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Clostebol

January 01, 1970

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
Clinical data
Other namesChlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Identifiers
  • (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 Y
PubChem CID
  • 68947
DrugBank
  • DB01521 Y
ChemSpider
  • 62171 Y
UNII
  • Z7D4G976SH
KEGG
  • D07731 Y
ChEMBL
  • ChEMBL2106571 N
CompTox Dashboard (EPA)
  • DTXSID5046192
ECHA InfoCard100.012.849
Chemical and physical data
FormulaC19H27ClO2
Molar mass322.87 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Y
  • Key:KCZCIYZKSLLNNH-FBPKJDBXSA-N Y
 NY (what is this?)  (verify)

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 edit

Clostebol acetate ointment has ophthalmological and dermatological use.[5]

Side effects edit

See also: Anabolic steroid § Adverse effects

Chemistry edit

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 edit

Nutritional supplements edit

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 edit

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 edit

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 edit

References edit

  1. ^ 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). from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 265–. ISBN 978-3-88763-075-1.
  3. ^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.
  4. ^ "Doping for Gold: The State-Sponsored Doping Program". PBS. 2011-06-13.
  5. ^ 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.
  6. ^ 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.
  7. ^ Breen M (July 11, 2016). "Phillies say they will welcome Stumpf back after drug suspension".
  8. ^ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN. 2016-04-29.
  9. ^ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth – Panorama" (in Italian). 2016-08-03. Retrieved 2016-08-03.
  10. ^ Campanale S (2022-07-26). "Report Atalanta's Palomino Fails Doping Test".
  11. ^ 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.
  12. ^ "Padres' Tatis banned 80 games for PED violation". 12 August 2022.
  13. ^ "Advokat: – Johaug fikk hele pakken". 2016-10-17.
  14. ^ "Slik hevder Johaug å ha fått i seg det forbudte stoffet". 2016-10-13.
  15. ^ . October 13, 2016. Archived from the original on 2019-01-26. Retrieved 2016-10-18.

January 01, 1970
clostebol, inntooltip, international, nonproprietary, name, also, known, chlorotestosterone, usually, ester, clostebol, acetate, synthetic, anabolic, androgenic, steroid, chloro, derivative, natural, hormone, testosterone, chlorination, prevents, conversion, d. 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 ClostebolClinical dataOther namesChlorotestosterone 4 Chlorotestosterone 4 Chloroandrost 4 en 17b ol 3 oneDrug classAndrogen Anabolic steroidATC codeNoneLegal statusLegal statusBR Class C5 Anabolic steroids 1 CA Schedule IVIdentifiersIUPAC 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 oneCAS Number1093 58 9 YPubChem CID68947DrugBankDB01521 YChemSpider62171 YUNIIZ7D4G976SHKEGGD07731 YChEMBLChEMBL2106571 NCompTox Dashboard EPA DTXSID5046192ECHA InfoCard100 012 849Chemical and physical dataFormulaC 19H 27Cl O 2Molar mass322 87 g mol 13D model JSmol Interactive imageSMILES O C4C Cl C2 C C H 1CC C 3 C H O CC C H 3 C H 1CC2 C C CC4InChI 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 YKey KCZCIYZKSLLNNH FBPKJDBXSA N Y N Y what is this verify 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 Contents 1 Medical uses 2 Side effects 3 Chemistry 4 Society and culture 4 1 Nutritional supplements 4 2 Publicized abuse cases 4 3 Regulation 5 See also 6 ReferencesMedical uses editClostebol acetate ointment has ophthalmological and dermatological use 5 Side effects editSee also Anabolic steroid Adverse effectsChemistry editSee also List of androgens anabolic steroids Clostebol also known as 4 chlorotestosterone or as 4 chloroandrost 4 en 17b 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 editNutritional supplements edit A related anabolic steroid methylclostebol is a common additive in so called dietary supplements generally listed in the convoluted form 4 chloro 17a methyl androst 4 en 17b ol 3 one 6 Publicized abuse cases edit 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 Jose Luis Palomino of Club Atalanta and Fernando Tatis Jr of the San Diego Padres in 2022 10 11 Tatis 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 2022In 2016 urinalysis resulted in Therese Johaug testing positive for clostebol 13 14 15 Regulation edit 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 editChlorodehydromethyltestosterone MethylclostebolReferences edit Anvisa 2023 03 31 RDC Nº 784 Listas de Substancias Entorpecentes Psicotropicas 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 Diario Oficial da Uniao published 2023 04 04 Archived from the original on 2023 08 03 Retrieved 2023 08 15 Index Nominum 2000 International Drug Directory Taylor amp 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 a ha fatt 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 Retrieved from https en wikipedia org w index php title Clostebol amp oldid 1205720010, wikipedia, wiki, book, books, library,

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