Impact of the emergence of designer drugs upon sports doping testing

Bioanalysis

Volumn 4, Issue 1, 2012, Pages 71-88

  Teale, P ^a   Scarth, J ^a   Hudson, S ^a  

^a LGC   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 ANDOSTERONE; 17 ALPHA METHYLDROSTANOLONE; 4 CHLORO 17 ALPHA METHYLANDROST 4 ENE 3,17 BETA DIOL; 4 CHLORO 17 ALPHA METHYLANDROSTA 1,4 DIENE 3,17 BETA DIOL; 4 CHLORO 17BETA HYDROXY 17 METHYLANDROSTA 1,4 DIEN 3 ONE; 4,9 ESTRADIENE 3,17 DIONE; 6 ALPHA METHYLANDROST 4 ENE 3,20 DIONE; ANABOLIC AGENT; ANDROSTA 1,4,6 TRIENE 3,17 DIONE; BIOLOGICAL MARKER; DESIGNER DRUG; METHASTERONE; METHYLTESTOSTERONE; TETRAHYDROGESTRINONE; UNCLASSIFIED DRUG;

BIOASSAY; CHEMICAL STRUCTURE; DOPING; DRUG DETERMINATION; DRUG METABOLISM; HUMAN; IMMUNOASSAY; MASS SPECTROMETRY; NONHUMAN; RECREATION; REVIEW; STEROID METABOLISM;

ANIMALS; DESIGNER DRUGS; DOPING IN SPORTS; HUMANS; SUBSTANCE ABUSE DETECTION;

EID: 84555190749     PISSN: 17576180     EISSN: 17576199     Source Type: Journal    
DOI: 10.4155/bio.11.291     Document Type: Review

References (177)

1. Müller RK. History of doping and doping control. In: Handbook of Experimental Pharmacology. Doping in Sports. Thieme D, Hemmersbach P (Eds). Springer, Heidelberg, Germany, 195, 1-23 (2010).
2. Bowers LD. The analytical chemistry of drug monitoring in athletes. Ann. Rev. Anal. Chem. 2, 485-507 (2009).
3. Basaria S. Androgen abuse in athletes: detection and consequences. J. Clin. Endocrinol. Metab. 95(4), 1533-1543 (2010).
4. ® (methasteron): a case report and literature review. Dig. Dis. Sci. 54(5), 1144-1146 (2009).
5. Botrè F, Pavan A. Enhancement drugs and the athlete. Neurol. Clin. 26(1), 149-167 (2008). (Pubitemid 351265389)
6. Hanstad DV, Waddington I. Sport, health and drugs: a critical re-examination of some key issues and problems. Perspect. Public Health. 129(4), 174-182 (2009).
7. Thevis M, Schänzer W. Mass spectrometry in sports drug-testing: structure characterization and analytical assays. Mass Spectrom. Rev. 26(1), 79-107 (2007). (Pubitemid 46051814)
8. Thevis M, Schänzer W. Current role of LC-MS/MS in doping control. Anal. Bioanal. Chem. 288, 1351-1458 (2007).
9. Thevis M. Mass Spectrometry in Sports Drug Testing: Characterization of Prohibited Substances and Doping Control Analytical Assays. Desiderio DM, Nibbering HM (Eds). John Wiley and Sons Ltd, Hoboken, USA (2010).
10. Thevis M, Thomas A, Schänzer W. Current role of LC-MS/MS in doping control. Anal. Bioanal. Chem. 401(2), 405-420 (2011).
11. McKinney AR. Modern techniques for the determination of anabolic androgenic steroid doping in the horse. Bioanalysis 1(4), 785-803 (2009).
12. Catlin DH, Fitch KD, Ljungqvist A. Medicine and science in the fght against doping in sport. J. Intern. Med. 264, 99-114 (2008). (Pubitemid 351962580)
13. Fitch KD. Androgenic-anabolic steroids and the Olympic Games. Asian J. Androl. 10(3), 384-390 (2008). (Pubitemid 351584114)
14. Striegel H, Simon P. Doping: high-tech cheating in sport. Internist. 48(7), 737-742 (2007).
15. Graham MR, Davies B, Grace FM, Kicman A, Baker JS. Anabolic steroid use: patterns of use and detection of doping. Sports Med. 38(6), 505-525 (2008). (Pubitemid 351704855)
16. Hemmersbach P. History of mass spectrometry at the Olympic Games. J. Mass Spectrom. 43(7), 839-853 (2008). (Pubitemid 352035817)
17. Strano-Rossi S, Fiore C, Chiarotti M, Centini F. Analytical techniques in androgen anabolic steroids (AASs) analysis for antidoping and forensic purposes. Mini Rev. Med. Chem. 11(5), 451-458 (2011).
18. Thevis M, Kuuranne T, Geyer H, Schänzer W Annual banned-Substance review: the prohibited list 2008-analytical approaches in human sports drug-testing. Drug Test. Anal. 1(1), 4-13 (2009).
19. Thevis M, Kuuranne T, Geyer H, Schänzer W Annual banned-substance review: analytical approaches in human sports drug-testing. Drug Test. Anal. 2(4), 149-161 (2010).
