Mass spectrometric description of novel oxymetholone and desoxymethyltestosterone metabolites identified in human urine and their importance for doping control

Drug Testing and Analysis

Volumn 4, Issue 9, 2012, Pages 682-691

  Sobolevsky, Tim ^a   Rodchenkov, Grigory ^a  

^a Moscow Antidoping Centre   (Russian Federation)

Author keywords

Antidoping analysis; Desoxymethyltestosterone; GC MS MS; Long term metabolite; Oxymetholone

Indexed keywords

BIOMOLECULES; BODY FLUIDS; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPIDS; MASS SPECTROMETRY;

ANABOLIC STEROID; ANTIDOPING ANALYSE; DESOXYMETHYLTESTOSTERONE; DOPING CONTROL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY/MS; GASCHROMATOGRAPHY-MASS SPECTROMETRY; HUMAN URINE; LONG-TERM METABOLITE; OXYMETHOLONE; URINE SAMPLE;

METABOLITES;

DESOXYMETHYLTESTOSTERONE; OXYMETHOLONE; STEROID; UNCLASSIFIED DRUG;

ADULT; ARTICLE; DOPING; DRUG DETERMINATION; DRUG EXTRAVASATION; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; LABORATORY TEST; MALE; MASS FRAGMENTOGRAPHY; NORMAL HUMAN; PRIORITY JOURNAL; URINALYSIS;

EID: 84866774868     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1407     Document Type: Article

References (28)

