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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
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

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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 (infected) skin wounds such as abrasions, erosions, fissures, burns and to help speed up the healing of the area.

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]

In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[15][16][17]

Italian tennis player Jannik Sinner tested positive for clostebol in two different urine samples on 8 March and 10 March 2024.[18] 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.[19] 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.[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". Archived from the original on 17 August 2016.
  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. ^ "Advokat: – Johaug fikk hele pakken" [Lawyer: - Johaug got the whole package]. NRK (in Norwegian). 17 October 2016.
  16. ^ 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).
  17. ^ 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.
  18. ^ 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.
  19. ^ 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.
  20. ^ "Decision of independent tribunal: International Tennis Integrity Agency (ITIA) vs. Jannik Sinner (SR/250/2024)" (PDF). Sport Resolutions. 19 August 2024.
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