Trimethyltrienolone

[1][2][3] Due to its close relation to metribolone (methyltrienolone), it is thought that TMT may produce hepatotoxicity.[4] TMT is a selective and highly potent competitive antagonist of the androgen receptor (AR) with very low intrinsic/partial androgenic activity and no estrogenic, antiestrogenic, progestogenic, or antimineralocorticoid activity.[5][6] The drug is a derivative of the extremely potent androgen/anabolic steroid metribolone (R-1881; 17α-methyltrenbolone),[6][7] and has been reported to possess only about 4-fold lower affinity for the AR in comparison.[9] The AR weak partial agonistic activity of TMT is comparable to that of cyproterone acetate.[5][17][18][19][20] The drug was under investigation by Roussel Uclaf for potential medical use, but was abandoned in favor of nonsteroidal antiandrogens like flutamide and nilutamide due to their comparative advantage of a complete lack of androgenicity.
Drug classSteroidal antiandrogenATC codeIUPAC nameCAS NumberChemSpiderCompTox DashboardFormulaMolar massSMILESantiandrogenscientific researchmetribolonehepatotoxicityselectivepotentcompetitiveantagonistandrogen receptorintrinsicpartialandrogenicestrogenicantiestrogenicprogestogenicantimineralocorticoidderivativeandrogenanabolic steroidaffinitydihydrotestosteronein vitrocyproterone acetateTestosterone5α-DihydrotestosteroneligandsprogesteronealdosteroneList of steroidal antiandrogenssyntheticestranesteroid19-nortestosteronetrenboloneandrogensanabolic steroidsRoussel UclafFrancebenorteronecyproteronenonsteroidal antiandrogensflutamidenilutamidemodulators4-Androstenediol4-Dehydroepiandrosterone (4-DHEA)4-Hydroxytestosterone5-Androstenedione11-Ketotestosterone11β-HydroxyandrostenedioneAdrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)Androstenediol (5-androstenediol)Androstenediol 3β-acetateAndrostenediol 17β-acetateAndrostenediol diacetateAndrostenediol dipropionateAndrostenedione (4-androstenedione)AtamestaneBoldenoneBoldenone undecylenateBoldione (1,4-androstadienedione)ClostebolClostebol acetateClostebol caproateClostebol propionateCloxotestosteroneCloxotestosterone acetateDehydroandrosteroneDHEA (androstenolone, prasterone; 5-DHEA)DHEA enanthate (prasterone enanthate)DHEA sulfateExemestaneFormestanePlomestaneQuinboloneSilandrone+dutasteridePolytestosterone phloretin phosphate1-Androstenediol1-Androstenedione1-Androsterone (1-andro, 1-DHEA)1-Testosterone3α-Androstanediol5α-Androst-2-en-17-one7β-Hydroxyepiandrosterone11-KetodihydrotestosteroneAndrosteroneBolazineBolazine capronateDihydrofluoxymesteroneDihydrotestosterone (DHT)androstanolone, stanoloneDrostanoloneDrostanolone propionateEpiandrosteroneEpitiostanolMepitiostaneMesaboloneMesteroloneMesterolone cipionateMethyldiazinolNisterimeNisterime acetateProstanozolStenboloneStenbolone acetateTestifenon (testiphenon, testiphenone)7α-Methyl-19-norandrostenedione (MENT dione, trestione)11β-Methyl-19-nortestosterone11β-Methyl-19-nortestosterone dodecylcarbonate19-Nor-5-androstenediol19-Nor-5-androstenedione19-NordehydroepiandrosteroneBolandiolBolandiol dipropionateBolandione (19-nor-4-androstenedione)Bolmantalate (nandrolone adamantoate)DienedioneDienoloneDimethandroloneDimethandrolone buciclateDimethandrolone dodecylcarbonateDimethandrolone undecanoateLS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)Methoxydienone (methoxygonadiene)NandroloneNorclostebolNorclostebol acetateNormethandrone (methylestrenolone, normethisterone)OxaboloneOxabolone cipionate (oxabolone cypionate)Trenbolone acetateTrenbolone enanthateTrenbolone hexahydrobenzylcarbonateTrenbolone