Detection of the misuse of steroids in doping control

Journal of Steroid Biochemistry and Molecular Biology

Volumn 121, Issue 3-5, 2010, Pages 528-537

  Parr, Maria Kristina ^a   Schänzer, Wilhelm ^a  

^a GERMAN SPORT UNIVERSITY COLOGNE   (Germany)

Author keywords

Anabolic androgenic steroids; Aromatase inhibitors; Designer steroids; Doping control; Glucocorticosteroids; Steroidal diuretics

Indexed keywords

ANABOLIC AGENT; AROMATASE INHIBITOR; BETA GLUCURONIDASE; BETAMETHASONE; BOLDENONE; BUDESONIDE; CANRENONE; DEXAMETHASONE; DROSTANOLONE; GLUCOCORTICOID; GLUCURONIDE; METANDIENONE; METENOLONE; METHYLTESTOSTERONE; NANDROLONE; SPIRONOLACTONE; STANOZOLOL; STEROID HORMONE; TIBOLONE;

DIET SUPPLEMENTATION; DOPING; DRUG APPROVAL; DRUG LABELING; EXTRACTION; FOLLOW UP; GAS CHROMATOGRAPHY; HORMONE DETERMINATION; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; REVIEW; SCREENING TEST; STEROID METABOLISM; URINALYSIS; URINARY EXCRETION;

ANABOLIC AGENTS; CHROMATOGRAPHY, LIQUID; DOPING IN SPORTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; STEROIDS; SUBSTANCE ABUSE DETECTION; TANDEM MASS SPECTROMETRY;

EID: 77955417836     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2009.12.008     Document Type: Review

References (132)

1. World Anti-Doping Agency, World anti-doping code, 2008, online at , 27 July 2009. http://www.wada-ama.org/rtecontent/document/codev2009_En.pdf.
2. World Anti-Doping Agency, The 2009 prohibited list, 2008, online at , 05 February 2009. http://www.wada-ama.org/rtecontent/document/2009_Prohibited_List_ENG_Final_20_Sept_08.pdf.
3. World Anti-Doping Agency, Adverse analytical findings reported by accredited laboratories, online at , 11 November 2008. http://www.dopinginfo.de/.
4. Schänzer W. Sample preparation and determination of anabolic-steroids. Fresen. Z. Anal. Chem. 1988, 330(4-5):339-1339.
5. Donike M. N-methyl-n-trimethylsilyl-trifluoroacetamide a new silylating agent from series of silylated amides. J. Chromatogr. 1969, 42(1):103-104.
6. W. Schänzer, Analytik von Dopingsubstanzen-Derivatisierung, 2001, online at , 15 February 2009. http://www.dopinginfo.de/.
7. Donike M., Zimmermann J. Preparation of trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl enol ethers from ketosteroids for investigations by gas-chromatography and mass-spectrometry. J. Chromatogr. 1980, 202(3):483-486.
8. Geyer H., Schänzer W., Mareck-Engelke U., Nolteernsting E., Opfermann G. Screening procedure for anabolic steroids-control of hydrolysis with deuterated androsterone glucuronide and studies with direct hydrolysis. Recent Advances in Doping Analysis (5) 1998, 99-102. Sport und Buch Strauss, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
9. Mareck U., Thevis M., Guddat S., Gotzmann A., Bredehöft M., Geyer H., Schänzer W. Comprehensive sample preparation for anabolic steroids, glucocorticosteroids, beta-receptor blocking agents, selected anabolic androgenic steroids and buprenorphine in human urine. Recent Advances in Doping Analysis (12) 2004, 65-69. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
10. World Anti-Doping Agency, Wada technical document td2003idcr, 2004, online at , 15 February 2009. http://www.wada-ama.org/rtecontent/document/criteria_1_2.pdf.
