Clostebol

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Clostebol
Clostebol.svg
Clinical data
Trade names Trofodermin-S
ATC code
  • none
Legal status
Legal status
Identifiers
Synonyms Chlorotestosterone; 4-Chlorotestosterone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.012.849
Chemical and physical data
Formula C19H27ClO2
Molar mass 322.869 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

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.[1]

Clostebol is a weak AAS with potential use as a performance enhancing drug. It is currently banned by the World Anti-Doping Agency.[2] Oral Turinabol, combining the chemical structures of clostebol and metandienone, was widely used in the East German state-sponsored doping program.[3]

Medical uses[edit]

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

Side effects[edit]

Chemistry[edit]

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[edit]

Nutritional supplements[edit]

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[edit]

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] and Olympic athlete Viktoria Orsi Toth in 2016.[8]

In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[9][10][11]

Regulation[edit]

In the U.S., clostebol is listed as a Schedule III substance.[5]

See also[edit]

References[edit]