Clostebol

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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.012.849 Edit this at Wikidata
Chemical and physical data
FormulaC19H27ClO2
Molar mass322.87 g·mol−1
3D model (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 (INNTooltip International Nonproprietary Name; 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.[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

[edit]

Clostebol acetate ointment has ophthalmological and dermatological use.[5] In some countries, such as Italy, it is available without a prescription as a topical cream or spray for the treatment of skin wounds such as abrasions, erosions, fissures and burns. In Italy, it is sold as a spray and cream, with the brand name Trofodermin, containing a combination of clostebol acetate and neomycin.[6]

Side effects

[edit]
See also: Anabolic steroid § Adverse effects

Chemistry

[edit]
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 synthetic androstane steroid and a derivative of testosterone. It is specifically the 4-chlorinated derivative of testosterone.

Society and culture

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Nutritional supplements

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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.[7]

Publicized abuse or contamination cases

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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,[8] Dee Gordon of the Miami Marlins in 2016,[9] Olympic athlete Viktoria Orsi Toth in 2016,[10] Serie A soccer player José Luis Palomino of Club Atalanta[11], Orlando Galo from C.S. Herediano in 2022,[12] and Fernando Tatís Jr. of the San Diego Padres in 2022.[13] Tatís Jr, who had missed the entirety of the season due to a broken wrist, accepted the suspension while claiming that it was an inadvertent breach after taking a ringworm medication that he had failed to check the ingredients list for banned substances.[14]

Italian tennis player Jannik Sinner tested positive for clostebol in two different urine samples on 8 March and 10 March 2024.[15] The International Tennis Integrity Agency (ITIA) found Sinner was inadvertently contaminated with the substance by his physiotherapist who had been applying a healing spray, available over-the counter in Italy, to treat a cut on his own hand and had then carried out treatments on Sinner.[16] Sinner was stripped of $325,000 in prize money and 400 ranking points earned at the Indian Wells Open, but wasn't suspended because an independent tribunal ruled that it was not intentional.[15][16][17]

In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[18][19][20]

Regulation

[edit]

In the U.S., clostebol is listed as a Schedule III controlled substance,[7] meaning the U.S. federal government considers it to have a potential for abuse as well as a currently accepted medical use.

See also

[edit]

References

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  1. ^ Anvisa (31 March 2023). "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 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1.
  3. ^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 28 December 2019.
  4. ^ "Doping for Gold: The State-Sponsored Doping Program". PBS. 13 June 2011.
  5. ^ Maccaroni E, Mele A, Del Rosso R, Malpezzi L (August 2011). "Clostebol acetate". Acta Crystallographica Section E: Structure Reports Online. 67 (Pt 8): o1952–o1953. Bibcode:2011AcCrE..67o1952M. doi:10.1107/S1600536811026560. PMC 3212337. PMID 22090994.
  6. ^ de la Torre X, Colamonici C, Iannone M, Jardines D, Molaioni F, Botrè F (November 2020). "Detection of clostebol in sports: Accidental doping?". Drug Testing and Analysis. 12 (11–12): 1561–1569. doi:10.1002/dta.2951. PMID 33119965.
  7. ^ 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): 150–155. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.
  8. ^ Breen M (11 July 2016). "Phillies say they will welcome Stumpf back after drug suspension".
  9. ^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN. 29 April 2016.
  10. ^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth" [Rio 2016, beach volleyball: confirmation of doping for Viktoria Orsi Toth]. Panorama (in Italian). 3 August 2016. Retrieved 3 August 2016.
  11. ^ Campanale S (26 July 2022). "Report Atalanta's Palomino Fails Doping Test".
  12. ^ "World Cup doping: Costa Rica's Galo positive for steroid". AP. 22 October 2022.
  13. ^ 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.
  14. ^ Passan J (12 August 2022). "Padres' Tatis banned 80 games for PED violation". ESPN.
  15. ^ a b "Jannik Sinner, world No. 1, tested positive for a steroid twice but will not be suspended". Tennis.com. Associated Press. 20 August 2024. Retrieved 20 August 2024.
  16. ^ a b "Jannik Sinner cleared of any wrongdoing after twice testing positive for banned substance in March". BBC Sport. 20 August 2024. Retrieved 21 August 2024.
  17. ^ "Decision of independent tribunal: International Tennis Integrity Agency (ITIA) vs. Jannik Sinner (SR/250/2024)" (PDF). Sport Resolutions. 19 August 2024.
  18. ^ "Advokat: – Johaug fikk hele pakken" [Lawyer: - Johaug got the whole package]. NRK (in Norwegian). 17 October 2016.
  19. ^ Tingve PM, Skaug TR (13 October 2016). "Slik hevder Johaug å ha fått i seg det forbudte stoffet" [This is how Johaug claims to have ingested the prohibited substance]. Dagbladet (in Norwegian).
  20. ^ Carlström V (13 October 2016). "World's best cross-country skier Therese Johaug hit by new Norwegian doping scandal". Insider Inc. Bonnier Business Media Sweden AB. Archived from the original on 26 January 2019. Retrieved 18 October 2016.
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