20. Thevis M, Kuuranne T, Geyer H, SchänzerW. Annual banned-substance review: analytical approaches in human sports drug-testing. Drug Test. Anal. 3(1), 1-14 (2011).
21. Thevis M, Thomas A, Kohler M et al. Mass spectro me try-based characterization of new drugs and methods of performance manipulation in doping control analysis. Eur. J. Mass Spectrom. 16(3), 301-312 (2010).
22. Thevis M, Geyer H, Thomas A, Schänzer W. Traffcking of drug candidates relevant for sports drug-testing: detection of non-approved therapeutics categorized as anabolic and gene doping agents in products distributed via the internet. Drug Test. Anal. 3(5), 331-336 (2011).
23. Möller I, Thomas A, Geyer H, Schänzer W, Thevis M. Synthesis, characterization, and mass spectrometric detection of a PEGylated EPO-mimetic peptide for sports drug-testing purposes. Rapid Commun. Mass Spectrom. 25(15), 2115-2123 (2011).
24. Beuck S, Schänzer W, Thevis M. Investigation of the in vitro metabolism of the emerging drug candidate S107 for doping-preventive purposes. J. Mass Spectrom. 46(2), 112-130 (2011).
25. Thevis M, Kohler M, Schänzer W New drugs and methods of doping and manipulation. Drug Discov. Today 13(1-2), 59-66 (2008).
26. Kazlauskas R. Designer Steroids In: Handbook of Experimental Pharmacology. Doping in Sports. Thieme D, Hemmersbach P (Eds). Springer, Heidelberg, Germany, 195, 155-185 (2010).
27. Catlin DH, Sekera MH, Ahrens BD, Starcevic B, Chang YC, Hatton CK. Tetrahydrogestrinone: discovery, synthesis and detection in urine. Rapid Commun. Mass Spectrom. 18, 1245-1249 (2004). (Pubitemid 38843145)
28. Kicman AT Pharmacology of anabolic steroids Br. J. Pharmacol. 154, 502-521 (2008). (Pubitemid 351744954)
29. Peters FT, Martinez-Ramirez JA. Analytical toxicology of emerging drugs of abuse. Ther. Drug Monit. 32(5), 532-539 (2010).
30. Wissenbach DK, Meyer MR, Remane D, Philipp AA, Weber AA, Maurer HH. Drugs of abuse screening in urine as part of a metabolite-based LC-MS(n) screening concept. Anal. Bioanal. Chem. 400(10), 3481-3489 (2011).
31. Maurer HH, Kraemer T, Springer D, Staack RF. Chemistry, pharmacology, toxicology and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine and pyrrolidinophenone types: a synopsis. Ther. Drug Monit. 26(2), 127-131 (2004). (Pubitemid 38501205)
32. Maurer HH. Chemistry, pharmacology and metabolism of emerging drugs of abuse. Ther. Drug Monit. 32(5), 544-549 (2010).
33. Staack RF, Maurer HH. Metabolism of designer drugs of abuse. Curr. Drug Metab. 6(3), 259-274 (2005). (Pubitemid 40753856)
34. Staack RF, Springer D, Theobald DS, Maurer HH. New designer drugs. Pharmacology, toxicology and metabolism. Med. Monatsschr. Pharm. 27(12), 408-413 (2004). (Pubitemid 39664456)
35. Staack RF. Piperazine designer drugs of abuse. Lancet 369(9571), 1411-1413 (2007). (Pubitemid 46646952)
36. Wohlfarth A, Weinmann W. Bioanalysis of new designer drugs. Bioanalysis 2(5), 965-979 (2010).
37. Meyer MR, Maurer HH. Metabolism of designer drugs of abuse: an updated review. Curr. Drug Metab. 11(5), 468-482 (2010).
38. Kelly JP. Cathinone derivatives: a review of their chemistry, pharmacology and toxicology Drug Test. Anal. 3(7-8), 439-453 (2011).
39. Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA. Aminoindanes-the next wave of 'legal highs'? Drug Test. Anal. 3(7-8), 479-482 (2011).
40. Collins M. Some new psychoactive substances: precursor chemicals and synthesis-driven end-products. Drug Test. Anal. 3(7-8), 404-416 (2011).
41. Vardakou I, Pistos C, Spiliopoulou CH. Spice drugs as a new trend: mode of action, identifcation and legislation. Toxicol. Lett. 197(3), 157-162 (2010).
42. Dargan PI, Hudson S, Ramsey J, Wood DM. The impact of changes in UK classifcation of the synthetic cannabinoid receptor agonists in 'Spice'. Int. J. Drug Policy 22(4), 274-277 (2011).
43. Dresen S, Kneisel S, Weinmann W, Zimmermann R, Auwärter V Development and validation of a liquid chromatography-tandem mass spectrometry method for the quantitation of synthetic cannabinoids of the aminoalkylindole type and methanandamide in serum and its application to forensic samples. J. Mass Spectrom. 46(2), 163-171 (2011).
44. Hudson S, Ramsey J. The emergence and analysis of synthetic cannabinoids. Drug Test. Anal. 3(7-8), 466-478 (2011).
45. Venhuis BJ, Zomer G, Hamzink M, Meiring HD, Aubin Y, de Kaste D. The identifcation of a nitrosated prodrug of the PDE-5 inhibitor aildenafl in a dietary SUPPL.ement: a Viagra with a pop. J. Pharm. Biomed. Anal. 54(4), 735-741 (2011).