11. Schänzer W., Geyer H., Gotzmann A., Horning S., Mareck-Engelke U., Nitschke R., Nolteernsting E., Donike M. Endogenous production and excretion of boldenone (17β-hydroxyandrosta-1,4-dien-3-one), an androgenic anabolic steroid. Recent Advances in Doping Analysis (2) 1995, 211-1211. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
12. Reznik Y., Dehennin L., Coffin C., Mahoudeau J., Leymarie P. Urinary nandrolone metabolites of endogenous origin in man: a confirmation by output regulation under human chorionic gonadotropin stimulation. J. Clin. Endocrinol. Metab. 2001, 86(1):146-150.
13. Dehennin L., Bonnaire Y., Plou P. Urinary excretion of 19-norandrosterone of endogenous origin in man: quantitative analysis by gas chromatography-mass spectrometry. J. Chromatogr. B: Biomed. Sci. Appl. 1999, 721(2):301-307.
14. Le Bizec B., Bryand F., Gaudin I., Monteau F., Poulain F., Andre F. Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin. Steroids 2002, 67(2):105-110.
15. Mareck-Engelke U., Schulze G., Geyer H., Schänzer W. The appearance of urinary 19-norandrosterone during pregnancy. Eur. J. Sport Sci. 2002, 2:2.
16. Bricout V., Wright F. Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances?. Eur. J. Appl. Physiol. 2004, 92(1-2):1-12.
17. de Geus B., Delbeke F., Meeusen R., Van Eenoo P., De Meirleir K., Busschaert B. Norandrosterone and noretiocholanolone concentration before and after submaximal standardized exercise. Int. J. Sport Med. 2004, 25(7):528-532.
18. Hebestreit M., Flenker U., Fussholler G., Geyer H., Guntner U., Mareck U., Piper T., Thevis M., Ayotte C., Schanzer W. Determination of the origin of urinary norandrosterone traces by gas chromatography combustion isotope ratio mass spectrometry. Analyst 2006, 131(9):1021-1026.
19. Verheyden K., Noppe H., Vanhaecke L., Wille K., Bussche J.V., Bekaert K., Thas O., Janssen C.R., De Brabander H.F. Excretion of endogenous boldione in human urine: influence of phytosterol consumption. J. Steroid Biochem. Mol. Biol. 2009, 117(1-3):8-14.
20. Schänzer W. Metabolism of anabolic androgenic steroids. Clin. Chem. 1996, 42(7):1001-1020.
21. Rendic S., Nolteernsting E., Schänzer W. Metabolism of anabolic steroids by recombinant human cytochrome p450 enzymes: gas chromatographic-mass spectrometric determination of metabolites. J. Chromatogr. B 1999, 735(1):73-83.
22. Baume N., Mahler N., Kamber M., Mangin P., Saugy M. Research of stimulants and anabolic steroids in dietary supplements. Scand. J. Med. Sci. Sports 2006, 16(1):41-48.
23. Delbeke F.T., Van Eenoo P., Van Thuyne W., Desmet N. Prohormones and sport. J. Steroid Biochem. Mol. Biol. 2002, 83(1-5):245-251.
24. Kamber M., Baume N., Saugy M., Rivier L. Nutritional supplements as a source for positive doping cases?. Int. J. Sport Nutr. Exerc. 2001, 11(2):258-263.
25. Van Thuyne W., Delbeke F.T. Validation of a GC-MS screening method for anabolizing agents in solid nutritional supplements. Biomed. Chromatogr. 2004, 18(3):155-159.
26. Geyer H., Mareck-Engelke U., Reinhart U., Thevis M., Schänzer W. Positive dopingfälle mit norandrosteron durch verunreinigte nahrungsergänzungsmittel. Dt. Z. Sportmed. 2000, 51(11):378-382.
27. Geyer H., Parr M.K., Mareck U., Reinhart U., Schrader Y., Schänzer W. Analysis of non-hormonal nutritional supplements for anabolic-androgenic steroids-results of an international study. Int. J. Sport Med. 2004, 25(2):124-129.
28. Geyer H., Parr M.K., Koehler K., Mareck U., Schanzer W., Thevis M. Nutritional supplements cross-contaminated and faked with doping substances. J. Mass Spectrom. 2008, 43(7):892-902.
