Clostebol

Clostebol
Clinical data
Other names	Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
Drug class	Androgen; Anabolic steroid
ATC code	None;
Legal status
Legal status	BR: Class C5 (Anabolic steroids); 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 ;
PubChem CID	68947;
DrugBank	DB01521 ;
ChemSpider	62171 ;
UNII	Z7D4G976SH;
KEGG	D07731 ;
ChEMBL	ChEMBL2106571 ;
CompTox Dashboard (EPA)	DTXSID5046192 ;
ECHA InfoCard	100.012.849
Chemical and physical data
Formula	C19H27ClO2
Molar mass	322.87 g·mol−1
3D model (JSmol)	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 ; Key:KCZCIYZKSLLNNH-FBPKJDBXSA-N ;
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Clostebol (INNTooltip International Nonproprietary Name; also known as 4-chlorotestosterone) 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.

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