46. Venhuis BJ, Blok-Tip L, de Kaste D. Designer drugs in herbal aphrodisiacs. Forensic Sci. Int. 177(2-3), 25-27 (2008).
47. Reepmeyer JC, Woodruff JT, d'Avignon DA. Structure elucidation of a novel analogue of sildenafl detected as an adulterant in an herbal dietary SUPPL.ement. J. Pharm. Biomed. Anal. 43(5), 1615-1621 (2007). (Pubitemid 46464006)
48. Gratz SR, Gamble BM, Flurer RA. Accurate mass measurement using Fourier transform ion cyclotron resonance mass spectrometry for structure elucidation of designer-drug analogs of tadalafl, vardenafl and sildenafl in herbal and pharmaceutical matrices. Rapid Commun. Mass Spectrom. 20(15), 2317-2327 (2006). (Pubitemid 44199623)
49. Houghton E, Maynard S. Some aspects of doping and medication control in equine sports. In: Handbook of Experimental Pharmacology. Doping in Sports. Thieme D, Hemmersbach P (Eds). Springer, Heidelberg, Germany, 195, 369-409 (2010).
50. Scarth JP, Teale P, Kuuranne T. Drug metabolism in the horse: a review. Drug Test. Anal. 3(1), 19-53 (2010).
51. Scarth J, Clarke A, Teale P, Pearce C. Comparative in vitro metabolism of the designer-drug estra-4,9-diene-3,17-dione between the equine, canine and human: identifcation of target metabolites for use in sports doping control. Steroids 75, 643-652 (2010).
52. Clarke A, Scarth J, Teale P, Pearce C, Hillyer L. The use of in vitro technologies and high-re solution/accurate-mass LC-MS to screen for metabolites of 'designer' steroids in the equine. Drug Test. Anal. 3(1), 74-87 (2011).
53. Hudson, Ramsey J, King L et al. Use of high-resolution accurate mass spectrometry to detect reported and previously unreported cannabinomimetics in 'herbal high' products. J. Anal. Toxicol. 34(5), 252-260 (2010).
54. Peters RJ, van Engelen MC, Touber ME, Georgakopoulus C, Nielen MW. Searching for in silico predicted metabolites and designer modifcations of (cortico)steroids in urine by high-resolution liquid chromatography-time-of- fight mass spectrometry. Rapid Commun. Mass Spectrom. 23(15), 2329-2337 (2009).
55. Ungerleider S. Steroids: youth at risk. Harv. Ment. Health Lett. 17(11), 4-5 (2001).
56. Sekera MH, Ahrens BD, Chang YC, Starcevic B, Georgakopoulos C, Catlin DH. Another designer steroid: discovery, synthesis, and detection of 'madol' in urine. Rapid Commun. Mass Spectrom. 19(6), 781-784 (2005). (Pubitemid 40349418)
57. Catlin DH, Ahrens BD, Kucherova Y. Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine. Rapid Commun. Mass Spectrom. 16(13), 1273-1275 (2002). (Pubitemid 34717253)
58. Mareck U, Geyer H, Opfermann G, Thevis M, Schänzer W. Factors infuencing the steroid profle in doping control analysis. J. Mass Spectrom. 43(7), 877-891 (2008). (Pubitemid 352029656)
59. Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C. Schemes of metabolic patterns of anabolic androgenic steroids for the estimation of metabolites of designer steroids in human urine. J. Steroid Biochem. Mol. Biol. 115(1-2), 44-61 (2009).
60. Thevis M, Bommerich U, Opfermann G, Schänzer W. Characterization of chemically modifed steroids for doping control purposes by electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 40(4), 494-502 (2005). (Pubitemid 40637873)
61. 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. 40(7), 955-962 (2005). (Pubitemid 41098082)
62. Thevis M, Schänzer W Synthetic anabolic agents: steroids and nonsteroidal selective androgen receptor modulators. In: Handbook of Experimental Pharmacology. Doping in Sports. Thieme D, Hemmersbach P (Eds). Springer, Heidelberg, Germany, 195, 99-126 (2010).
63. Thevis M, Thomas A, Möller I, Geyer H, Dalton JT, Schänzer W Mass spectrometric characterization of urinary metabolites of the selective androgen receptor modulator S-22 to identify potential targets for routine doping controls. Rapid Commun. Mass Spectrom. 25(15), 2187-2195 (2011).
64. Gerace E, Salomone A, Fasano F et al. Validation of a GC-MS method for the detection of two quinolinone-derived selective androgen receptor modulators in doping control analysis. Anal. Bioanal. Chem. 400(1), 137-144 (2011).
65. Thevis M, Geyer H, Kamber M, Schänzer W Detection of the arylpropionamide-derived selective androgen receptor modulator (SARM) S-4 (Andarine) in a black-market product. Drug Test. Anal. 1(8), 387-392 (2009).
66. Parr MK, Opfermann G, Geyer H et al. Seized designer SUPPL.ement named '1-androsterone': identifcation as 3b-hydroxy-5a-androst-1-en-17-one and its urinary elimination. Steroids 76(6), 540-547 (2011).
