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 ;
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	322.869 g/mol 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 (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 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 dianabol, was widely used in the East German state-sponsored doping program.^[3]

Non-doping uses

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

Society and culture

Nutritional supplements

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

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

In the US, clostebol is listed as a Schedule III substance.^[5]

References

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1.
^ "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-05-10.
^ "Doping for Gold: The State-Sponsored Doping Program". PBS.
^ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3212337/
^ ^a ^b http://onlinelibrary.wiley.com/doi/10.1111/andr.307/full
^ Matt Breen (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension".
^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN.
^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth - Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.
^ https://www.nrk.no/sport/advokat_-_-johaug-fikk-hele-pakken-1.13182815
^ http://www.dagbladet.no/sport/slik-hevder-johaug-a-ha-fatt-i-seg-det-forbudte-stoffet/63962006
^ http://nordic.businessinsider.com/therese-johaug-tested-positive-for-doping----norwegian-ski-federation-cancels-huge-kick-off-2016-10/

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

[2] "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-05-10.

[3] "Doping for Gold: The State-Sponsored Doping Program". PBS.

[4] ttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC3212337/

[Designer_steroids-5] ttp://onlinelibrary.wiley.com/doi/10.1111/andr.307/full

[6] Matt Breen (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension".

[7] "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN.

[8] "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth - Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.

[9] ttps://www.nrk.no/sport/advokat_-_-johaug-fikk-hele-pakken-1.13182815

[10] ttp://www.dagbladet.no/sport/slik-hevder-johaug-a-ha-fatt-i-seg-det-forbudte-stoffet/63962006

[11] ttp://nordic.businessinsider.com/therese-johaug-tested-positive-for-doping----norwegian-ski-federation-cancels-huge-kick-off-2016-10/

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