Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine

Journal of Steroid Biochemistry and Molecular Biology

Volumn 115, Issue 1-2, 2009, Pages 44-61

  Fragkaki, A G ^a,b   Angelis, Y S ^a   Tsantili Kakoulidou, A ^b   Koupparis, M ^b   Georgakopoulos, C ^a  

^a Olympic Athletic Center of Athens   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Anabolic androgenic steroids; Designer steroids; Doping control; Metabolism; Principal components analysis

Indexed keywords

5ALPHA ANDROSTAN 3 ONE; ANDROGEN; ANDROST 1 ENE 3 ONE; ANDROST 1,4 DIENE 3 ONE; ANDROST 4 ENE 3 ONE; STEROID; UNCLASSIFIED DRUG;

ANDROGEN METABOLISM; ARTICLE; COMPUTER PROGRAM; CONTROLLED STUDY; HORMONE STRUCTURE; HUMAN; PRINCIPAL COMPONENT ANALYSIS; STEROID URINE LEVEL; URINALYSIS;

ANABOLIC AGENTS; ANDROGENS; DESIGNER DRUGS; DOPING IN SPORTS; HUMANS; METABOLISM; PRINCIPAL COMPONENT ANALYSIS; STEROIDS; SUBSTANCE ABUSE DETECTION;

EID: 67349264451     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2009.02.016     Document Type: Article

References (44)

