Clostebol

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Clostebol
Clostebol.svg
Clostebol molecule ball.png
Clinical data
Synonyms Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
Drug class Androgen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.012.849 Edit this at Wikidata
Chemical and physical data
Formula C19H27ClO2
Molar mass 322.869 g/mol
3D model (JSmol)
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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 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[edit]

Clostebol acetate ointment has ophthalmological and dermatological use.[4]

Side effects[edit]

Chemistry[edit]

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[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 U.S., clostebol is listed as a Schedule III substance.[5]

See also[edit]

References[edit]

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1. 
  2. ^ "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Archived from the original (PDF) on 2012-05-13. Retrieved 2012-05-10. 
  3. ^ "Doping for Gold: The State-Sponsored Doping Program". PBS. 
  4. ^ MacCaroni, E; Mele, A; Del Rosso, R; Malpezzi, L (2011). "Clostebol acetate". Acta Crystallographica Section E Structure Reports Online. 67 (Pt 8): o1952–o1953. doi:10.1107/S1600536811026560. PMC 3212337Freely accessible. PMID 22090994. 
  5. ^ a b "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology. 3 (2): 150–155. doi:10.1111/andr.307. 
  6. ^ Matt Breen (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension". 
  7. ^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN. 
  8. ^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth - Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03. 
  9. ^ https://www.nrk.no/sport/advokat_-_-johaug-fikk-hele-pakken-1.13182815
  10. ^ http://www.dagbladet.no/sport/slik-hevder-johaug-a-ha-fatt-i-seg-det-forbudte-stoffet/63962006
  11. ^ http://nordic.businessinsider.com/therese-johaug-tested-positive-for-doping----norwegian-ski-federation-cancels-huge-kick-off-2016-10/