Clostebol |
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Other names | Chlorotestosterone; 4-Chlorotestosterone; 4-Chloroandrost-4-en-17β-ol-3-one |
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Drug class | Androgen; Anabolic steroid |
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Legal status |
- BR: Class C5 (Anabolic steroids)[1]
- CA: Schedule IV
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(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
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CAS Number | |
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ChEMBL | |
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CompTox Dashboard (EPA) | |
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ECHA InfoCard | 100.012.849 |
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Formula | C19H27ClO2 |
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Molar mass | 322.87 g·mol−1 |
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3D model (JSmol) | |
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O=C4C(\Cl)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
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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
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NY (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]
Medical uses
Clostebol acetate ointment has ophthalmological and dermatological use.[5] 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.[6]
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.[7]
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,[8] Dee Gordon of the Miami Marlins in 2016,[9] Olympic athlete Viktoria Orsi Toth in 2016,[10] Serie A soccer player José Luis Palomino of Club Atalanta,[11] Orlando Galo from C.S. Herediano in 2022,[12] and Fernando Tatís Jr. of the San Diego Padres in 2022.[13] 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.[14]
In 2016, urinalysis resulted in Therese Johaug testing positive for clostebol.[15][16][17]
Italian tennis player Jannik Sinner tested positive for clostebol in two different urine samples on 8 March and 10 March 2024.[18] 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.[19] 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.[18][19][20] However, the World Anti-Doping Agency (WADA) announced in February 2025 they entered a "case resolution agreement" with Sinner.[21][22] 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.[23][24]
Regulation
In the U.S., clostebol is listed as a Schedule III controlled substance,[7] meaning the U.S. federal government considers it to have a potential for abuse as well as a currently accepted medical use.
See also
- Chlorodehydromethyltestosterone
- Methylclostebol
References
- ↑ 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.
- ↑ Maccaroni E, Mele A, Del Rosso R, Malpezzi L (August 2011). "Clostebol acetate". Acta Crystallographica Section E: Structure Reports Online. 67 (Pt 8): o1952 – o1953. Bibcode:2011AcCrE..67o1952M. doi:10.1107/S1600536811026560. PMC 3212337. PMID 22090994.
- ↑ de la Torre X, Colamonici C, Iannone M, Jardines D, Molaioni F, Botrè F (November 2020). "Detection of clostebol in sports: Accidental doping?". Drug Testing and Analysis. 12 (11–12): 1561–1569. doi:10.1002/dta.2951. PMID 33119965.
- 1 2 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 (11 July 2016). "Phillies say they will welcome Stumpf back after drug suspension". Archived from the original on 17 August 2016.
- ↑ "Marlins 2B Dee Gordon suspended 80 games after PEDs violation". ESPN. 29 April 2016.
- ↑ "Rio 2016, beach volley: conferma di doping per Viktoria Orsi Toth" [Rio 2016, beach volleyball: confirmation of doping for Viktoria Orsi Toth]. Panorama (in Italian). 3 August 2016. Retrieved 3 August 2016.
- ↑ Campanale S (26 July 2022). "Report Atalanta's Palomino Fails Doping Test".
- ↑ "World Cup doping: Costa Rica's Galo positive for steroid". AP. 22 October 2022.
- ↑ 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.
- ↑ Passan J (12 August 2022). "Padres' Tatis banned 80 games for PED violation". ESPN.
- ↑ "Advokat: – Johaug fikk hele pakken" [Lawyer: - Johaug got the whole package]. NRK (in Norwegian). 17 October 2016.
- ↑ Tingve PM, Skaug TR (13 October 2016). "Slik hevder Johaug å ha fått i seg det forbudte stoffet" [This is how Johaug claims to have ingested the prohibited substance]. Dagbladet (in Norwegian).
- ↑ Carlström V (13 October 2016). "World's best cross-country skier Therese Johaug hit by new Norwegian doping scandal". Insider Inc. Bonnier Business Media Sweden AB. Archived from the original on 26 January 2019. Retrieved 18 October 2016.
