Clostebol

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Clostebol
Clinical data
Other namesChlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Identifiers
  • (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
JSmol)
  • O=C4C(\Cl)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
  • InChI=1S/C19H27ClO2/c1-18-10-8-15(21)17(20)14(18)4-3-11-12-5-6-16(22)19(12,2)9-7-13(11)18/h11-13,16,22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1 checkY
  • Key:KCZCIYZKSLLNNH-FBPKJDBXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Clostebol (

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.[2]

Clostebol is a weak AAS with potential use as a

performance enhancing drug. It is currently banned by the World Anti-Doping Agency.[3] Chlorodehydromethyltestosterone (Oral Turinabol), combining the chemical structures of clostebol and metandienone, was widely used in the East German state-sponsored doping program.[4]

Medical uses

Clostebol acetate ointment has ophthalmological and dermatological use.[5]

Side effects

See also: Anabolic steroid § Adverse effects

Chemistry

See also:
List of androgens/anabolic steroids

Clostebol, also known as 4-chlorotestosterone or as 4-chloroandrost-4-en-17β-ol-3-one, is 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.[6]

Publicized abuse cases

Use of clostebol has led to the suspension of a number of athletes in various sports including

ringworm medication that he had failed to check the ingredients list for banned substances.[12]
and Orlando Galo from Club Sport Herediano in 2022

In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[13][14][15]

Regulation

In the U.S., clostebol is listed as a Schedule III controlled substance,[6] meaning the U.S. federal government considers it to have a potential for abuse as well as a currently accepted medical use.

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ISBN 978-3-88763-075-1
    .
  3. ^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.
  4. ^ "Doping for Gold: The State-Sponsored Doping Program". PBS. 2011-06-13.
  5. PMID 22090994
    .
  6. ^
    S2CID 6999218
    .
  7. ^ Breen M (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension".
  8. ^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN. 2016-04-29.
  9. ^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth – Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.
  10. ^ Campanale S (2022-07-26). "Report Atalanta's Palomino Fails Doping Test".
  11. ^ Passan J (12 August 2022). "San Diego Padres star Fernando Tatis Jr. suspended 80 games after testing positive for PED". ESPN.com. Retrieved 12 August 2022.
  12. ^ "Padres' Tatis banned 80 games for PED violation". 12 August 2022.
  13. ^ "Advokat: – Johaug fikk hele pakken". 2016-10-17.
  14. ^ "Slik hevder Johaug å ha fått i seg det forbudte stoffet". 2016-10-13.
  15. ^ "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.
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