29. Parr M.K., Geyer H., Reinhart U., Schänzer W. Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit. Contam. 2004, 21(7):632-640.
30. World Anti-Doping Agency, Wada technical document td2004eaas, 2004, online at , 12 April 2007. http://www.wada-ama.org/rtecontent/document/end_steroids_aug_04.pdf.
31. Donike M., Barwald K.R., Klostermann K., Schanzer W., Zimmermann J. The detection of exogenous testosterone. Int. J. Sport Med. 1983, 4(1):68-168.
32. Dehennin L., Matsumoto A.M. Long-term administration of testosterone enanthate to normal men: alterations of the urinary profile of androgen metabolites potentially useful for detection of testosterone misuse in sport. J. Steroid Biochem. Mol. Biol. 1993, 44(2):179-189.
33. Donike M., Ueki M., Kuroda Y., Geyer H., Nolteernsting E., Rauth S., Schänzer W., Schindler U., Volker E., Fujisaki M. Detection of dihydrotestosterone (dht) doping: alterations in the steroid profile and reference ranges for dht and its 5alpha-metabolites. J. Sport Med. Phys. Fit. 1995, 35(4):235-250.
34. Geyer H., Schänzer W., Mareck-Engelke U., Donike M. Factors influencing the steroid profile. Recent Advances in Doping Analysis (3) 1995, 95-113. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
35. Bowers L.D. Oral dehydroepiandrosterone supplementation can increase the testosterone/epitestosterone ratio. Clin. Chem. 1999, 45(2):295-297.
36. Dehennin L., Ferry M., Lafarge P., Peres 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 gas chromatography-mass spectrometry. Steroids 1998, 63(2):80-87.
37. Uralets V.P., Gillette P.A. Over-the-counter anabolic steroids 4-androsten-3,17-dione; 4-androsten-3 beta,17 beta-diol; and 19-nor-4-androsten-3,17-dione: excretion studies in men. J. Anal. Toxicol. 1999, 23(5):357-366.
38. Thevis M., Geyer H., Mareck U., Flenker U., Schanzer W. Doping-control analysis of the 5 alpha-reductase inhibitor finasteride: determination of its influence on urinary steroid profiles and detection of its major urinary metabolite. Therap. Drug Monit. 2007, 29(2):236-247.
39. Mareck-Engelke U., Geyer H., Donike M. Stability of steroid profiles. 10th Cologne Workshop on Dope Analysis 1992, 87-89. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke, S. Rauth (Eds.).
40. Mareck-Engelke U., Geyer H., Donike M. Stability of steroid profiles (2): excretion rates from morning urines. Recent Advances in Doping Analysis 1993, 85-185. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke, S. Rauth (Eds.).
41. Mareck-Engelke U., Geyer H., Donike M. Stability of steroid profiles (3): the circadian rhythm of urinary ratios and excretion rates of endogenous steroids in male. Recent Advances in Doping Analysis (2) 1994, 121-1121. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
42. Mareck-Engelke U., Geyer H., Donike M. Stability of steroid profiles (4): ratios and excretion rates of endogenous steroids in female urines collected four times over 24hours. Recent Advances in Doping Analysis (2) 1995, 135-156. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
43. Mareck-Engelke U., Geyer H., Donike M. Stability of steroid profiles (5): the annual rhythm of urinary ratios and excretion rates of endogenous steroids in female and its menstrual dependency. Recent Advances in Doping Analysis (3) 1995, 177-1177. Sport und Buch Strauss, Köln. M. Donike, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
44. Nitschke R. Steroidprofile und Veränderungen biochemischer Parameter bei Hochleistungsradrennfahreren während zwei Rundfahrten 1996, Institute of Biochemistry, German Sport University, Köln.
45. Becchi M., Aguilera R., Farizon Y., Flament M., Casabianca H., James P. Gas chromatography/combustion/isotope-ratio mass spectrometry analysis of urinary steroids to detect misuse of testosterone in sport. Rapid Commun. Mass Spectrom. 1994, 8:304-308.