- 1 2 "Jannik Sinner, world No. 1, tested positive for a steroid twice but will not be suspended". Tennis.com. Associated Press. 20 August 2024. Retrieved 20 August 2024.
- 1 2 "Jannik Sinner cleared of any wrongdoing after twice testing positive for banned substance in March". BBC Sport. 20 August 2024. Retrieved 21 August 2024.
- ↑ "Decision of independent tribunal: International Tennis Integrity Agency (ITIA) vs. Jannik Sinner (SR/250/2024)" (PDF). Sport Resolutions. 19 August 2024.
- ↑ "WADA to appeal Sinner doping verdict, seeks ban". ESPN.com. 28 September 2024. Retrieved 16 February 2025.
- ↑ "Jannik Sinner: Wada appeals to Cas over exoneration after failed drug tests verdict". BBC Sport. 28 September 2024. Retrieved 16 February 2025.
- ↑ "Jannik Sinner: Italian banned for three months for doping". BBC Sport. 15 February 2025. Retrieved 16 February 2025.
- ↑ "Sinner accepts three-month doping ban after striking deal with WADA". ABC News. 15 February 2025. Retrieved 16 February 2025.
Androgens and antiandrogens |
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Androgens (incl. AASTooltip anabolic–androgenic steroid) | ARTooltip Androgen receptor agonists |
- Testosterone derivatives: Androstenediol dipropionate
- Boldenone undecylenate
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone acetate
- Prasterone (dehydroepiandrosterone, DHEA)
- Prasterone enanthate (DHEA enanthate)
- Prasterone sulfate (DHEA sulfate)
- Quinbolone
- Testosterone#
- Testosterone esters (e.g., testosterone cypionate, testosterone enanthate, testosterone propionate, testosterone undecanoate, testosterone ester mixtures (Deposterona, Omnadren, Sustanon, Testoviron Depot))
- Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
- Androstanolone esters
- Bolazine capronate
- Drostanolone propionate (dromostanolone propionate)
- Epitiostanol
- Mepitiostane
- Mesterolone
- Metenolone acetate (methenolone acetate)
- Metenolone enanthate (methenolone enanthate)
- Stenbolone acetate
- 19-Nortestosterone derivatives: Bolandiol dipropionate
- Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
- Norclostebol
- Norclostebol acetate
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone acetate
- Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)
- 17α-Alkylated testosterone derivatives: Bolasterone
- Calusterone
- Chlorodehydromethyltestosterone (CDMT)
- Fluoxymesterone
- Formebolone
- Metandienone (methandienone, methandrostenolone)
- Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol dipropionate
- Methandriol propionate
- Methyltestosterone
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone (thiomesterone)
- 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
- Oxandrolone
- Oxymetholone
- Stanozolol
- 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
- Mibolerone
- Norethandrolone
- Normethandrone (methylestrenolone, normethisterone)
- Propetandrol (propethandrol)
- 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- 17α-Ethynyltestosterone derivatives: Danazol
- Gestrinone
- Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), lynestrenol, norgestrienone)
- Tibolone
- Progesterone derivatives: Medroxyprogesterone acetate
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Progonadotropins |
- Antiestrogens (e.g., tamoxifen, clomifene)
- GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
- Gonadotropins (e.g., LHTooltip luteinizing hormone, hCGTooltip human chorionic gonadotropin)
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Antiandrogens | ARTooltip Androgen receptor antagonists |
- Steroidal: Abiraterone acetate +niraparib
- Canrenone
- Chlormadinone acetate
- Cyproterone acetate
