From Wikipedia, the free encyclopedia
Anabolic steroid
Clostebol
Other names Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
Drug class
Androgen ;
Anabolic steroid
ATC code
Legal status
(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
PubChem
CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.012.849
Formula C 19 H 27 Cl O 2
Molar mass 322.87 g·mol−1 3D model (
JSmol )
O=C4C(\Cl)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
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
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Clostebol (
INN Tooltip 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]
Medical uses
Clostebol acetate ointment has ophthalmological and dermatological use.
[5]
Side effects
Chemistry
Clostebol, also known as 4-chlorotestosterone or as 4-chloroandrost-4-en-17β-ol-3-one, is a
synthetic
androstane
steroid and a
derivative of testosterone. It is specifically the 4-
chlorinated derivative of testosterone.
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.
[6]
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,
[7]
Dee Gordon of the
Miami Marlins in 2016,
[8] Olympic athlete
Viktoria Orsi Toth in 2016,
[9] Serie A soccer player
José Luis Palomino of Club
Atalanta , and
Fernando Tatís Jr. of the
San Diego Padres in 2022.
[10]
[11] Tatís Jr, who had missed the entirety of the season due to a broken wrist, accepted the suspension while claiming that it was an inadvertent breach after taking a
ringworm medication that he had failed to check the ingredients list for banned substances.
[12] and Orlando Galo from Club Sport Herediano in 2022
In 2016, urinalysis resulted in
Therese Johaug testing positive for clostebol.
[13]
[14]
[15]
Regulation
In the U.S., clostebol is listed as a
Schedule III controlled substance ,
[6] meaning the U.S. federal government considers it to have a potential for abuse as well as a currently accepted medical use.
See also
References
^
Anvisa (2023-03-31).
"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 2023-04-04).
Archived from the original on 2023-08-03. Retrieved 2023-08-15 .
^
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 2019-12-28 .
^
"Doping for Gold: The State-Sponsored Doping Program" . PBS. 2011-06-13.
^ Maccaroni E, Mele A, Del Rosso R, Malpezzi L (August 2011).
"Clostebol acetate" . Acta Crystallographica Section E . 67 (Pt 8): o1952-3.
Bibcode :
2011AcCrE..67o1952M .
doi :
10.1107/S1600536811026560 .
PMC
3212337 .
PMID
22090994 .
^
a
b Rahnema CD, Crosnoe LE, Kim ED (March 2015).
"Designer steroids – over-the-counter supplements and their androgenic component: review of an increasing problem" . Andrology . 3 (2): 150–155.
doi :
10.1111/andr.307 .
PMID
25684733 .
S2CID
6999218 .
^ Breen M (July 11, 2016).
"Phillies say they will welcome Stumpf back after drug suspension" .
^
"Marlins 2B Dee Gordon suspended 80 games after PEDs violation" . ESPN. 2016-04-29.
^
"Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth – Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03 .
^ Campanale S (2022-07-26).
"Report Atalanta's Palomino Fails Doping Test" .
^ Passan J (12 August 2022).
"San Diego Padres star Fernando Tatis Jr. suspended 80 games after testing positive for PED" .
ESPN.com . Retrieved 12 August 2022 .
^
"Padres' Tatis banned 80 games for PED violation" . 12 August 2022.
^
"Advokat: – Johaug fikk hele pakken" . 2016-10-17.
^
"Slik hevder Johaug å ha fått i seg det forbudte stoffet" . 2016-10-13.
^
"World's best cross-country skier Therese Johaug hit by new Norwegian doping scandal" . October 13, 2016. Archived from
the original on 2019-01-26. Retrieved 2016-10-18 .
Androgens (incl.
AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor
antagonists
Steroidogenesis inhibitors
Antigonadotropins
D2 receptor
antagonists (
prolactin releasers ) (e.g.,
domperidone ,
metoclopramide ,
risperidone ,
haloperidol ,
chlorpromazine ,
sulpiride )
Estrogens (e.g.,
bifluranol ,
diethylstilbestrol ,
estradiol ,
estradiol esters ,
ethinylestradiol ,
ethinylestradiol sulfonate ,
paroxypropione )
GnRH agonists (e.g.,
leuprorelin )
GnRH antagonists (e.g.,
cetrorelix )
Progestogens (incl.,
chlormadinone acetate ,
cyproterone acetate ,
hydroxyprogesterone caproate ,
gestonorone caproate ,
medroxyprogesterone acetate ,
megestrol acetate )
Others
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A