Clostebol
Anabolic steroid
Clostebol Other names Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one Drug class Androgen ; Anabolic steroid ATC code Legal status
(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 InfoCard 100.012.849 Formula C 19 H 27 Cl O 2 Molar mass 322.87 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
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Clostebol (INN Tooltip 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
Clostebol acetate ointment has ophthalmological and dermatological use.[5]
Side effects
Chemistry
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.[6]
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,[7] Dee Gordon of the Miami Marlins in 2016,[8] Olympic athlete Viktoria Orsi Toth in 2016,[9] Serie A soccer player José Luis Palomino of Club Atalanta , and Fernando Tatís Jr. of the San Diego Padres in 2022.[10] [11] 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.[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
^ 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 .
^ Index Nominum 2000: International Drug Directory . Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1 .
^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF) . World Anti-Doping Agency . Retrieved 2019-12-28 .
^ "Doping for Gold: The State-Sponsored Doping Program" . PBS. 2011-06-13.
^ Maccaroni E, Mele A, Del Rosso R, Malpezzi L (August 2011). "Clostebol acetate" . Acta Crystallographica Section E . 67 (Pt 8): o1952-3. Bibcode :2011AcCrE..67o1952M . doi :10.1107/S1600536811026560 . PMC 3212337 . PMID 22090994 .
^ 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 .
^ Breen M (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension" .
^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation" . ESPN. 2016-04-29.
^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth – Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03 .
^ Campanale S (2022-07-26). "Report Atalanta's Palomino Fails Doping Test" .
^ 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 .
^ "Padres' Tatis banned 80 games for PED violation" . 12 August 2022.
^ "Advokat: – Johaug fikk hele pakken" . 2016-10-17.
^ "Slik hevder Johaug å ha fått i seg det forbudte stoffet" . 2016-10-13.
^ "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 .
Androgens (incl. AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor antagonists Steroidogenesis inhibitors
Antigonadotropins
D2 receptor antagonists (prolactin releasers ) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
Estrogens (e.g., bifluranol , diethylstilbestrol , estradiol , estradiol esters , ethinylestradiol , ethinylestradiol sulfonate , paroxypropione )
GnRH agonists (e.g., leuprorelin )
GnRH antagonists (e.g., cetrorelix )
Progestogens (incl., chlormadinone acetate , cyproterone acetate , hydroxyprogesterone caproate , gestonorone caproate , medroxyprogesterone acetate , megestrol acetate )
Others
AR Tooltip Androgen receptor
Agonists SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A