- Delmadinone acetate
- Dienogest
- Drospirenone
- Medrogestone
- Megestrol acetate
- Nomegestrol acetate
- Osaterone acetate
- Oxendolone
- Potassium canrenoate
- Spironolactone
- Nonsteroidal: Apalutamide
- Bicalutamide
- Cimetidine
- Darolutamide
- Enzalutamide
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Topilutamide (fluridil)
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Steroidogenesis inhibitors | 5α-Reductase |
- Alfatradiol
- Dutasteride
- Epristeride
- Finasteride
- Saw palmetto extract
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Others |
- Abiraterone acetate +niraparib
- Aminoglutethimide
- Bifluranol
- Cyproterone acetate
- Flutamide
- Ketoconazole
- Nilutamide
- Seviteronel†
- Spironolactone
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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)
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Others |
- Androstenedione immunogens: Androvax (androstenedione albumin)
- Ovandrotone albumin (Fecundin)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
- See also
- Androgen receptor modulators
- Estrogens and antiestrogens
- Progestogens and antiprogestogens
- List of androgens/anabolic steroids
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Androgen receptor modulators |
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ARTooltip Androgen receptor | Agonists |
- Testosterone derivatives: 4-Androstenediol
- 4-Dehydroepiandrosterone (4-DHEA)
- 4-Hydroxytestosterone
- 4,17α-Dimethyltestosterone
- 5-Androstenedione
- 11-Ketotestosterone
- 11β-Hydroxyandrostenedione
- Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
- Androstenediol (5-androstenediol)
- Androstenediol 3β-acetate
- Androstenediol 17β-acetate
- Androstenediol diacetate
- Androstenediol dipropionate
- Androstenedione (4-androstenedione)
- Atamestane
- Boldenone
- Boldione (1,4-androstadienedione)
- Clostebol
- Clostebol acetate
- Clostebol caproate
- Clostebol propionate
- Cloxotestosterone
- Cloxotestosterone acetate
- Dehydroandrosterone
- DHEA (androstenolone, prasterone; 5-DHEA)
- DHEA enanthate (prasterone enanthate)
- DHEA sulfate
- Exemestane
- Formestane
- Plomestane
- Quinbolone
- Silandrone
- Testosterone# (+dutasteride)
- Testosterone esters
- Polytestosterone phloretin phosphate
- 5α-Dihydrotestosterone derivatives: 1-Androstenediol
- 1-Androstenedione
- 1-Androsterone (1-andro, 1-DHEA)
- 1-Testosterone
- 3α-Androstanediol
- 5α-Androst-2-en-17-one
- 7β-Hydroxyepiandrosterone
- 11-Ketodihydrotestosterone
- Androsterone
- Bolazine
- Dihydroethyltestosterone
- Dihydrofluoxymesterone
- Dihydromethylandrostenediol
- Dihydrotestosterone (DHT) (androstanolone, stanolone)
- Dihydrotestosterone esters
- Drostanolone
- Epiandrosterone
- Epitiostanol
- Mepitiostane
- Mesabolone
- Mesterolone
- Methyldiazinol
- Nisterime
- Prostanozol
- Stenbolone
- Testifenon (testiphenon, testiphenone)
- 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
- 11β-Methyl-19-nortestosterone
- 11β-Methyl-19-nortestosterone dodecylcarbonate
- 19-Nor-5-androstenediol
- 19-Nor-5-androstenedione
- 19-Nordehydroepiandrosterone
- Bolandiol
- Bolandione (19-nor-4-androstenedione)
- Bolmantalate (nandrolone adamantoate)
- Dienedione
- Dienolone
- Dimethandrolone
- Dimethandrolone buciclate
- Dimethandrolone dodecylcarbonate
- Dimethandrolone undecanoate
- LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)
- Methoxydienone (methoxygonadiene)
- Nandrolone
- Norclostebol
- Normethandrone (methylestrenolone, normethisterone)
- Oxabolone
- Oxabolone cipionate (oxabolone cypionate)
- Trenbolone
- Trenbolone acetate
- Trenbolone enanthate
- Trenbolone hexahydrobenzylcarbonate
