. 2195.
13. Uralets V.P., Gillette P.A. Over-the-counter anabolic steroids 4-androsten-3,17-dione; 4-androsten-3β,17β-diol; and 19-nor-4-androsten-3,17-dione: excretion studies in men. J. Anal. Toxicol. 1999, 23:357-366.
14. Cawley A.T., Kazlauskas R., Trout G.J., Rogerson J.H., George A.V. Isotopic fractionation of endogenous anabolic steroids and its relationship to doping control in sports. J. Chromatogr. Sci. 2005, 43:32-38.
15. Makin H.L.J., Trafford D.J.H., Nolan J. Mass Spectra and GC Data of Steroids 1998, Wiley-VCH, New York, p. 55, spectrum number 0217.
16. Identification criteria for qualitative assays - incorporating mass spectrometry and chromatography. WADA Technical Document TD2003IDCR 2010, World Anti-Doping Agency, (accessed 25.6.10). http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-IS-Laboratories/WADA_TD2003IDCR_EN.pdf.
17. Eggert H., VanAntwerp C.L., Bhacca N.S., Djerassi C. Carbon-13 nuclear magnetic resonance spectra of hydroxy steroids. J. Org. Chem. 1976, 41:71-78.
18. Kirk D.N., Toms H.C., Douglas C., White K.A. A survey of the high-field 1H NMR spectra of the steroid hormones, their hydroxylated derivatives, and related compounds. J. Chem. Soc. Perkin Trans. 1990, 2:1567-1594.
19. Kirk D.N., Gaskell S.J., Marples B.A. Spectroscopic methods of steroid analysis. Steroid Analysis 1995, 56-113. Blackie Academic and Professional, London. H.L.J. Makin, D.B. Gower, D.N. Kirk (Eds.).
20. Dehennin L., Ferry M., Lafarge P., Pérès G., Lafarge J.P. Oral administration of dehydroepiandrosterone to healthy men: alteration of the urinary androgen profile and consequences for the detection of abuse in sport by GC/MS. Steroids 1998, 63:80-87.
21. Brown G.A., Vukovich M.D., King D.S. Urinary excretion of steroid metabolites after chronic androstenedione ingestion. J. Clin. Endocrinol. Metab. 2004, 89:6235-6238.
22. Donike M., Rauth S., Wolansky A. Reference ranges of urinary endogenous steroids determined by gas-chromatography/mass spectrometry. 10th Cologne Workshop on Dope Analysis (7th to 12th June 1992)-Proceedings 1993, 69-86. SPORT und BUCH Strauβ, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke, S. Rauth (Eds.).
23. Reporting and Evaluation Guidance for Testosterone, Epitestosterone, T/E Ratio and Other Endogenous Steroids. WADA Technical Document TD2004EAAS 2010, World Anti-Doping Agency, (accessed 25.6.10). http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-IS-Laboratories/WADA_TD2004EAAS_EN.pdf.
24. Cawley A.T., Kazlauskas R., Trout G.J., George A.V., Silk A.J., Marshall-Gradisnik S., Weatherby R. Catching the cheats: advances in the detection of endogenous steroid abuse in sport. Chem. Aust. 2006, 73:3-7.
25. Gower D.B. Catabolism and excretion of steroids. Biochemistry of Steroid Hormones 1975, 149-164. Blackwell Scientific Publications, London. H.L.J. Makin (Ed.).
26. Makin H.L.J., Trafford D.J.H., Nolan J. Mass Spectra and GC Data of Steroids 1998, Wiley-VCH, New York, p. 5, spectrum number 0017.
27. Gower D.B., Houghton E., Kicman A.T. Anabolic steroids: metabolism, doping and detection in equestrian and human sports. Steroid Analysis 1995, 505-508. Blackie Academic and Professional, London. H.L.J. Makin, D.B. Gower, D.N. Kirk (Eds.).
28. Thevis M., Schänzer W. Mass spectrometry in sports drug testing: structure characterization and analytical assays. Mass Spectrom. Rev. 2007, 26:79-107.
29. de Boer D. Profiling Anabolic Androgens and Corticosteroids in Doping Analysis 1992, Proefschrift, Groningen, pp. 38-39.
30. Tökés L., LaLonde R.T., Djerassi C. Mass spectrometry in structural and stereochemical problems. CXXVI. Synthesis and fragmentation behaviour of deuterium-labelled 17-keto steroids. J. Org. Chem. 1967, 32:1012-1019.
31. M. Thevis, Personal communication, 8.3.2007.
32. Ishihara T., Sugimoto I. Gas chromatographic determination of degradation products and stability of dehydroepiandrosterone sulfate in aqueous solution. Drug Dev. Ind. Pharm. 1979, 5:263-275.
33. Burrows H., Cook J.W., Margaret E., Roe F., Warren F.L. Isolation of Δ3:5-androstadiene-17-one from the urine of a man with a malignant tumour of the adrenal cortex. Biochem. J. 1937, 31:950-961.
34. Wolfe J.K., Fieser L.F., Friedgood H.B. Nature of the androgens in female adrenal tumor urine. J. Am. Chem. Soc. 1941, 63:582-593.
35. Dobriner K., Lieberman S., Rhoads C.P. Studies in steroids metabolism. I. Methods for the isolation and quantitative estimation of neutral steroids present in human urine. J. Biol. Chem. 1948, 172:241-261.
36. Bradlow H.L. The hydrolysis of steroid conjugates. Chemical and Biological Aspects of Steroid Conjugation 1970, 132-181. Springer-Verlag, New York. S. Bernstein, S. Solomon (Eds.).