67. Parr MK, Gütschow M, Daniels J, Opfermann G, Thevis M, Schänzer W. Identifcation of steroid isoxazole isomers marketed as designer SUPPL.ement. Steroids 74(3), 322-328 (2008).
68. Parr MK, Fusshöller G, Schlörer N et al. Detection of D6-methyltestosterone in a 'dietary SUPPL.ement' and GC-MS/MS investigations on its urinary metabolism. Toxicol. Lett. 201(2), 101-104 (2010).
69. Parr MK, Schänzer W Detection of the misuse of steroids in doping control. J. Steroid Biochem. Mol. Biol. 121(3-5), 528-537 (2010).
70. Parr MK, Fusshöller G, Schlörer N et al. 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(2), 207-218 (2009).
71. Okano M, Sato M, Ikekita A, Kageyama S. Analysis of non-ketoic steroids 17a-methylepithiostanol and desoxymethyl-testosterone in dietary SUPPL.ements. Drug Test. Anal. 1(11-12), 518-525 (2009).
72. Kohler M, Thomas A, Geyer H, Petrou M, Schänzer W, Thevis M. Confscated black market products and nutritional SUPPL.ements with non-approved ingredients analyzed in the Cologne Doping Control Laboratory 2009. Drug Test. Anal. 2(11-12), 533-537 (2010).
73. Cordaro FG, Lombardo S, Cosentino M. Selling androgenic anabolic steroids by the pound: identifcation and analysis of popular websites on the internet. Scand. J. Med. Sci. Sports doi:10.1111/j.1600-0838.2010.01263.x (2011) (Epub ahead of print).
74. Thevis M, Schänzer W. Mass spectrometry of selective androgen receptor modulators. J. Mass Spectrom. 43(7), 865-876 (2008). (Pubitemid 352029655)
75. Ewald AH, Maurer HH. 2,5-dimethoxyamphetamine-derived designer drugs: studies on the identifcation of cytochrome P450 (CYP) isoenzymes involved in formation of their main metabolites and on their capability to inhibit CYP2D6. Toxicol. Lett. 183(1-3), 52-57 (2008).
76. Uchiyama N, Kikura-Hanajiri R, Ogata J, Goda Y. Chemical analysis of synthetic cannabinoids as designer drugs in herbal products. Forensic Sci. Int. 198(1-3), 31-38 (2010).
77. Peters FT, Meyer MR. In vitro approaches to studying the metabolism of new psychoactive compounds. Drug Test. Anal. 3(7-8), 483-495 (2011).
78. Baron M, Elie M, Elie L. An analysis of legal highs-do they contain what it says on the tin? Drug Test. Anal. 3(9), 576-581 (2011).
79. Fragkaki AG, Angelis YS, Tsantili-Kakoulidou A, Koupparis M, Georgakopoulos C. Statistical analysis of fragmentation patterns of electron ionization mass spectra of enolized-trimethylsilylated anabolic androgenic steroids. Int. J. Mass Spectrom. 285(1-2), 58-69 (2009).
80. Pozo OJ, Deventer K, Eenoo PV, Delbeke FT. Effcient approach for the comprehensive detection of unknown anabolic steroids and metabolites in human urine by liquid chromatography-electrospray-tandem mass spectrometry. Anal. Chem. 80, 1709-1720 (2008). (Pubitemid 351429577)
81. Pozo OJ, Van Eenoo P, Deventer K et al. Collision-induced dissociation of 3-keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation. Rapid Commun. Mass Spectrom. 22, 4009-4024 (2008).
82. Guan F, Soma LR, Luo Y, Uboh CE, Peterman S. Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 17, 477-489 (2006).
83. Pelander A, Tyrkkö E, Ojanperä I. In silico methods for predicting metabolism and mass fragmentation applied to quetiapine in liquid chromatography-time-of-fight mass spectrometry urine drug screening. Rapid Commun. Mass Spectrom. 23(4), 506-514 (2009).
84. Tyrkkö E, Pelander A, Ojanperä I. Differentiation of structural isomers in a target drug database by LC-Q-TOFMS using fragmentation prediction. Drug Test. Anal. 2, 259-270 (2010).
85. Fragkaki AG, Tsantili-Kakoulidou A, Angelis YS, Koupparis M, Georgakopoulos C. Gas chromatographic quantitative structure-retention relationships of trimethylsilylated anabolic androgenic steroids by multiple linear regression and partial least squares. J. Chromatogr. A 1216(47), 8404-8420 (2009).
86. Van Eenoo P, Van Gansbeke W, De Brabanter N, Deventer K, Delbeke FT. A fast, comprehensive screening method for doping agents in urine by gas chromatography-triple-quadrupole mass spectrometry. J. Chromatogr. A 1218(21), 3306-3316. (2010).
87. Revelsky AI, Samokhin AS, Virus ED, Rodchenkov GM, Revelsky IA. High sensitive analysis of steroids in doping control using gas chromatography-time- of-fight mass spectrometry. Drug Test. Anal. 3(4), 263-267 (2011).
