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) 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]