1. World Anti-Doping Agency. The 2012 Prohibited List. International Standard. Available at: http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf [15 March 2012].
2. World Anti-Doping Agency. 2010 Laboratory Statistics. Available at: http://www.wada-ama.org/Documents/Resources/Statistics/Laboratory_Statistics/WADA_2010_Laboratory_Statistics_Report.pdf [15 March 2012].
3. N.T. Shahidi A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids. Clin. Ther. 2001, 23, 1355.
4. H.J. Ringold, E. Batres, O. Halpern, E. Necoechea Steroids. CV. 2-Methyl and 2-hydroxymethylene-androstane derivatives. J. Am. Chem. Soc. 1959, 81, 427.
5. A.M. Pavlatos, O. Fultz, M.J. Monberg, A. Vootkur Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid. Clin. Ther. 2001, 23, 789.
6. M.H. Sekera, B.D. Ahrens, Y.C. Chang, B. Starcevic, C. Georgakopoulos, D.H. Catlin Another designer steroid: discovery, synthesis, and detection of 'madol' in urine. Rapid Commun. Mass Spectrom. 2005, 19, 781.
7. C. Ayotte, D. Goudreault, D. Cyr, J. Gauthier, P. Ayotte, C. Larochelle, et al. Characterisation of chemical and pharmacological properties of new steroids related to doping of athletes, in Recent Advances in Doping Analysis, (Eds: W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck ). SPORTVERLAG Strauss, Köln, 2006, pp. 151-160.
8. World Anti-Doping Agency. Funded Project: 'Characterization of Chemical and Pharmacological Properties of New Steroids Related to Doping of Athletes'. Available at: http://www.wada-ama.org/Documents/Science_Medicine/Funded_Research_Projects/ 2004/04D35CA%20Ayotte.pdf [20 March 2012].
9. P. Diel, A. Friedel, H. Geyer, M. Kamber, U. Laudenbach-Leschowsky, W. Schänzer, et al. Characterisation of the pharmacological profile of desoxymethyltestosterone (Madol), a steroid misused for doping. Toxicol. Lett. 2007, 169, 64.
10. US Food and Drug Administration. Warning on Body Building Products Marketed as Containing Steroids or Steroid-Like Substances. Available at: http://www.fda.gov/forconsumers/consumerupdates/ucm173739.htm [20 March 2012].
11. Drug Enforcement Administration, Department of Justice. Classification of three steroids as schedule III anabolic steroids under the Controlled Substances Act. Final rule. Fed. Regist. 2009, 74, 63603.
12. P.M. Adhikary, R.A. Harkness The use of carbon skeleton chromatography for the detection of steroid drug metabolites: the metabolism of anabolic steroids in man. Acta Endocrinol. (Copenh). 1971, 67, 721.
13. B.S. MacDonald, P.J. Sykes, B.H. Kilshaw, R.A. Harkness Metabolism of the hydroxymethylene group in the anabolic steroid, oxymetholone: isolation and identification of two major metabolites (abstract). J. Endocrinol. 1973, 59, 18.
14. R. Massé, C. Ayotte, R. Dugal Studies on anabolic steroids. I. Integrated methodological approach to the gas chromatographic-mass spectrometric analysis of anabolic steroid metabolites in urine. J. Chromatogr. 1989, 489(1), 23.
15. R. Massé, H. Bi, C. Ayotte, P. Du, H. Gélinas, R. Dugal Studies on anabolic steroids. V. Sequential reduction of methandienone and structurally related steroid A-ring substituents in humans: gas chromatographic-mass spectrometric study of the corresponding urinary metabolites. J. Chromatogr. 1991, 562, 323.
16. H. Bi, P. Du, R. Massé Studies on anabolic steroids--8. GC/MS characterization of unusual seco acidic metabolites of oxymetholone in human urine. J. Steroid Biochem. Mol. Biol. 1992, 42(2), 229.
17. H. Bi, R. Massé, G. Just Studies on anabolic steroids. 10. Synthesis and identification of acidic urinary metabolites of oxymetholone in a human. Steroids 1992, 57, 453.
18. M.K. Parr, W. Schänzer Detection of the misuse of steroids in doping control. J. Steroid Biochem. Mol. Biol. 2010, 121, 528.
19. V. Vladimirova, A. Tsoutsoulova-Draganova, M. Angelova Detection, identification and excretion profile of oxymetholone metabolites in urine, in 10th Cologne Workshop On Dope Analysis, (Eds: M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke, S. Rauth ). Sport und Buch Strauss, Köln, 1993, pp. 101-120.
20. M. Lekić, M. Sober, B. Nikolin Identification of oxymetholone metabolites in the urine using gas chromatography-mass spectrometry. Med. Arh. 1992, 46, 5.
21. G. Rodchenkov, T. Sobolevsky, V. Sizoi New Designer Anabolic Steroids from Internet, in Recent Advances in Doping Analysis, (Eds: W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck ). SPORTVERLAG Strauss, Köln, 2006, pp. 151-160.
22. J. Gauthier, D. Poirier, C. Ayotte Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes. Steroids 2012, 77, 635.
23. W. Schänzer, H. Geyer, G. Fusshöller, N. Halatcheva, M. Kohler, M.K. Parr, et al. Mass spectrometric identification and characterization of a new long-term metabolite of methandienone in human urine. Rapid Commun. Mass Spectrom. 2006, 20, 2252.
24. T. Sobolevsky, G. Rodchenkov Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine. J. Steroid Biochem. Mol. Biol. 2012, 128, 121.
25. W. Schänzer, G. Opfermann, M. Donike 17-Epimerization of 17alpha-methyl anabolic steroids in humans: metabolism and synthesis of 17alpha-hydroxy-17beta-methyl steroids. Steroids 1992, 57, 537.
26. W. Schänzer Metabolism of anabolic androgenic steroids. Clin. Chem. 1996, 42, 1001.
27. M.K. Parr, G. Fusshöller, M. Gütschow, C. Hess, W. Schänzer GC-MS(/MS) investigations on long-term metabolites of 17-methyl steroids, in Recent Advances in Doping Analysis, (Eds: W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck ). SPORTVERLAG Strauss, Köln, 2010, pp. 64-73.
28. B. Disse, L. Siekmann, H. Breuer Biosynthesis of 16alpha, 17alpha-epoxy-4-androsten-3-one in rat liver microsomes. Acta Endocrinol (Copenh). 1980, 95, 58.