88. Van Poucke C, Detavernier C, Van Cauwenberghe R, Van Peteghem C. Determination of anabolic steroids in dietary SUPPL.ements by liquid chromatography-tandem mass spectrometry. Anal. Chim. Acta 586(1-2), 35-42 (2007). (Pubitemid 46240018)
89. Nielen MW, Bovee TF, van Engelen MC et al. Urine testing for designer steroids by liquid chromatography with androgen bioassay detection and electrospray quadrupole time-of-fight mass spectrometry identifcation. Anal. Chem. 78(2), 424-431 (2006). (Pubitemid 43100373)
90. Georgakopoulos CG, Vonaparti A, Stamou M et al. Preventive doping control analysis: liquid and gas chromatography time-of-fight mass spectrometry for detection of designer Steroids Rapid Commun. Mass Spectrom. 21 (15), 2439-2446 (2007). (Pubitemid 47203270)
91. Peters RJB, Oosterink JE, Stolker AAM, Georgakopoulos C, Nielen MWF. Generic sample preparation combined with high-resolution liquid chromatography-time-of-fight mass spectrometry for unifcation of urine screening in doping-control laboratories. Anal. Bioanal. Chem. 396(7), 2583-2598 (2010).
92. van der Heeft E, Bolck YJ, Beumer B, Nijrolder AW, Stolker AA, Nielen MW. Full-scan accurate mass selectivity of ultra-performance liquid chromatography combined with time-of-fight and Orbitrap mass spectrometry in hormone and veterinary drug residue analysis. J. Am. Soc. Mass Spectrom. 20(3), 451-463 (2009).
93. Becue I, Van Poucke C, Van Peteghem C. An LC-MS screening method with library identifcation for the detection of steroids in dietary SUPPL.ements. J. Mass Spectrom. 46(3), 327-335 (2011).
94. Nielen MW, van Engelen MC, Zuiderent R, Ramaker R. Screening and confrmation criteria for hormone residue analysis using liquid chromatography accurate mass time-of-fight, Fourier transform ion cyclotron resonance and Orbitrap mass spectrometry techniques. Anal. Chim. Acta 586(1-2), 122-129 (2006).
95. Peters RJ, Bolck YJ, Rutgers P, Stolker AA, Nielen MW. Multi-residue screening of veterinary drugs in egg, fsh and meat using high-resolution liquid chromatography accurate mass time-of-fight mass spectrometry. J. Chromatogr. A 1216(46), 8206-8216 (2009).
96. Vonaparti A, Lyris E, Angelis YS et al. Preventive doping control screening analysis of prohibited substances in human urine using rapid-resolution liquid chromatography-high-resolution time-of-fight mass spectrometry. Rapid Commun. Mass Spectrom. 24(11), 1595-1609 (2010).
97. Kolmonen M, Leinonen A, Kuuranne T, Pelander A, Ojanperä I. Generic sample preparation and dual polarity liquid chromatography-time-of-fight mass spectrometry for high-throughput screening in doping analysis. Drug Test. Anal. 1(6), 250-266 (2009).
98. Put R, Vander Heyden Y. Review on modelling aspects in reversed-phase liquid chromatographic quantitative structure-retention relationships. Anal. Chim. Acta 602(2), 164-172 (2007). (Pubitemid 47539351)
99. Ghasemi J, Saaidpour S. QSRR prediction of the chromatographic retention behavior of painkiller drugs. J. Chromatogr. Sci. 47(2), 156-163 (2009).
100. Van Eenoo P, Delbeke FT. Metabolism and excretion of anabolic steroids in doping control-new steroids and new insights. J. Steroid Biochem. Mol. Biol. 101, 161-178 (2006). (Pubitemid 44573810)
101. Parr MK, Kazlauskas R, Schlorer N et al. 6a-methylandrostenedione: gas chromatographic mass spectrometric detection in doping control. Rapid Commun. Mass Spectrom 22, 321-329 (2008). (Pubitemid 351212857)
102. Teale P, Houghton E. Metabolism of anabolic steroids and their relevance to drug detection in horseracing. Bioanalysis 2(6), 1085-1107 (2010).
103. Kicman AT, Gower DB. Anabolic steroids in sport: biochemical, clinical and analytical perspectives. Ann. Clin. Biochem. 40, 321-356 (2003). (Pubitemid 36819551)
104. Ho EN, Kwok WH, Leung DK, Wan TS, Wong AS. Metabolic studies of turinabol in horses. Anal. Chim. Acta 586(1-2), 208-216 (2007). (Pubitemid 46240015)
105. Ho EN, Leung DK, Leung GN et al. Metabolic studies of mesterolone in horses. Anal. Chim. Acta 596(1), 149-155 (2007). (Pubitemid 47001908)
106. Wong JK, Tang FP, Wan TS. In vitro metabolic studies using homogenized horse liver in place of horse liver microsomes. Drug Test. Anal. 3(6), 393-399 (2011).
107. Leung GNW, Ho ENM, Leung DKK et al. Metabolic studies of clostebol acetate in horses. Chromatographia 61, 397-402 (2005). (Pubitemid 40569129)
108. Leung GN, Tang FP, Wan TS et al. In vitro and in vivo studies of androst-4-ene-3,6,17-trione in horses by gas chromatography-mass spectrometry. Biomed. Chromatogr. 24(7), 744-751 (2010).
