clostebol
{{Short description|Anabolic steroid}}
{{Use dmy dates|date=January 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443539149
| 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
| image = Clostebol.svg
| image_class = skin-invert-image
| width = 225px
| image2 = Clostebol molecule ball.png
| width2 = 225px
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_BR = C5
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}
| legal_CA = Schedule IV
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| class = Androgen; Anabolic steroid
| bioavailability =
| protein_bound =
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| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1093-58-9
| ATC_prefix = None
| ATC_suffix =
| PubChem = 68947
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2106571
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01521
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62171
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z7D4G976SH
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07731
| synonyms = Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
| C=19 | H=27 | Cl=1 | O=2
| SMILES = O=C4C(\Cl)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KCZCIYZKSLLNNH-FBPKJDBXSA-N
}}
Clostebol ({{abbrlink|INN|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.{{Citation needed|date=July 2016}} 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.{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA265|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=265–}}
Clostebol is a weak AAS with potential use as a performance enhancing drug. It is currently banned by the World Anti-Doping Agency.{{cite web|url=https://www.wada-ama.org/sites/default/files/wada_2020_english_prohibited_list_0.pdf|title=The World Anti-Doping Code: The 2020 Prohibited List|publisher=World Anti-Doping Agency|access-date=2019-12-28}} Chlorodehydromethyltestosterone (Oral Turinabol), combining the chemical structures of clostebol and metandienone, was widely used in the East German state-sponsored doping program.{{Cite web | url = https://www.pbs.org/wnet/secrets/the-state-sponsored-doping-program/52/ | title = Doping for Gold: The State-Sponsored Doping Program | publisher = PBS| date = 2011-06-13 }}
Medical uses
Clostebol acetate ointment has ophthalmological and dermatological use.{{cite journal | vauthors = Maccaroni E, Mele A, Del Rosso R, Malpezzi L | title = Clostebol acetate | journal = Acta Crystallographica Section E: Structure Reports Online | volume = 67 | issue = Pt 8 | pages = o1952–o1953 | date = August 2011 | pmid = 22090994 | pmc = 3212337 | doi = 10.1107/S1600536811026560 | bibcode = 2011AcCrE..67o1952M }} In some countries, such as Italy, it is available without a prescription as a topical cream or spray for the treatment of (infected) skin wounds such as abrasions, erosions, fissures, burns and to help speed up the healing of the area.
In Italy, it is sold as a spray and cream, with the brand name Trofodermin, containing a combination of clostebol acetate and neomycin.{{cite journal | vauthors = de la Torre X, Colamonici C, Iannone M, Jardines D, Molaioni F, Botrè F | title = Detection of clostebol in sports: Accidental doping? | journal = Drug Testing and Analysis | volume = 12 | issue = 11–12 | pages = 1561–1569 | date = November 2020 | pmid = 33119965 | doi = 10.1002/dta.2951 }}
Side effects
{{See also|Anabolic steroid#Adverse effects}}
Chemistry
{{See also|List of androgens/anabolic steroids}}
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.{{cite journal | vauthors = Rahnema CD, Crosnoe LE, Kim ED | title = Designer steroids – over-the-counter supplements and their androgenic component: review of an increasing problem | journal = Andrology | volume = 3 | issue = 2 | pages = 150–155 | date = March 2015 | pmid = 25684733 | doi = 10.1111/andr.307 | s2cid = 6999218 | doi-access = free }}
=Publicized abuse or contamination 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,{{cite news | title = Phillies say they will welcome Stumpf back after drug suspension | vauthors = Breen M | date = July 11, 2016 | url = http://articles.philly.com/2016-07-11/sports/74372443_1_freddy-galvis-carlos-ruiz-antonio-bastardo | archive-url = https://web.archive.org/web/20160817013747/http://articles.philly.com/2016-07-11/sports/74372443_1_freddy-galvis-carlos-ruiz-antonio-bastardo | url-status = dead | archive-date = 17 August 2016 }} Dee Gordon of the Miami Marlins in 2016,{{cite web | url = https://www.espn.com/mlb/story/_/id/15425125/dee-gordon-miami-marlins-banned-80-games-peds-violation | title = Marlins 2B Dee Gordon suspended 80 games after PEDs violation | publisher = ESPN| date = 2016-04-29 }} Olympic athlete Viktoria Orsi Toth in 2016,{{Cite web|url=http://www.panorama.it/sport/altri-sport/rio-2016-beach-volley-viktoria-orsi-toth-doping/|title=Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth | trans-title = Rio 2016, beach volleyball: confirmation of doping for Viktoria Orsi Toth | work = Panorama|date=2016-08-03|language=it-IT|access-date=2016-08-03}} Serie A soccer player José Luis Palomino of Club Atalanta,{{cite web | vauthors = Campanale S |date=2022-07-26 |title=Report Atalanta's Palomino Fails Doping Test |url=https://football-italia.net/report-atalantas-palomino-fails-doping-test/ }} Orlando Galo from C.S. Herediano in 2022,{{Cite web|url=https://apnews.com/article/world-cup-soccer-sports-middle-east-doping-0b95466619563d24bc785d8b5be13f9c|title=World Cup doping: Costa Rica’s Galo positive for steroid | work = AP|date=2022-10-22}} and Fernando Tatís Jr. of the San Diego Padres in 2022.