Clostebol
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| Clinical data | |
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| Trade names | Trofodermin-S |
| ATC code | none |
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Systematic (IUPAC) name: (8S,9S,10R,13S,14S,17S)-4-Chloro-17-hydroxy-10,13-dimethyl- 1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
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| CAS Number | 1093-58-9  |
| PubChem (CID) | 68947 |
| DrugBank | DB01521 |
| ChemSpider | 62171 |
| UNII | Z7D4G976SH |
| KEGG | D07731 |
| ChEMBL | CHEMBL2106571  |
| Chemical and physical data | |
| Formula | C19H27ClO2 |
| Molar mass | 322.869 g/mol |
| 3D model (Jmol) | Interactive image |
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Clostebol (INN), also known as 4-chlorotestosterone, usually as the ester clostebol acetate, is a synthetic anabolic androgenic steroid (AAS). Clostebol is the 4-chloro derivative of the natural hormone testosterone. The chlorination prevents conversion to dihydrotestosterone (DHT) while also rendering the chemical incapable of conversion to estrogen.[citation needed] Although usually used as an ester including clostebol acetate (Macrobin, Steranabol, Alfa-Trofodermin, Megagrisevit), clostebol caproate (Macrobin-Depot), or clostebol propionate (Yonchlon), unmodified/non-esterified clostebol is also marketed, under the brand name Trofodermin-S in Mexico.[1]
Clostebol is a weak AAS with potential use as a performance enhancing drug. It is currently banned by the World Anti-Doping Agency.[2] Oral Turinabol, combining the chemical structures of clostebol and dianabol, was widely used in the East German state-sponsored doping program.[3]
Contents
Non-doping uses[edit]
Clostebol acetate ointment has ophthalmological and dermatological use.[4]
Society and culture[edit]
Nutritional supplements[edit]
A related anabolic steroid, methylclostebol, is a common additive in so-called dietary supplements, generally listed in the convoluted form 4-chloro-17α-methyl-androst-4-en-17β-ol-3-one.[5]
Publicized abuse cases[edit]
Use of clostebol has led to the suspension of a number of athletes in various sports including Freddy Galvis of the Philadelphia Phillies in 2012,[6] Dee Gordon of the Miami Marlins in 2016,[7] and Olympic athlete Viktoria Orsi Toth in 2016.[8]
In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[9][10][11]
Regulation[edit]
In the US, clostebol is listed as a Schedule III substance.[5]
See also[edit]
References[edit]
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1.
- ^ "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-05-10.
- ^ "Doping for Gold: The State-Sponsored Doping Program". PBS.
- ^ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3212337/
- ^ a b http://onlinelibrary.wiley.com/doi/10.1111/andr.307/full
- ^ Matt Breen (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension".
- ^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN.
- ^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth - Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.
- ^ https://www.nrk.no/sport/advokat_-_-johaug-fikk-hele-pakken-1.13182815
- ^ http://www.dagbladet.no/sport/slik-hevder-johaug-a-ha-fatt-i-seg-det-forbudte-stoffet/63962006
- ^ http://nordic.businessinsider.com/therese-johaug-tested-positive-for-doping----norwegian-ski-federation-cancels-huge-kick-off-2016-10/