109. Scarth JP, Spencer HA, Hudson SC, Teale P, Gray R P, Hillyer L. The application of in vitro technologies to study the metabolism of the androgenic/anabolic steroid stanozolol in the equine. Steroids 75, 57-69 (2010).
110. Taylor P, Scarth J P, Hillyer LL. Use of in vitro technologies to study Phase II conjugation in equine sports drug surveillance. Bioanalysis 2(12), 1971-1988 (2010).
111. Machnik M, Gerlach M, Kietzmann M et al. Detection and pharmacokinetics of tetrahydrogestrinone in horses. J. Vet. Pharmacol. Ther. 32(2), 197-202 (2009).
112. Lévesque JF, Gaudreault M, Houle R, Chauret N. Evaluation of human hepatocyte incubation as a new tool for metabolism study of androstenedione and norandrostenedione in a doping control perspective. J. Chromatogr. B 780(1), 145-153 (2002). (Pubitemid 35279753)
113. Lévesque JF, Gaudreault M, Aubin Y, Chauret N. Discovery, biosynthesis and structure elucidation of new metabolites of norandrostenedione using in vitro systems. Steroids 70(4), 305-317 (2005). (Pubitemid 40387385)
114. Kuuranne T, Pystynen KH, Thevis M, Leinonen A, Schänzer W, Kostiainen R. Screening of in vitro synthesized metabolites of 4,9,1 1-trien-3-one steroids by liquid chromatography mass spectrometry Eur. J. Mass Spectrom. 14(3), 181-189 (2008).
115. Lévesque JF, Templeton E, Trimble L, Berthelette C, 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(10), 3164-3172 (2005). (Pubitemid 40695472)
116. Gauthier J, Goudreault D, Poirer D, Ayotte C. Identifcation of drostanolone metabolites produced by cryopreserved human hepatocytes. Steroids 74 308-314 (2009).
117. Thevis M, Gerace E, Thomas A et al. Characterization of in vitro generated metabolites of the selective androgen receptor modulators S-22 and S-23 and in vivo comparison to post-administration canine urine specimens. Drug Test. Anal. 2(11-12), 589-598 (2010).
118. Lootens L, Meuleman P, Pozo OJ, Van Eenoo P, Leroux-Roels G, Delbeke FT. uPA+/+-SCID mouse with humanized liver as a model for in vivo metabolism of exogenous steroids: methandienone as a case study. Clin. Chem. 55(10), 1783-1793 (2009).
119. Lootens L, Meuleman P, Leroux-Roels G, Van Eenoo P. Metabolic studies with promagnon, methylclostebol and methasterone in the uPA(+/+)-SCID chimeric mice. J. Steroid Biochem. Mol. Biol. doi:10.1016/j.jsbmb.2011. 06.010 (2011) (Epub ahead of print).
120. Lootens L, Van Eenoo P, Meuleman P et al. Steroid metabolism in chimeric mice with humanized liver. Drug Test. Anal. 1(11-12), 531-537 (2009).
121. Pozo OJ, Lootens L, Van Eenoo P et al. Combination of liquid-chromatography tandem mass spectrometry in different scan modes with human and chimeric mouse urine for the study of steroid metabolism. Drug Test. Anal. 1(11-12), 554-567 (2009).
122. Botrè F. Humanized animal models to study drug metabolism: no longer a 'chimera'? Clin. Chem. 55(10), 1763-1764 (2009).
123. Beuck S, Möller I, Thomas A et al. Structure characterisation of urinary metabolites of the cannabimimetic JWH-018 using chemically synthesised reference material for the support of LC-MS/MS-based drug-testing. Anal. Bioanal. Chem. 401(2), 493-505 (2011).
124. Möller I, Wintermeyer A, Bender K et al. Screening for the synthetic cannabinoid JWH-018 and its major metabolites in human doping controls. Drug Test. Anal. 3(9), 609-620 (2011).
125. Brun EM, Hernández-Albors A, Ventura R, Puchades R, Maquieira A. Enzyme-linked immunosorbent assays for the synthetic steroid gestrinone. Talanta 82(4), 1581-1587 (2010).
126. Salvador JP, Sanchez-Baeza F, Marco MP. Preparation of antibodies for the designer steroid tetrahydrogestrinone and development of an enzyme-linked immunosorbent assay for human urine analysis. Anal. Chem. 79(10), 3734-3740 (2007). (Pubitemid 46799070)
127. Hungerford NL, Sortais B, Smart CG et al. Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17a-alkyl anabolic steroid metabolites. J. Steroid Biochem. Mol. Biol. 96, 317-334 (2005). (Pubitemid 41085837)
128. Fredolini C, Tamburro D, Gambara G et al. Nanoparticle technology: amplifying the effective sensitivity of biomarker detection to create a urine test for hGH. Drug Test. Anal. 1(9-10), 447-454 (2009).
129. Zierau O, Lehmann S, Vollmer G, Schänzer W, Diel P. Detection of anabolic steroid abuse using a yeast transactivation system. Steroids 73(11), 1143-1147(2008).
130. Wolf S, Diel P, Parr MK et al. Long-term detection of methyltestosterone (ab-) use by a yeast transactivation system. Arch. Toxicol. 85(4), 285-292 (2011).
