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Structure Database (LMSD)

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Common Name

4-Chlorotestosterone

Systematic Name

4-chloro-17β-hydroxyandrost-4-en-3-one

Synonyms

Clostebol

LM ID

LMST02020019

Formula

C₁₉H₂₇O₂Cl

Exact Mass

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322.169958

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Clostebol is an analytical reference standard that is categorized as an androgenic anabolic steroid. Clostebol is a chlorinated form of testosterone (ISO60154) that has been used as an athletic performance enhancer and to fatten cattle.^1,2,3 It is also detectible in urine. Formulations containing clostebol have been used to treat osteoporosis, anorexia, and certain types of liver disease.^4,5,6 Clostebol is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Calderón-Garcidueñas, L., Wen-Wang, L., Zhang, Y.J., et al. 8-Hydroxy-2'-deoxyguanosine, a major mutagenic oxidative DNA lesion, and DNA strand breaks in nasal respiratory epithelium of children exposed to urban pollution. Environ. Health Perspect. 107(6), 469-474 (1999).

2. Schanzer, 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(1-2), 23-48 (1993).

3. Lu, J., Fernández-Álvarez, M., Yang, S., et al. New clostebol metabolites in human urine by liquid chromatography time-of-flight tandem mass spectrometry and their application for doping control. J. Mass. Spectrom. 50(1), 191-197 (2015).

4. Debruyckere, G., de Sagher, R., and Van Peteghem, C. Clostebol-positive urine after consumption of contaminated meat. Clin. Chem. 38(9), 1869-1873 (1992).

5. Pereira, H.M., Marques, M.A., Talhas, I.B., et al. Incidental clostebol contamination in athletes after sexual intercourse. Clin. Chem. 50(2), 456-457 (2004).

6. Crabbe, P., Van Peteghem, C., Salden, M., et al. Influence of the hapten conjugation site on the characteristics of antibodies generated against metabolites of clostebol acetate. J. Agric. Food Chem. 48(8), 3633-3638 (2000).