- Trenbolone undecanoate
- Trendione
- Trestolone (MENT)
- Trestolone acetate
- Trestolone enanthate
- 5α-Dihydro-19-nortestosterone derivatives: 5α-Dihydronandrolone
- 5α-Dihydrotrestolone
- 19-Norandrosterone
- 17α-Alkylated testosterone derivatives: Bolasterone
- Calusterone
- Chlorodehydromethylandrostenediol (CDMA)
- Chlorodehydromethyltestosterone (CDMT)
- Chloromethylandrostenediol (CMA)
- Enestebol
- Ethyltestosterone
- Fluoxymesterone
- Formebolone
- Hydroxystenozole
- Metandienone (methandrostenolone)
- Methandriol (methylandrostenediol)
- Methandriol bisenanthoyl acetate
- Methandriol diacetate
- Methandriol dipropionate
- Methandriol propionate
- Methylclostebol (chloromethyltestosterone)
- Methyltestosterone (+esterified estrogens)
- Methyltestosterone 3-hexyl ether
- Oxymesterone
- Penmesterol
- Tiomesterone
- 17α-Alkylated 5α-dihydrotestosterone derivatives: Androisoxazole
- Desoxymethyltestosterone
- Furazabol
- Mebolazine (dimethazine)
- Mestanolone
- Metenolone
- Metenolone acetate
- Metenolone enanthate
- Methasterone
- Methyl-1-testosterone
- Methylepitiostanol
- Methylstenbolone
- Oxandrolone
- Oxymetholone
- Stanozolol
- 17α-Alkylated 19-nortestosterone derivatives: Bolenol
- Dimethyldienolone
- Dimethyltrienolone
- Ethyldienolone
- Ethylestrenol
- Methyldienolone
- Methylhydroxynandrolone (MOHN, MHN)
- Metribolone
- Mibolerone
- Norboletone
- Norethandrolone
- Propetandrol
- RU-2309
- Tetrahydrogestrinone
- 17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
- 5α-Dihydronormethandrone
- 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
- 17α-Vinyl-19-nortestosterone derivatives: Vinyltestosterone
- 17α-Ethynyltestosterone derivatives: Danazol
- Ethinylandrostenediol
- Ethisterone (ethynyltestosterone)
- 5α-Dihydro-17α-ethynyltestosterone derivatives: 17α-Ethynyl-3α-androstanediol
- 17α-Ethynyl-3β-androstanediol
- Dihydroethisterone
- 17α-Ethynyl-19-nortestosterone derivatives: Δ4-Tibolone
- Desogestrel
- Etonogestrel
- Etynodiol
- Gestodene
- Gestrinone
- Levonorgestrel
- Levonorgestrel esters (e.g., levonorgestrel butanoate)
- Lynestrenol
- Lynestrenol phenylpropionate
- Norethisterone
- Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
- Norgestrel
- Norgestrienone
- Quingestanol
- Tibolone
- 5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
- 5α-Dihydronorethisterone
- Progesterone derivatives: 6α-Methylprogesterone
- Medroxyprogesterone acetate
- Megestrol acetate
- Others/unsorted: 3-Keto-5α-abiraterone
- 5α-Androstane
- Alternariol
- Cl-4AS-1
- Drupanol
- Trilostane
- ZM-182345
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SARMsTooltip Selective androgen receptor modulator |
- Nonsteroidal: 198RL26
- ACP-105
- AC-262,536
- Acetothiolutamide
- Acetoxolutamide
- Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
- BMS-564,929
- DTIB
- Enobosarm (ostarine, MK-2866, GTx-024, S-22)
- FTBU-1
- GLPG-0492
- GSK2881078
- GSK-4336A
- GSK-8698
- LG121071 (LGD-121071)
- LGD-2226
- LGD-2941 (LGD-122941)
- LGD-3303
- LGD-4033
- LY305
- JNJ-26146900
- JNJ-28330835
- JNJ-37654032
- OPK-88004 (LY-2452473, TT-701)
- ORM-11984
- PF-06260414
- R-1
- RU-59063
- S-1
- S-23
- S-40503
- S-101479
- Vosilasarm
- Steroidal: EM-9017
- MK-0773
- TFM-4AS-1
- YK-11
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Antagonists | |
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GPRC6A | |
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- See also
- Receptor/signaling modulators
- Androgens and antiandrogens
- Estrogen receptor modulators
- Progesterone receptor modulators
- List of androgens and anabolic steroids
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