131. Rijk JC, Ashwin H, van Kuijk SJ et al. Bioassay based screening of steroid derivatives in animal feed and SUPPL.ements. Anal. Chim. Acta 700(1-2), 183-188 (2011).
132. Rijk JC, Bovee TF, Groot MJ, Peijnenburg AA, Nielen MW. Evidence of the indirect hormonal activity of prohormones using liver S9 metabolic bioactivation and an androgen bioassay. Anal. Bioanal. Chem. 392(3), 417-425 (2008).
133. Rijk JC, Bovee TF, Wang S, Van Poucke C, Van Peteghem C, Nielen M W. Detection of anabolic steroids in dietary SUPPL.ements: the added value of an androgen yeast bioassay in parallel with a liquid chromato-graphy-tandem mass spectrometry screening method. Anal. Chim. Acta 637(1-2), 305-314 (2009).
134. Akram ON, Bursill C, Desai R et al. Evaluation of androgenic activity of nutraceutical-derived steroids using mammalian and yeast in vitro androgen bioassays. Anal. Chem. 83(6), 2065-2074 (2011).
135. Houtman CJ, Sterk SS, van de Heijning MP et al. Detection of anabolic androgenic steroid abuse in doping control using mammalian reporter gene bioassays. Anal. Chim. Acta 637(1-2), 247-258 (2009).
136. Bovee TF, Thevis M, Hamers AR, Peijnenburg AA, Nielen MW, Schoonen WG. SERMs and SARMs: detection of their activities with yeast based bioassays. J. Steroid Biochem. Mol. Biol. 118(1-2), 85-92 (2009).
137. Bovee TF, Lommerse JP, Peijnenburg AA, Fernandes EA, Nielen MW. A new highly androgen specifc yeast biosensor, enabling optimisation of (Q)SAR model approaches. J. Steroid Biochem. Mol. Biol. 108(1-2), 121-131 (2008). (Pubitemid 351173824)
138. Yuan X, Forman BM. Detection of designer steroids. Nucl. Recept. Signal. 3, e002 (2005).
139. Teale P, Barton C, Driver PM, Kay RG. Biomarkers: unrealized potential in sports doping analysis. Bioanalysis 1(6), 1103-1118 (2009).
140. Riedmaier I, Becker C, Pfaff W, Meyer HHD. The use of omic technologies for biomarker development to trace functions of anabolic agents. J. Chromatogr. A 1216(46), 8192-8199 (2009).
141. Dervilly-Pinel G, Weigel S, Lommen A et al. Assessment of two complementary liquid chromatography coupled to high-resolution mass spectrometry metabolomics strategies for the screening of anabolic steroid treatment in calves. Anal. Chim. Acta 700(1-2), 144-154 (2011).
142. Courant F, Pinel G, Bichon E, Monteau F, Antignac JP, Le Bizec B. Development of a metabolomic approach based on liquid chromatography-high- resolution mass spectrometry to screen for clenbuterol abuse in calves. Analyst 134(8), 1637-1646 (2009).
143. Bailly-Chouriberry L, Chu-Van E, Pinel G et al. Detection of secondary biomarker of met-eGH as a strategy to screen for somatotrophin misuse in horseracing. Analyst 133(2), 270-276 (2007). (Pubitemid 351172212)
144. Barton C, Beck P, Kay R, Teale P, Roberts J. Multiplexed LC-MS/MS analysis of horse plasma proteins to study doping in sport. Proteomics 9(11), 3058-3065 (2009).
145. Kieken F, Pinel G, Antignac JP et al. Development of a metabonomic approach based on LC-ESI-HRMS measurements for profling of metabolic changes induced by recombinant equine growth hormone in horse urine. Anal. Bioanal. Chem. 394(8), 2119-2128 (2009).
146. Bailly-Chouriberry L, Noguier F, Manchon L et al. Blood cells RNA biomarkers as a frst long-term detection strategy for EPO abuse in horseracing. Drug Test. Anal. 2(7), 339-345 (2010).
147. Holt RI. Detecting growth hormone abuse in athletes. Drug Test. Anal. 1(9-10), 426-433 (2009).
148. Barthel A, Bornstein SR, Benker G. Pilot study of serum inhibin B as a potential marker of testosterone doping in weight lifting men. Clin. J. Sport Med. 20(2), 117-119 (2010).
149. Varlet-Marie E, Audran M, Ashenden M, Sicart M-T, Piquemal D. Modifcation of gene expression: help to detect doping with erythropoiesis-stimulating agents. Am. J. Hematol. 84(11), 755-759 (2009).
150. Abellan R, Ventura R, Palmi I et al. Evaluation of immunoassays for the measurement of insulin and C-peptide as indirect biomarkers of insulin misuse in sport: values in selected population of athletes. J. Pharm. Biomed. Anal. 49(3), 793-799 (2009).
151. Van Renterghem P, Van Eenoo P, Sottas PE, Saugy M, Delbeke F. Subject-based steroid profling and the determination of novel biomarkers for DHT and DHEA misuse in sports. Drug Test. Anal. 2(11-12), 582-588 (2010).
152. Van Renterghem P, Van Eenoo P, Sottas PE, Saugy M, Delbeke F. A pilot study on subject-based comprehensive steroid profling: novel biomarkers to detect testosterone misuse in sports. Clin. Endocrinol. 75(1), 134-140 (2011).
