Clostebol
 | |
| Clinical data | |
|---|---|
| Trade names | Trofodermin-S |
| ATC code | none |
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| 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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| (what is this?) (verify) | |
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. 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]
Non-doping uses
Clostebol acetate ointment has ophthalmological and dermatological use.[4]
Society and culture
Nutritional supplements
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
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
In the US, clostebol is listed as a Schedule III substance.[5]
See also
References
- ↑ 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/
- 1 2 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/