Clostebol
 | |
 | |
| Clinical data | |
|---|---|
| Other names | Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one |
| Drug class | Androgen; Anabolic steroid |
| ATC code |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.012.849 |
| Chemical and physical data | |
| Formula | C19H27ClO2 |
| Molar mass | 322.87 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (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.[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 reported to be 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] Chlorodehydromethyltestosterone (Oral Turinabol), combining the chemical structures of clostebol and metandienone, was widely used in the East German state-sponsored doping program.[3]
Medical uses
Clostebol acetate ointment has ophthalmological and dermatological use.[4]
Side effects
Chemistry
Clostebol, also known as 4-chlorotestosterone or as 4-chloroandrost-4-en-17β-ol-3-one, is a synthetic androstane steroid and a derivative of testosterone. It is specifically the 4-chlorinated derivative of testosterone.
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 U.S., 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 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.
- ^ "Doping for Gold: The State-Sponsored Doping Program". PBS. 2011-06-13.
- ^ Maccaroni E, Mele A, Del Rosso R, Malpezzi L (August 2011). "Clostebol acetate". Acta Crystallographica Section E. 67 (Pt 8): o1952-3. doi:10.1107/S1600536811026560. PMC 3212337. PMID 22090994.
- ^ a b Rahnema CD, Crosnoe LE, Kim ED (March 2015). "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology. 3 (2): 150–5. doi:10.1111/andr.307. PMID 25684733.
- ^ Breen, Matt (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension".
{{cite news}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN. 2016-04-29.
- ^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth - Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.
- ^ "Advokat: – Johaug fikk hele pakken". 2016-10-17.
- ^ "Slik hevder Johaug å ha fått i seg det forbudte stoffet". 2016-10-13.
- ^ "World's best cross-country skier Therese Johaug hit by new Norwegian doping scandal". October 13, 2016. Archived from the original on 2019-01-26. Retrieved 2016-10-18.