46. Aguilera R., Becchi M., Grenot C., Casabianca H., Hatton C. Detection of testosterone misuse: comparison of two chromatographic sample preparation methods for gas chromatographic-combustion/isotope ratio mass spectrometric analysis. J. Chromatogr. B 1996, 687:43-53.
47. Aguilera R., Becchi M., Casabianca H., et al. Improved method of detection of testosterone abuse by gas chromatography/combustion/isotope ratio mass spectrometry analysis of urinary steroids. J. Mass Spectrom. 1996, 31:169-176.
48. Shackleton C.H., Phillips A., Chang T., Li Y. Confirming testosterone administration by isotope ratio mass spectrometric analysis of urinary androstanediols. Steroids 1997, 62(4):379-387.
49. Shackleton C.H., 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(10):665-673.
50. Horning S., Geyer H., Gotzmann A., Flenker U., Schänzer W. Detection of exogenous steroids by 13c/12c analysis. Recent Advances in Doping Analysis (6) 1998, 135-148. Sport und Buch Strauss, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
51. Flenker U., Nolteernsting E., Geyer H., Schänzer W. A screening method for synthetic testosterone and its precursors based on gc/c/irms. Recent Advances in Doping Analysis (7) 1999, 241-248. Sport und Buch Strauss, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
52. Saudan C., Baume N., Mangin P., Saugy M. Urinary analysis of 16(5alpha)-androsten-3alpha-ol by gas chromatography/combustion/isotope ratio mass spectrometry: implications in anti-doping analysis. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2004, 810(1):157-164.
53. Cawley A.T., Flenker U. The application of carbon isotope ratio mass spectrometry to doping control. J. Mass Spectrom. 2008, 43(7):854-864.
54. Piper T., Mareck U., Geyer H. Determination of c-13/c-12 ratios of endogenous urinary steroids: method validation, reference population and application to doping control purposes. Rapid Commun. Mass Spectrom. 2008, 22(14):2161-2175.
55. Piper T., Thevis M., Flenker U., Schanzer W. Determination of the deuterium/hydrogen ratio of endogenous urinary steroids for doping control purposes. Rapid Commun. Mass Spectrom. 2009, 23(13):1917-1926.
56. Güntner U., Flenker U., Ayotte C., Ueki M., Schänzer W. D/h-isotope analysis of endogenous steroids-first results. Recent Advances in Doping Analysis (12) 2004, 251-259. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
57. 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" Foren. Sci. Int. 2004, 143(2-3):103-114.
58. Flenker U., Güntner U., Schänzer W. Delta c-13-values of endogenous urinary steroids. Steroids 2008, 73(4):408-416.
59. Ueki M., Okano M. Analysis of exogenous dehydroepiandrosterone excretion in urine by gas chromatography/combustion/isotope ratio mass spectrometry. Rapid Commun. Mass Spectrom. 1999, 13(22):2237-2243.
60. Cawley A.T., Kazlauskas R., Trout G.J., George A.V. Determination of urinary steroid sulfate metabolites using ion paired extraction. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2005, 825(1):1-10.
61. Flenker U., Horning S., Nolteernsting E., Geyer H., Schänzer W. Measurement of 13c/12c-ratios to confirm misuse of endogenous steroids. Recent Advances in Doping Analysis (6) 1999, 243-256. Sport und Buch Strauss, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
62. Tomkins G.M. Enzymatic mechanisms of hormone metabolism. I. Oxidation-reduction of the steroid nucleus. Recent Prog. Horm. Res. 1956, 12:125-133.
63. Schänzer W., Geyer H., Donike M. Metabolism of metandienone 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. 1991, 38(4):441-464.
64. Schänzer W., Delahaut P., Geyer H., Machnik M., Horning S. Long-term detection and identification of metandienone and stanozolol abuse in athletes by gas chromatography high-resolution mass spectrometry. J. Chromatogr. B 1996, 687(1):93-108.
65. Schänzer W., Geyer H., Horning S. 17,17-Dimethyl-18-nor-5α-androst-1,13-dien-3α-ol (18-normetenol) in longterm detection and confirmation of positive metandienone cases. Recent Advances in Doping Analysis (6) 1999, 37-52. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck-Engelke (Eds.).