undecanoateTrendioneTrestolone (MENT)Trestolone acetateTrestolone enanthate5α-Dihydronandrolone19-NorandrosteroneBolasteroneCalusteroneChlorodehydromethylandrostenediol (CDMA)Chlorodehydromethyltestosterone (CDMT)Chloromethylandrostenediol (CMA)EnestebolEthyltestosteroneFluoxymesteroneFormeboloneHydroxystenozoleMetandienone (methandrostenolone)Methandriol (methylandrostenediol)Methandriol bisenanthoyl acetateMethandriol diacetateMethandriol dipropionateMethandriol propionateMethylclostebol (chloromethyltestosterone)Methyltestosterone+esterified estrogensMethyltestosterone 3-hexyl etherOxymesteronePenmesterolTiomesteroneAndroisoxazoleDesoxymethyltestosteroneFurazabolMebolazine (dimethazine)MestanoloneMetenoloneMetenolone acetateMetenolone enanthateMethasteroneMethyl-1-testosteroneMethylepitiostanolMethylstenboloneOxandroloneOxymetholoneStanozololBolenolDimethyldienoloneDimethyltrienoloneEthyldienoloneEthylestrenolMethyldienoloneMethylhydroxynandrolone (MOHN, MHN)MiboleroneNorboletoneNorethandrolonePropetandrolRU-2309Tetrahydrogestrinone5α-Dihydronorethandrolone5α-DihydronormethandroneNorvinisterone (vinylnortestosterone)VinyltestosteroneDanazolEthinylandrostenediolEthandrostateEthisterone (ethynyltestosterone)17α-Ethynyl-3α-androstanediol17α-Ethynyl-3β-androstanediolDihydroethisteroneΔ4-TiboloneDesogestrelEtonogestrelEtynodiolEtynodiol diacetateGestodeneGestrinoneLevonorgestrelLevonorgestrel esterslevonorgestrel butanoateLynestrenolLynestrenol phenylpropionateNorethisteroneNorethisterone estersnorethisterone acetatenorethisterone enanthateNorgestrelNorgestrienoneQuingestanolQuingestanol acetateTibolone5α-Dihydrolevonorgestrel5α-Dihydronorethisterone6α-MethylprogesteroneMedroxyprogesterone acetateMegestrol acetate3-Keto-5α-abiraterone5α-AndrostaneAlternariolCl-4AS-1DrupanolTrilostaneZM-182345ACP-105AC-262,536AcetothiolutamideAcetoxolutamideAndarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)BMS-564,929Enobosarm (ostarine, MK-2866, GTx-024, S-22)GLPG-0492GSK2881078GSK-4336ALG121071 (LGD-121071)LGD-2226LGD-2941 (LGD-122941)LGD-3303LGD-4033JNJ-26146900JNJ-28330835JNJ-37654032OPK-88004 (LY-2452473, TT-701)PF-06260414RU-59063S-40503VosilasarmMK-0773TFM-4AS-17α-Thioprogesterone7α-Thiospironolactone7α-Thiomethylspironolactone11α-Hydroxyprogesterone15β-Hydroxycyproterone acetateAbirateroneAbiraterone acetateAllyltestosteroneCanrenoic acidCanrenoneChlormadinone acetateClascoteroneClometeroneCyproheptadineDelanteroneDelmadinone acetateDicirenoneDienogestDrospirenoneDU-41165EdogestroneEM-5854EpitestosteroneGaleteroneGuggulsteroneMedrogestoneMespirenoneMetogestMexrenoneMifepristoneNomegestrol acetateNordinoneOsateroneOsaterone acetateOxendolonePotassium canrenoatePromegestoneProrenoneRosteroloneSC-5233 (spirolactone)SpironolactoneSpirorenoneSpiroxasoneTopteroneTrimegestoneZanoterone5N-BicalutamideApalutamideAtraric acidBakuchiolBavdegalutamideBicalutamideBisphenolsbisphenol Abisphenol Fbisphenol SBMS-641988CimetidineCioteronelCyanonilutamideDarolutamidep,p’-DDEDieldrinEndosulfanEnzalutamideEPI-001FenarimolHydroxyflutamideInocoteroneInocoterone acetateKetoconazoleKetodarolutamideLavender oilLG-120907LinuronMasofanitenMethiocarbN-DesmethylapalutamideN-DesmethylenzalutamidePentomonePhenothrinProchlorazProcymidoneProxalutamidePyrilutamideRalaniten (EPI-002)Ralaniten acetate (EPI-506)RD-162RezvilutamideRU-22930RU-56187RU-57073RU-58642RU-58841SeviteronelThalidomideTopilutamide (fluridil)Valproic acidVinclozolinGPRC6ACationsaluminiumcalciumgadoliniummagnesiumstrontiumEstradiolL-α-Amino acidsL-arginineL-lysineL-ornithineOsteocalcinList of androgens and anabolic steroids