Clostebol

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Clostebol
Clostebol.svg
Clostebol molecule ball.png
Clinical data
SynonymsChlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.012.849 Edit this at Wikidata
Chemical and physical data
FormulaC19H27ClO2
Molar mass322.869 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. 67 (Pt 8): o1952–o1953. doi:10.1107/S1600536811026560. PMC 3212337. 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/