66. Schänzer W., Geyer H., Fußhoeller H., Halatcheva N., Kohler M., Parr M., Guddat S., Thomas A., Thevis M. Mass spectrometric identification and characterization of a new long-term metabolite of metandienone in human urine. Rapid Commun. Mass Spectrom. 2006, 20:2252-2258.
67. Kuuranne T., Pystynen K.H., Thevis M., Leinonen A., Schanzer W., Kostiainen R. Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry. Eur. J. Mass Spectrom. (Chichester, Eng.) 2008, 14(3):181-189.
68. Hintikka L., Kuuranne T., Leinonen A., Thevis M., Schanzer W., Halket J., Cowan D., Grosse J., Hemmersbach P., Nielen M.W., Kostiainen R. Liquid chromatographic-mass spectrometric analysis of glucuronide-conjugated anabolic steroid metabolites: method validation and interlaboratory comparison. J. Mass Spectrom. 2008, 43(7):965-973.
69. Kuuranne T., Kotiaho T., Pedersen-Bjergaard S., Einar Rasmussen K., Leinonen A., Westwood S., Kostiainen R. Feasibility of a liquid-phase microextraction sample clean-up and liquid chromatographic/mass spectrometric screening method for selected anabolic steroid glucuronides in biological samples. J. Mass Spectrom. 2003, 38(1):16-26.
70. Pozo O.J., Van Eenoo P., Van Thuyne W., Deventer K., Delbeke F.T. Direct quantification of steroid glucuronides in human urine by liquid chromatography-electrospray tandem mass spectrometry. J. Chromatogr. A 2008, 1183(1-2):108-118.
71. World Anti-Doping Agency, Wada technical document td2009mrpl, 2008, online at , 31 July 2009. http://www.wada-ama.org/rtecontent/document/MINIMUM_REQUIRED_PERFORMANCE_LEVELS_TD_v1_0_January_2009.pdf.
72. Piper T., Hebestreit M., Flenker U., Geyer H., Schänzer W. A new method to determine d13cvpdb-values of trace amounts of boldenone and its main metabolite. Recent Advances in Doping Analysis (15) 2007, 169-178. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
73. Ayotte C. Significance of 19-norandrosterone in athletes' urine samples. Br. J. Sports Med. 2006, 40(Suppl 1):i25-i29.
74. Dehennin L., Jondet M., Scholler R. Androgen and 19-norsteroid profiles in human preovulatory follicles from stimulated cycles: an isotope dilution-mass spectrometric study. J. Steroid Biochem. 1987, 26(3):399-405.
75. Van Eenoo P., Delbeke F.T., de Jong F.H., De Backer P. Endogenous origin of norandrosterone in female urine: indirect evidence for the production of 19-norsteroids as by-products in the conversion from androgen to estrogen. J. Steroid Biochem. Mol. Biol. 2001, 78(4):351-357.
76. Reznik Y., Herrou M., Dehennin L., Lemaire M., Leymarie P. Rising plasma levels of 19-nortestosterone throughout pregnancy: determination by radioimmunoassay and validation by gas chromatography-mass spectrometry. J. Clin. Endocrinol. Metab. 1987, 64(5):1086-1088.
77. Grosse J., Anielski P., Hemmersbach P., Lund H., Mueller R.K., Rautenberg C., Thieme D. Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids 2005, 70(8):499-506.
78. World Anti-Doping Agency, Wada technical document td2004na, 2004, online at , 31 July 2009. http://www.wada-ama.org/rtecontent/document/nandrolone_aug_04.pdf.
79. Zierau O., Lehmann S., Vollmer G., Schanzer W., Diel P. Detection of anabolic steroid abuse using a yeast transactivation system. Steroids 2008, 73(11):1143-1147.
80. Nielen M.W., van Engelen M.C., Zuiderent R., Ramaker R. Screening and confirmation criteria for hormone residue analysis using liquid chromatography accurate mass time-of-flight, fourier transform ion cyclotron resonance and orbitrap mass spectrometry techniques. Anal. Chim. Acta 2007, 586(1-2):122-129.
