Clostebol

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. 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
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
IUPAC name
  • (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
Chemical and physical data
FormulaC19H27ClO2
Molar mass322.87 g·mol−1
3D model (JSmol)
SMILES
  • O=C4C(\Cl)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
InChI
  • 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 Y
  • Key:KCZCIYZKSLLNNH-FBPKJDBXSA-N Y
 NY (what is this?)  (verify)

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

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

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 synthetic androstane steroid and 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.[5]

Publicized abuse cases

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] Olympic athlete Viktoria Orsi Toth in 2016,[8] Serie A soccer player José Luis Palomino of Club Atalanta, and Fernando Tatís Jr. of the San Diego Padres in 2022.[9][10] 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.[11] and Orlando Galo from Club Sport Herediano in 2022

In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[12][13][14]

Regulation

In the U.S., clostebol is listed as a Schedule III controlled substance,[5] 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. 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 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.
  3. "Doping for Gold: The State-Sponsored Doping Program". PBS. 2011-06-13.
  4. Maccaroni E, Mele A, Del Rosso R, Malpezzi L (August 2011). "Clostebol acetate". Acta Crystallographica Section E. 67 (Pt 8): o1952-3. doi:10.1107/S1600536811026560. PMC 3212337. PMID 22090994.
  5. 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.
  6. Breen M (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. 2016-04-29.
  8. "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth – Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.
  9. Campanale, Susy (2022-07-26). "Report Atalanta's Palomino Fails Doping Test".{{cite web}}: CS1 maint: url-status (link)
  10. Passan, Jeff (12 August 2022). "San Diego Padres star Fernando Tatis Jr. suspended 80 games after testing positive for PED". ESPN.com. Retrieved 12 August 2022.
  11. "Padres' Tatis banned 80 games for PED violation". 12 August 2022.
  12. "Advokat: – Johaug fikk hele pakken". 2016-10-17.
  13. "Slik hevder Johaug å ha fått i seg det forbudte stoffet". 2016-10-13.
  14. "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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