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Other names | Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one |
Drug class | Androgen; Anabolic steroid |
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ECHA InfoCard | 100.012.849 |
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Formula | C19H27ClO2 |
Molar mass | 322.87 g·mol−1 |
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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.[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]
Clostebol acetate ointment has ophthalmological and dermatological use.[5]
See also: Anabolic steroid § Adverse effects |
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.
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]
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]
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.