{{cite news|url=https://www.espn.com/mlb/story/_/id/34390702/san-diego-padres-star-fernando-tatis-jr-suspended-80-games-ped-violation|title=San Diego Padres star Fernando Tatis Jr. suspended 80 games after testing positive for PED| vauthors = Passan J |date=12 August 2022|work=ESPN.com|access-date=12 August 2022}} 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.{{cite web | vauthors = Passan J | work = ESPN | url=https://www.espn.com.au/mlb/story/_/id/34390702/san-diego-padres-star-fernando-tatis-jr-suspended-80-games-ped-violation | title=Padres' Tatis banned 80 games for PED violation | date=12 August 2022 }}
In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.{{Cite web | url=https://www.nrk.no/sport/advokat_-_-johaug-fikk-hele-pakken-1.13182815 |title = Advokat: – Johaug fikk hele pakken | trans-title = Lawyer: - Johaug got the whole package | language = no |date = 2016-10-17 | work = NRK }}{{Cite web | vauthors = Tingve PM, Skaug TR | date = 13 October 2016 | url=http://www.dagbladet.no/sport/slik-hevder-johaug-a-ha-fatt-i-seg-det-forbudte-stoffet/63962006 |title = Slik hevder Johaug å ha fått i seg det forbudte stoffet | trans-title = This is how Johaug claims to have ingested the prohibited substance | language = no | work = Dagbladet }}{{Cite web |url= http://nordic.businessinsider.com/therese-johaug-tested-positive-for-doping----norwegian-ski-federation-cancels-huge-kick-off-2016-10/ | vauthors = Carlström V | work = Insider Inc | publisher = Bonnier Business Media Sweden AB |title=World's best cross-country skier Therese Johaug hit by new Norwegian doping scandal |date=October 13, 2016 |access-date=2016-10-18 |archive-url=https://web.archive.org/web/20190126115240/http://nordic.businessinsider.com/therese-johaug-tested-positive-for-doping----norwegian-ski-federation-cancels-huge-kick-off-2016-10/ |archive-date=2019-01-26 |url-status=dead }}
Italian tennis player Jannik Sinner tested positive for clostebol in two different urine samples on 8 March and 10 March 2024.{{cite web |agency=Associated Press |date=August 20, 2024 |title=Jannik Sinner, world No. 1, tested positive for a steroid twice but will not be suspended |url=https://www.tennis.com/news/articles/tennis-star-jannik-sinner-tested-positive-for-a-steroid-twice-but-will-not-be-suspended |access-date=August 20, 2024 |work = Tennis.com}} The International Tennis Integrity Agency (ITIA) found Sinner was inadvertently contaminated with the substance by his physiotherapist who had been applying the healing spray Trofodermin, available over-the counter in Italy, to treat a cut on his own hand and had then carried out treatments on Sinner.{{Cite web |date=20 August 2024 |title=Jannik Sinner cleared of any wrongdoing after twice testing positive for banned substance in March |url=https://www.bbc.co.uk/sport/tennis/articles/cq5d3nl1pd9o |access-date=2024-08-21 |website=BBC Sport |language=en-GB}} Sinner was stripped of $325,000 in prize money and 400 ranking points earned at the Indian Wells Open, but wasn't suspended initially because an independent tribunal ruled that it was not intentional.{{Cite web |date=19 August 2024 |title=Decision of independent tribunal: International Tennis Integrity Agency (ITIA) vs. Jannik Sinner (SR/250/2024) |url=https://www.itia.tennis/media/yzgd3xoz/240819-itia-v-sinner.pdf | work = Sport Resolutions }} However, the World Anti-Doping Agency (WADA) announced in February 2025 they entered a "case resolution agreement" with Sinner.{{Cite web |date=2024-09-28 |title=WADA to appeal Sinner doping verdict, seeks ban |url=https://www.espn.co.uk/tennis/story/_/id/41487305/wada-appeal-jannik-sinner-doping-verdict-seek-suspension |access-date=2025-02-16 |website=ESPN.com |language=en}}{{Cite web |date=2024-09-28 |title=Jannik Sinner: Wada appeals to Cas over exoneration after failed drug tests verdict |url=https://www.bbc.com/sport/tennis/articles/c4gr8433527o |access-date=2025-02-16 |website=BBC Sport |language=en-GB}} WADA accepted the cause and explanation of the positive test but stated "an athlete bears responsibility for the entourage’s negligence". A three-month suspension was handed down with Sinner being ineligible from tennis competition from 9 February to 4 May 2025.{{Cite web |date=2025-02-15 |title=Jannik Sinner: Italian banned for three months for doping |url=https://www.bbc.com/sport/tennis/articles/cj48rn79kego |access-date=2025-02-16 |website=BBC Sport |language=en-GB}}{{Cite news |date=2025-02-15 |title=Sinner accepts three-month doping ban after striking deal with WADA |url=https://www.abc.net.au/news/2025-02-15/jannik-sinner-accepts-three-month-doping-ban-wada-deal/104941608 |access-date=2025-02-16 |work=ABC News |language=en-AU}}
=Regulation=
In the U.S., clostebol is listed as a Schedule III controlled substance, 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
{{Reflist|2}}
{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}