Metabolism of stanozolol: Chemical synthesis and identification of a major canine urinary metabolite by liquid chromatography-electrospray ionisation ion trap mass spectrometry

Journal of Steroid Biochemistry and Molecular Biology

Volumn 117, Issue 4-5, 2009, Pages 152-158

  Stewart, Rhiannon T ^a   McKinney, Andrew R ^b   Kerwick, Carmel M ^c   Young, E Bruce ^c   Vadasz, Andrew ^b   Cade, Ian A ^a   Willis, Anthony C ^a   McLeod, Malcolm D ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b Australian Racing Forensic Laboratory   (Australia)

^c DEPARTMENT OF EMPLOYMENT ECONOMIC DEVELOPMENT AND INNOVATION   (Australia)

Author keywords

6 Hydroxystanozolol; Anabolic androgenic steroid; Canine metabolism; Electrospray ionisation mass spectrometry; Liquid chromatography; Stanozolol

Indexed keywords

6 ALPHA HYDROXYSTANOZOLOL; 6 BETA HYDROXYSTANOZOLOL; DRUG METABOLITE; GLUCURONIDE; STANABOLIC; STANOZOLOL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DOG; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; HORMONE METABOLISM; ION TRAP MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; MALE; METABOLITE; NONHUMAN; PROTEIN HYDROLYSIS; SOLID PHASE EXTRACTION; STEROID HYDROXYLATION; STEROID URINE LEVEL; URINALYSIS; URINARY EXCRETION;

ANABOLIC AGENTS; ANDROGENS; ANIMALS; CHROMATOGRAPHY, LIQUID; CRYSTALLOGRAPHY, X-RAY; DOGS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, MOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STANOZOLOL;

EID: 70350334761     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2009.09.002     Document Type: Article

References (25)

1. Schänzer W. Metabolism of anabolic androgenic steroids. Clin. Chem. 42 (1996) 1001-1020
2. 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
3. Houghton E., Dumasia M.C., and Teale P. Some applications of chromatography to steroid analysis in the horse. Analyst 113 (1988) 1179-1187
4. Biddle S.T.B., O'Donnell A., Houghton E., and Creaser C. Metabolism of methyltestosterone in the greyhound. Rapid Commun. Mass Spectrom. 23 (2009) 713-721
5. Williams T.M., Kind A.J., and Hill D.W. In vitro biotransformation of anabolic steroids in canines. J. Vet. Pharmacol. Therap. 23 (2000) 57-66
6. Williams T.M., Kind A.J., Hyde W.G., and Hill D.W. Characterization of urinary metabolites of testosterone, methyltestosterone, mibolerone and boldenone in greyhound dogs. J. Vet. Pharmacol. Therap. 23 (2000) 121-129
7. Williams K.R., Anderson R.A., and Grey P.J. Metabolism of anabolic agents in the racing greyhound. Anal. Chim. Acta 275 (1993) 163-172
8. Brockwell M., Knox J., Stenhouse A., and Ralston J. The identification of the metabolites of testosterone 19-nortestosterone and 1-dehydrotestosteone in greyhound urine. In: Short C.R. (Ed). Proc. 9th Int. Conf. Racing Analysts and Veterinarians (1992), R&W Publications, Newmarket, UK 57-68
9. MacDougall D.F., and Jondorf W.R. 19-nortestosterone detection in canine plasma after intramuscular administration of 19-nortestosterone phenylpropionate. Res. Vet. Sci. 47 (1989) 399-401
10. Poelmans S., De Wasch K., De Brabander H.F., Van De Wiele M., Courtheyn D., van Ginkel L.A., Sterk S.S., Delahaut Ph., Dubois M., Schilt R., Nielen M., Vercammen J., Impens S., Stephany R., Hamoir T., Pottie G., Van Poucke C., and Van Peteghem C. Analytical possibilities for the detection of stanozolol and its metabolites. Anal. Chim. Acta 473 (2002) 39-47
11. A preliminary account of this research has been presented at the 17th International Conference of Racing Analysts and Veterinarians: A.R. McKinney, R.T. Stewart, C.M. Kerwick, E.B. Young, A.Vadasz, M.D. McLeod, The metabolism of synthetic anabolic-androgenic steroids in the greyhound: boldenone undecylenate and stanozolol, Proc. 17th Int. Conf. Racing Analysts and Veterinarians, R&W Publications, Newmarket, UK, in press.
12. Tang P.W., and Crone D.L. A new method for hydrolyzing sulfate and glucuronyl conjugates of steroids. Anal. Biochem. 182 (1989) 289-294
13. 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
14. Schänzer W., Opfermann G., and Donike M. Metabolism of stanozolol: identification and synthesis of urinary metabolites. J. Steroid Biochem. 36 (1990) 153-174
15. Mück W.M., and Henion J.D. High-performance liquid chromatography/tandem mass spectrometry: its use for the identification of stanozolol and its major metabolites in human and equine urine. Biomed. Environ. Mass Spectrom. 19 (1990) 37-51
16. Ferchaud V., Le Bizec B., Montrade M.-P., Maume D., Monteau F., and André F. Gas chromatographic-mass spectrometric identification of main metabolites of stanozolol in cattle after oral and subcutaneous administration. J. Chromatogr. B 695 (1997) 269-277
17. Nielen M.W.F., van Engelen M.C., Zuiderent R., and 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 586 (2007) 122-129
18. Thevis M., Makarov A.A., Horning S., and Schänzer W. Mass spectrometry of stanozolol and its analogues using electrospray ionization and collision-induced dissociation with quadrupole-linear ion trap and linear ion trap-orbitrap hybrid mass analyzers. Rapid Commun. Mass Spectrom. 19 (2005) 3369-3378
19. McKinney A.R., Suann C.J., Dunstan A.J., Mulley S.L., Ridley D.D., and Stenhouse A.M. Detection of stanozolol and its metabolites in equine urine by liquid chromatography-electrospray ionization ion trap mass spectrometry. J. Chromatogr. B 811 (2004) 75-83
20. +-ATPase inhibitors derived from a 5α,14α-androstane scaffold as positive inotropic compounds. J. Med. Chem. 46 (2003) 3644-3654
21. Crystallographic data (excluding structure factors) for the structure of compounds 5 and 3 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 738446 (5) and CCDC 738445 (3). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
22. Filler R. Oxidations and dehydrogenations with N-bromosuccinimide and related N-haloimides. Chem. Rev. 63 (1963) 21-43
23. 14C] stanozolol. J. Labelled Compd. Radiopharm. 20 (1983) 1227-1228
24. 13C NMR of pyrazoles. Magn. Reson. Chem. 31 (1993) 107-168
25. Corey E.J., and Schmidt G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in approtic media. Tetrahedron Lett. 20 (1979) 399-402