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 ;
	(what is this?) (verify)

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.^[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]

^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1.
^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 28 December 2019.
^ "Doping for Gold: The State-Sponsored Doping Program". PBS. 13 June 2011.

[1] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1.

[WADA-3] "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 28 December 2019.

[4] "Doping for Gold: The State-Sponsored Doping Program". PBS. 13 June 2011.

[1]

[2]

[3]

[4]