1. Fragkaki A.G., Angelis Y., Koupparis M., Tsantili-Kakoulidou A., Kokotos G., and Georgakopoulos C. Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure. Steroids 74 (2009) 172-197
2. Kicman A.T. Pharmacology of anabolic steroids. Br. J. Pharmacol. 154 (2008) 502-521
3. Kochakian C.D. Metabolites of testosterone: significance in vital economy. Steroids 55 (1990) 92-97
4. Schänzer W. Metabolism of anabolic androgenic steroids. Clin. Chem. 42 (1996) 1001-1020
5. Schänzer W., and Donike M. Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites. Anal. Chim. Acta 275 (1993) 23-48
6. Van Eenoo P., and Delbeke F. Metabolism and excretion of anabolic steroids in doping control-new steroids and new insights. J. Steroid Biochem. Mol. Biol. 101 (2006) 161-178
7. Rogozkin V.A. Metabolism of Anabolic Androgenic Steroids (1991), CRS Press Inc.
8. Jin Y., and Penning M.T. Steroid 5α-reductases and 3α-hydroxysteroid dehydrogenases: key enzymes in androgen metabolism. Best Pract. Res. Clin. Endocr. Metab. 15 (2001) 79-94
9. McTernan C.L., and Stewart P.M. Steroid metabolism in peripheral tissues. In: Mason J.I. (Ed). Genetics of Steroid Biosynthesis and Function (2002), Taylor & Francis, London and New York 339-358
10. Georgakopoulos C.G., Vonaparti A., Stamou M., Kiousi P., Lyris E., Angelis Y.S., et al. Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun. Mass Spectrom. 21 (2007) 2439-2446
11. Chen Y., Monshouwer M., and Fitch W.L. Analytical tools and approaches for metabolite identification in early drug discovery. Pharmacol. Res. 24 (2007) 248-257
12. Kulkarni S.A., Zhu J., and Blechinger S. In silico techniques for the study and prediction of xenobiotic metabolism: a review. Xenobiotica 35 (2005) 955-973
13. Anari M.R., and Baillie T.A. Bridging cheminformatic metabolite prediction and tandem mass spectrometry. Drug Discov. Today 10 (2005) 711-717
14. World Anti-Doping Agency, The World Anti-Doping Code, The 2008 Prohibited List, http://www.wada-ama.org.
15. Jackson J.E. A Users Guide to Principal Component Analysis (1991), Wiley, New York
16. Simca-P 10.5.0.0, User's Guide and Tutorial, Umetrics, Sweden, 2004.
17. Massé R., and Goudreault D. Studies on anabolic steroids - II. 18-hydroxylated metabolites of mesterolone, methenolone and stenbolone: new steroids isolated from human urine. J. Steroid Biochem. Mol. Biol. 42 (1992) 399-410
18. De Boer D., De Jong E.G., Maes R.A.A., and Van Rossum J.M. The methyl-5α-dihydrotestosterones mesterolone and drostanolone; gas chromatographic/mass spectrometric characterization of the urinary metabolites. J. Steroid Biochem. Mol. Biol. 42 (1992) 411-419
19. Parr M.K., Opfermann G., and Schänzer W. Detection of new 17-alkylated steroids on WADA 2006 list. Recent Advances in Doping Analysis (14) (2006), Sport und Buch Strauss, Cologne, Germany pp. 249-258
20. Massé R., Bi H., Ayotte C., and Dugal R. Studies on anabolic steroids II-Gas chromatographic/mass spectrometric characterization of oxandrolone urinary metabolites in man. Biomed. Environ. Mass Spectrom. 18 (1989) 429-443
21. Bi H., and Massé R. Studies on anabolic steroids-12. Epimerization and degradation of anabolic 17β-sulfate-17α-methyl steroids in human: qualitative and quantitative GC/MS analysis. J. Steroid Biochem. Mol. Biol. 42 (1992) 533-546
22. Shinohara Y., Isurugi K., and Hashimoto T. Stable isotope dilution analysis of human urinary metabolites of 17α-methyltestosterone. J. Chromatogr. B 741 (2000) 271-278
23. ®) administration to man: identification of urinary metabolites by gas chromatography-mass spectrometry. J. Steroid Biochem. 36 (1990) 659-666
24. Debruyckere G., De Sagher R., Peteghem C.V., Van Vyncht G., Maghuin-Rogister G., and De Pauw E. Gas chromatographic-mass spectrometric confirmation of a clostebol metabolite in urine. Anal. Chim. Acta 291 (1994) 155-160
25. Bowers L.D. Metabolic pattern of mibolerone. Recent Advances in Doping Analysis (3) (1995), Sport und Buch Strauss, Cologne, Germany pp. 81-82
26. Zhang Y., Wu M., Liu X., and Zhang C. Analysis of urinary metabolites of mibolerone in man by gas chromatography/tandem mass spectrometry. Recent Advances in Doping Analysis (6) (1998), Sport und Buch Strauss, Cologne, Germany pp. 65-79
27. Kohler M., Parr M.K., Opfermann G., Thevis M., Schlörer N., Marner F.-J., and Schänzer W. Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: mass spectrometric identification of urinary metabolites. Steroids 72 (2007) 278-286
28. ®) in human by gas chromatography/mass spectrometry. J. Steroid Biochem. Mol. Biol. 37 (1990) 137-144
29. Rodchenkov G., Sobolevsky T., and Sizoi V. New designer anabolic steroids from Internet. Recent Advances in Doping Analysis (14) (2006), Sport und Buch Strauss, Cologne, Germany pp. 141-150
30. Schänzer W., Geyer H., and Donike M. Metabolism of methandienone in man: identification and synthesis of conjugated excreted urinary metabolites, determination of excretion rates and gas chromatographic-mass spectrometric identification of bis-hydroxylated metabolites. J. Steroid Biochem. Mol. Biol. 38 (1991) 441-464
31. Schänzer W., and Donike M. Metabolism of boldenone in man: gas chromatographic-mass spectrometric identification of urinary metabolites and determination of excretion rates. Biol. Mass Spectrom. 21 (1992) 3-16
32. Barbarulo M.V., Buiarelli F., Ciardi M., Giarrusso A., and Rosati F. Capillary GC-MS investigation of the metabolism and excretion of oxabolone in man. J. High Res. Chromatogr. 18 (1995) 705-708
33. Dürbeck H.W., Büker I., Scheulen B., and Telin B. Gas chromatographic and capillary column gas chromatographic-mass spectrometric determination of synthetic anabolic steroids. J. Chromatogr. 167 (1978) 117-124
34. Schänzer W., Horning S., and Donike M. Metabolism of anabolic steroids in humans: synthesis of 6β-hydroxy metabolites of 4-chloro-1,2-dehydro-17α-methyltestosterone, fluoxymesterone, and methandienone. Steroids 60 (1995) 353-366
35. Massé R., Bi H., and Du P. Studies on anabolic steroids. VII. Analysis of urinary metabolites of formebolone in man by gas chromatography-mass spectrometry. Anal. Chim. Acta 247 (1991) 211-221
36. Massé R., Ayotte C., Bi H., and Dugal R. Studies on anabolic steroids. III. Detection and characterization of stanozolol urinary metabolites in humans by gas chromatography-mass spectrometry. J. Chromatogr. 497 (1989) 17-37
37. Rosi D., Newman H.C., Christiansen R.G., Schane H.P., and Potts G.O. Isolation, synthesis and biological activity of five metabolites of danazol. J. Med. Chem. 20 (1977) 349-352
38. De Oca Porto R.M., Fernandez A.R., Brito D.M., Vidal T.C., and Diaz A.L. Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human. J. Chromatogr. B 830 (2006) 178-183
39. Kim Y., Lee Y., Kim M., Yim Y.-H., and Lee W. Determination of the metabolites of gestrinone in human urine by high performance liquid chromatography, liquid chromatography/mass spectrometry and gas chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 14 (2000) 1717-1726
40. Levesque J.-F., Templeton E., Trimble L., Berthelette C., and Chauret N. Discovery, biosynthesis and structure elucidation of metabolites of a doping agent and a direct analogue, tetrahydrogestrinone and gestrinone, using human hepatocytes. Anal. Chem. 77 (2005) 3164-3172
41. De Boer D., Gainza Bernal M.E., Van Ooyen R.D., and Maes R.A.A. The analysis of trenbolone and the human urinary metabolites of trenbolone acetate by gas chromatography/mass spectrometry and gas chromatography/tandem mass spectrometry. Biol. Mass Spectrom. 20 (1991) 459-466
42. Parr M.K., Kazlauskas R., Schlörer N., Opfermann G., Piper T., Schulze G., and Schänzer W. 6α-Methylandrostenedione: gas chromatographic mass spectrometric detection in doping control. Rapid Commun. Mass Spectrom. 22 (2008) 321-329
43. ®) and its metabolites in urine by gas chromatography-mass spectrometry in relation to doping analysis. Biomed. Chromatogr. 19 (2005) 689-695
44. Parr M.K., Fuβhöller G., Schlörer N., Opfermann G., Piper T., Rodchenkov G., and Schänzer W. Metabolism of androsta-1,4,6-triene-3,17-dione and detection by gas chromatography/mass spectrometry in doping control. Rapid Commun. Mass Spectrom. 23 (2009) 207-218