81. Catlin D.H., Ahrens B.D., Kucherova Y. Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine. Rapid Commun. Mass Spectrom. 2002, 16(13):1273-1275.
82. Knight J. Drugs bust reveals athletes' secret steroid. Nature 2003, 425(6960):752-1752.
83. Catlin D.H., Sekera M.H., Ahrens B.D., Starcevic B., Chang Y.C., Hatton C.K. Tetrahydrogestrinone: discovery, synthesis, and detection in urine. Rapid Commun. Mass Spectrom. 2004, 18(12):1245-1249.
84. Sekera M.H., Ahrens B.D., Chang Y.C., Starcevic B., Georgakopoulos C., Catlin D.H. Another designer steroid: discovery, synthesis, and detection of 'madol' in urine. Rapid Commun. Mass Spectrom. 2005, 19(6):781-784.
85. California USAftNDo, Chemist who created " the clear" sentenced, Press release, 2006, online at , 28 October 2007. http://www.usdoj.gov/usao/can/press/2006/2006_08_04_arnold_sentencing%2520press.htm.
86. US Drug Enforcement Administration, Anabolic steroids control act, 2004, online at , 31 October 2005. http://frwebgate.access.gpo.gov/cgi-bin/getdoc.cgi%3Fdbname=108_cong_bills%20%26docid=f%3Ah3866rfs.txt.pdf.
87. Parr M., Geyer H., Opfermann G., Schänzer W. Prescription drugs and new anabolic steroids in nutritional supplements. Recent Advances in Doping Analysis (12) 2004, 71-80. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
88. Parr M., Opfermann G., Schänzer W. Analytical properties of 4-hydroxysteroids and some esters. Recent Advances in Doping Analysis (12) 2004, 129-139. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
89. Van Eenoo P., Mikulèíková P., Deventer K., VanThuyne W., Delbeke F. Metabolism, excretion and detection of androst-4-ene-3,6,17-trione. Recent Advances in Doping Analysis (13) 2005, 57-64. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
90. Van Eenoo P., Delbeke F.T. Metabolism and excretion of anabolic steroids in doping control-new steroids and new insights. J. Steroid Biochem. Mol. Biol. 2006, 101(4-5):161-178.
91. Parr M.K., Opfermann G., Schänzer W. Detection of new 17-alkylated anabolic steroids on wada 2006 list. Recent Advances in Doping Analysis (14) 2006, 249-258. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
92. Rodchenkov G., Sobolevsky T., Sizoi V. New designer anabolic steroids from internet. Recent Advances in Doping Analysis (14) 2006, 141-150. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
93. Kazlauskas R. Miscellaneous projects in sports drug testing at the national measurement institute, Australia, 2005. Recent Advances in Doping Analysis (14) 2006, 129-140. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
94. Parr M.K., Opfermann G., Piper T., Schlörer N., Fußhöller G., Thomas A., Thevis M., Schänzer W. Characterisation of steroid metabolites recently detected in doping control analyses. Recent Advances in Doping Analysis (15) 2007, 143-152. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
95. Kohler M., Parr M.K., Opfermann G., Thevis M., Schlorer N., Marner F.J., Schanzer W. Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: mass spectrometric identification of urinary metabolites. Steroids 2007, 72(3):278-286.
96. Kazlauskas R. Supplements & wada list. Recent Advances in Doping Analysis (15) 2007, 31-40. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
97. Parr M.K., Geyer H., Gütschow M., Haenelt N., Opfermann G., Piper T., Thevis M., Schänzer W. New steroids on the " supplement" market. Recent Advances in Doping Analysis (16) 2008, 73-82. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
98. Parr M.K., Kazlauskas R., Schlorer N., Opfermann G., Piper T., Schulze G., Schanzer W. 6 alpha-methylandrostenedione: gas chromatographic mass spectrometric detection in doping control. Rapid Commun. Mass Spectrom. 2008, 22(3):321-329.
