Clostebol

Clostebol
Clinical data

Trade names	Trofodermin-S
ATC code	none
Legal status
Legal status	CA: Schedule IV
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	1093-58-9^Y
PubChem (CID)	68947
DrugBank	DB01521^Y
ChemSpider	62171^Y
UNII	Z7D4G976SH^Y
KEGG	D07731^Y
ChEMBL	CHEMBL2106571^N
ECHA InfoCard	100.012.849
Chemical and physical data
Formula	C₁₉H₂₇ClO₂
Molar mass	322.869 g/mol
3D model (Jmol)	Interactive image
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?)

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 marketed, under the brand name Trofodermin-S in Mexico.

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

Clostebol acetate ointment has ophthalmological and dermatological use.

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.

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,Dee Gordon of the Miami Marlins in 2016, and Olympic athlete Viktoria Orsi Toth in 2016.

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Wikipedia