153. Van Renterghem P, Van Eenoo P, DelbekeFT. Population based evaluation of a multi-parametric steroid profling on administered endogenous steroids in single low dose. Steroids 75(13-14), 1047-1057 (2010).
154. Van Renterghem P, Van Eenoo P, Geyer H, Schänzer W, Delbeke FT. Reference ranges for urinary concentrations and ratios of endogenous steroids, which can be used as markers for steroid misuse, in a Caucasian population of athletes. Steroids 75(2), 154-163 (2010).
155. Mareck U, Geyer H, Opfermann G, Thevis M, Schänzer W. Factors infuencing the steroid profle in doping control analysis. J. Mass Spectrom. 43(7), 877-891 (2008). (Pubitemid 352029656)
156. Mareck U, Geyer H, Fusshöller G et al. Reporting and managing elevated testosterone/epitestosterone ratios-novel aspects after fve years' experience. Drug Test. Anal. 2(11-12), 637-642 (2010).
157. Sottas PE, Robinson N, Rabin O, Saugy M. The athlete biological passport. Clin. Chem. 57(7), 969-976 (2011).
158. Sottas PE, Saugy M, Saudan C. Endogenous steroid profling in the athlete biological passport. Endocrinol. Metab. Clin. North Am. 39(1), 59-73 (2010).
159. Zorzoli M, Rossi F. Implementation of the biological passport: the experience of the International Cycling Union. Drug Test. Anal. 2(11-12), 542-547 (2010).
160. Wozny M. The biological passport and doping in athletics. Lancet 376(9735), 79 (2010).
161. Sottas PE, Robinson N, Saugy M. The athlete's biological passport and indirect markers of blood doping. In: Handbook of Experimental Pharmacology. Doping in Sports. Thieme D, Hemmersbach P (Eds). Springer, Heidelberg, Germany, 195, 305-326 (2010).
162. Henninge J, Pepaj M, Hullstein I, Hemmersbach P. Identifcation of CJC-1295, a growth-hormone-releasing peptide, in an unknown pharmaceutical preparation. Drug Test. Anal. 2(11-12), 647-650 (2010).
163. Guan F, Uboh CE, Soma LR, Rudy J. Sequence elucidation of an unknown cyclic peptide of high doping potential by ETD and CID tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 22(4), 718-730 (2011).
164. Thevis M, Geyer H, Mareck U, Schänzer W. Screening for synthetic steroids in human urine by LC-ESI-MS/MS. Rec. Adv. Doping Anal. (13), 147-155 (2005).
165. Nielen MWF, Bovee TFH. The potential of bioassays and time-of-fight mass spectrometry in urine testing for banned and designer steroids. Rec. Adv. Doping Anal. (13), 157-158 (2005).
166. Van Eenoo P, Spaerkeer A, Lootens L et al. Results of several (small) research projects at DoCoLab in 2005. Rec. Adv. Doping Anal. (14), 79-86 (2006).
167. Kuuranne T, Leinonen A, Thevis M, Schänzer W, Pystynen K-H, Kostiainen R. Metabolism of 'new' anabolic steroids: development of in vitro methodology in metabolite production and analytical techniques Rec. Adv. Doping Anal. (14), 161-168 (2006).
168. Schrader Y, Thevis M, Schänzer W. Quantitative determination of metabolic products of 19-norandrostenediol in human plasma using gas chromatography-mass spectrometry. Rec. Adv. Doping Anal. (14), 199-202 (2006).
169. Guddat S, Schänzer W, Wachsmuth P, Thevis M. Doping control screening procedure for Trenbolone analogues in human urine by LC-(APCI)-MS/MS. Rec. Adv. Doping Anal. (15), 397-400 (2007).
170. Kazlauskas R. WADA list. Rec. Adv. Doping Anal. (16), 21-32 (2008).
171. Van Eenoo P, Van Thuyne W, Pozo-Mendoza O et al. Results of several (small) research projects at DoCoLab in 2007. Rec. Adv. Doping Anal. (16), 33-40 (2008).
172. Thevis M, Kohler M, Schlörer N, Fußhöller G, Schänzer G. Screening for quinolinone-derived selective androgen receptor modulators using GC-MS and LC-MS/MS. Rec. Adv. Doping Anal. (16), 59-68 (2008).
173. Kazlauskas R, Agon V, Goebel C, Hine E, Trout GJ. ASDTL Projects 2008. Rec. Adv. Doping Anal. (17), 11-20 (2009).
174. Van Eenoo P, Deventer K, Pozo, Lootens L, Van Renterghem P, Delbeke FT. Results of several (small) research projects at DoCoLab in 2008. Rec. Adv. Doping Anal. (17), 29-34 (2009).
175. Parr MK, Haenelt N, Fußhöller G et al. Rec. Adv. Doping Anal. (17), 71-80 (2009).
176. Strano Rossi S, de la Torre X, Botrè F. A rapid method for the extraction and enantiomeric separation of amphetamine-type stimulants. Rec. Adv. Doping Anal. (17), 203-206 (2009).
177. Sobolevsky T, Prasolov I, Rodchenkov G. Designer stimulants recently identifed on black market. Rec. Adv. Doping Anal. 18, 245-248 (2010).