99. Sobolevsky T., Virus E., Semenistaya E., Kachala V., Kachala I., Rodchenkov G. Orastan-a: structural elucidation and detection in urine. Recent Advances in Doping Analysis (16) 2008, 337-340. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
100. Parr M.K., Fußhöller G., Schlörer N., Opfermann G., Piper T., Rodchenkov G., 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. 2009, 23(2):207-218.
101. L. Brooker, M.K. Parr, A. Cawley, U. Flenker, C. Howe, R. Kazlauskas, W. Schänzer, A. George, Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control, Drug Test. Anal., in press. doi:10.1002/dta.108.
102. Parr M.K., Gutschow M., Daniels J., Opfermann G., Thevis M., Schanzer W. Identification of steroid isoxazole isomers marketed as designer supplement. Steroids 2009, 74(3):322-328.
103. Parr M.K., Haenelt N., Fußhöller G., Flenker U., Rodchenkov G., Opfermann G., Schänzer W. Recent steroid findings in " designer supplements" Cologne Workshop on Dope Analysis 2009.
104. Vida J.A. Androgens and Anabolic Agents 1969, Academic Press, New York and London.
105. Thevis M., Schanzer W. Mass spectrometry in sports drug testing: structure characterization and analytical assays. Mass Spectrom. Rev. 2007, 26(1):79-107.
106. Thevis M., Geyer H., Mareck U., Schänzer W. Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. J. Mass Spectrom. 2005, 40(7):955-962.
107. Pozo O.J., Deventer K., Eenoo P.V., Delbeke F.T. Efficient approach for the comprehensive detection of unknown anabolic steroids and metabolites in human urine by liquid chromatography-electrospray-tandem mass spectrometry. Anal. Chem. 2008, 80(5):1709-1720.
108. Mokbel K. The evolving role of aromatase inhibitors in breast cancer. Int. J. Clin. Oncol. 2002, 7(5):279-283.
109. Motta M., Zoppi S., Brodie A.M., Martini L. Effect of 1,4,6-androstatriene-3,17-dione (atd), 4-hydroxy-4-androstene-3,17-dione (4-oh-a) and 4-acetoxy-4-androstene-3,17-dione (4-ac-a) on the 5 alpha-reduction of androgens in the rat prostate. J. Steroid Biochem. Mol. Biol. 1986, 25(4):593-600.
110. Leder B.Z., Rohrer J.L., Rubin S.D., Gallo J., Longcope C. Effects of aromatase inhibition in elderly men with low or borderline-low serum testosterone levels. J. Clin. Endocrinol. Metab. 2004, 89(3):1174-1180.
111. Van Thuyne W., Van Eenoo P., Mikulcikova P., Deventer K., Delbeke F.T. Detection of androst-4-ene-3,6,17-trione (6-oxo) and its metabolites in urine by gas chromatography-mass spectrometry in relation to doping analysis. Biomed. Chromatogr. 2005, 19(9):689-695.
112. Fechner S., Husen B., Thole H., Schmidt M., Gashaw I., Kimmig R., Winterhager E., Grummer R. Expression and regulation of estrogen-converting enzymes in ectopic human endometrial tissue. Fertil. Steril. 2007, 88(4 Suppl):1029-1038.
113. Reynolds J.E.F. Martindale-The Extra Pharmacopeia 1993, Royal Pharmaceutical Society, London.
114. Polettini A., Marrubini Bouland G., Montagna M. Development of a coupled-column liquid chromatographic-tandem mass spectrometric method for the direct determination of betamethasone in urine. J. Chromatogr. B: Biomed. Sci. Appl. 1998, 713(2):339-352.
115. Wang Y., Tang Y., Moellmann H., Hochhaus G. Simultaneous quantification of budesonide and its two metabolites, 6beta-hydroxybudesonide and 16alpha-hydroxyprednisolone, in human plasma by liquid chromatography negative electrospray ionization tandem mass spectrometry. Biomed. Chromatogr. 2003, 17(2-3):158-164.
116. Rang H., Ritter L., Dale M. Pharmacology 1995, Churchill Livingstone, New York.
117. Mazzarino M., de la Torre X., Botre F. A screening method for the simultaneous detection of glucocorticoids, diuretics, stimulants, anti-oestrogens, beta-adrenergic drugs and anabolic steroids in human urine by LC-ESI-MS/MS. Anal. Bioanal. Chem. 2008, 392(4):681-698.
118. Deventer K., Delbeke F.T. Validation of a screening method for corticosteroids in doping analysis by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2003, 17(18):2107-2114.
119. Gotzmann A., Thevis M., Mareck U., Bredehöft M., Guddat S., Schänzer W. LC-MS/MS analysis of glucocorticosteroids: first experiences with therapeutic use exemption in routine doping analysis. Recent Advances in Doping Analysis (12) 2004, 55-63. Sport und Buch Strauß, Köln. W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck (Eds.).
120. Touber M.E., van Engelen M.C., Georgakopoulus C., van Rhijn J.A., Nielen M.W. Multi-detection of corticosteroids in sports doping and veterinary control using high-resolution liquid chromatography/time-of-flight mass spectrometry. Anal. Chim. Acta 2007, 586(1-2):137-146.
121. Mazzarino M., Turi S., Botre F. A screening method for the detection of synthetic glucocorticosteroids in human urine by liquid chromatography-mass spectrometry based on class-characteristic fragmentation pathways. Anal. Bioanal. Chem. 2008, 390(5):1389-1402.
122. Schänzer W., Gotzmann A., Horning S., Donike M. Trimethylsilyl derivatisation of endogenous and synthetic corticosteroids for GC/MS identification. Proceedings 10th Int. Conference of Racing Analysts and Veterinarians 1994, 140-145. R&W Publications, Newmarket. E. Houghton (Ed.).
123. Yap B.K., Johnston G.A., Kazlauskas R. Routine screening and quantitation of urinary corticosteroids using bench-top gas chromatography-mass-selective detection. J. Chromatogr. 1992, 573(2):183-190.
124. McLaughlin L.G., Henion J.D. Determination of dexamethasone in bovine tissues by coupled-column normal-phase high-performance liquid chromatography and capillary gas chromatography-mass spectrometry. J. Chromatogr. 1990, 529(1):1-19.
125. Rubin M.R., Bilezikian J.P. New anabolic therapies in osteoporosis. Endocrinol. Metab. Clin. North Am. 2003, 32(1):285-307.
126. Markiewicz L., Gurpide E. Invitro evaluation of estrogenic, estrogen antagonistic and progestagenic effects of a steroidal drug (org od-14) and its metabolites on human endometrium. J. Steroid Biochem. Mol. Biol. 1990, 35(5):535-541.
127. Raobaikady B., Parsons M.F.C., Reed M.J., Purohit A. Lack of aromatisation of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative. Steroids 2006, 71(7):639-646.
128. Lisi A.M., Trout G.J., Kazlauskas R. Screening for diuretics in human urine by gas chromatography-mass spectrometry with derivatisation by direct extractive alkylation. J. Chromatogr. 1991, 563(2):257-270.
129. Ventura R., Fraisse D., Becchi M., Paisse O., Segura J. Approach to the analysis of diuretics and masking agents by high-performance liquid chromatography-mass spectrometry in doping control. J. Chromatogr. 1991, 562(1-2):723-736.
130. Thieme D., Grosse J., Lang R., Mueller R.K., Wahl A. Screening, confirmation and quantification of diuretics in urine for doping control analysis by high-performance liquid chromatography-atmospheric pressure ionisation tandem mass spectrometry. J. Chromatogr. B: Biomed. Sci. Appl. 2001, 757(1):49-57.
131. Deventer K., Delbeke F.T., Roels K., Van Eenoo P. Screening for 18 diuretics and probenecid in doping analysis by liquid chromatography-tandem mass spectrometry. Biomed. Chromatogr. 2002, 16(8):529-535.
132. Beyer J., Bierl A., Peters F.T., Maurer H.H. Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation. Therap. Drug Monit. 2005, 27(4):509-520.