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Kembali ke Ensiklopedia Arsip Wikipedia Indonesia TFM-4AS-1 TFM-4AS-1Abandoned drug Pharmaceutical compoundTFM-4AS-1Clinical dataOther namesN-[2-(Trifluoromethyl)phenyl]-3-oxo-4-aza-4-methyl-5α-androst-1-en-17α-carboxamideIdentifiers IUPAC name (1S,3aS,3bS,5aR,9aR,9bS,11aS)-6,9a,11a-trimethyl-7-oxo-N-[2-(trifluoromethyl)phenyl]-2,3,3a,3b,4,5,5a,9b,10,11-decahydro-1H-indeno[5,4-f]quinoline-1-carboxamide CAS Number188589-61-9PubChem CID90488882ChemSpider26232144Chemical and physical dataFormulaC27H33F3N2O2Molar mass474.568 g·mol−13D model (JSmol)Interactive image SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC4=CC=CC=C4C(F)(F)F)CCC5[C@@]3(C=CC(=O)N5C)C InChI InChI=1S/C27H33F3N2O2/c1-25-14-12-18-16(8-11-22-26(18,2)15-13-23(33)32(22)3)17(25)9-10-20(25)24(34)31-21-7-5-4-6-19(21)27(28,29)30/h4-7,13,15-18,20,22H,8-12,14H2,1-3H3,(H,31,34)/t16-,17-,18-,20+,22?,25-,26+/m0/s1Key:YFBLEKKYWFJKBP-HRVOXWHZSA-N TFM-4AS-1 is a dual selective androgen receptor modulator (SARM) and 5α-reductase inhibitor.[1][2] It is a potent and selective partial agonist (Emax = 55%) of the androgen receptor (IC50 = 30 nM) and inhibitor of 5α-reductase types I and II (IC50 = 2 and 3 nM, respectively).[1][2] TFM-4AS-1 shows tissue-selective androgenic effects; it promotes the accumulation of bone and muscle mass and has reduced effects in reproductive tissues and sebaceous glands.[2] In an animal study, TFM-4AS-1 stimulated sebaceous gland formation only 31% as much as dihydrotestosterone (DHT) at doses that were as anabolic or more so than DHT.[3][2] In addition, TFM-4AS-1 only weakly promoted growth of the prostate gland and it partially antagonized the actions of DHT in the seminal vesicles and endogenous androgens in the prostate gland.[2] Structurally, TFM-4AS-1 is a 4-azasteroid.[1] A structurally related and more advanced version of TFM-4AS-1, MK-0773, was developed and pursued for potential pharmaceutical use.[3] See also Cl-4AS-1 MK-0773 MK-4541 YK-11 References 1 2 3 Tolman RL, Sahoo SP, Bakshi RK, Gratale D, Patel G, Patel S, Toney J, Chang B, Harris GS (1997). "4-Methyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-N-aryl-carboxamides: an approach to combined androgen blockade [5alpha-reductase inhibition with androgen receptor binding in vitro]". J. Steroid Biochem. Mol. Biol. 60 (5–6): 303–9. doi:10.1016/s0960-0760(96)00199-9. PMID 9219921. S2CID 54405031. 1 2 3 4 5 Schmidt A, Harada S, Kimmel DB, Bai C, Chen F, Rutledge SJ, Vogel RL, Scafonas A, Gentile MA, Nantermet PV, McElwee-Witmer S, Pennypacker B, Masarachia P, Sahoo SP, Kim Y, Meissner RS, Hartman GD, Duggan ME, Rodan GA, Towler DA, Ray WJ (2009). "Identification of anabolic selective androgen receptor modulators with reduced activities in reproductive tissues and sebaceous glands". J. Biol. Chem. 284 (52): 36367–76. doi:10.1074/jbc.M109.049734. PMC 2794752. PMID 19846549. 1 2 Zhang X, Sui Z (February 2013). "Deciphering the selective androgen receptor modulators paradigm". Expert Opin Drug Discov. 8 (2): 191–218. doi:10.1517/17460441.2013.741582. PMID 23231475. S2CID 2584722. vteAndrogen receptor modulatorsARTooltip Androgen receptorAgonists 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 Boldenone undecylenate 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 Bolazine capronate Dihydroethyltestosterone Dihydrofluoxymesterone Dihydromethylandrostenediol Dihydrotestosterone (DHT) (androstanolone, stanolone) Dihydrotestosterone esters Drostanolone Drostanolone propionate Epiandrosterone Epitiostanol Mepitiostane Mesabolone Mesterolone Mesterolone cipionate Methyldiazinol Nisterime Nisterime acetate Prostanozol Stenbolone Stenbolone acetate 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 Bolandiol dipropionate 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 Nandrolone esters Norclostebol Norclostebol acetate 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 Ethandrostate 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 Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g., levonorgestrel butanoate) Lynestrenol Lynestrenol phenylpropionate Norethisterone Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate) Norgestrel Norgestrienone Quingestanol Quingestanol acetate 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 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 S42 TFM-4AS-1 YK-11 Antagonists Steroidal: 7α-Thioprogesterone 7α-Thiospironolactone 7α-Thiomethylspironolactone 11α-Hydroxyprogesterone 15β-Hydroxycyproterone acetate Abiraterone Abiraterone acetate Allyltestosterone Benorterone BOMT Canrenoic acid Canrenone Chlormadinone acetate Clascoterone Clometerone Cyproheptadine Cyproterone Cyproterone acetate Delanterone Delmadinone acetate Dicirenone Dienogest Drospirenone DU-41165 Edogestrone EM-4350 EM-5854 EM-5855 EM-6537 Epitestosterone Galeterone Guggulsterone Ludaterone Medrogestone Megestrol acetate Mespirenone Metogest Mexrenone Mifepristone Nomegestrol acetate Nordinone Osaterone Osaterone acetate Oxendolone Potassium canrenoate Promegestone Prorenone Rosterolone RU-15328 SC-5233 (spirolactone) Spironolactone Spirorenone Spiroxasone Topterone Trimegestone Trimethyltrienolone (R-2956) Zanoterone Nonsteroidal: 5N-Bicalutamide AA560 Antarlides Arabilin Apalutamide Atraric acid AZD-3514 Bakuchiol Bavdegalutamide BAY-1024767 Bicalutamide Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) BMS-501949 BMS-570511 BMS-641988 CH5137291 Cimetidine Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide Inocoterone Inocoterone acetate Ketoconazole Ketodarolutamide Lavender oil LG-105 LG-120907 LGD-1331 Linuron Masofaniten Methiocarb N-Butylbenzenesulfonamide N-Desmethylapalutamide N-Desmethylenzalutamide Nilutamide ONC1-13B Pentomone PF-998425 Phenothrin Prochloraz Procymidone Proxalutamide Pyrilutamide Ralaniten (EPI-002) Ralaniten acetate (EPI-506) RD-162 Rezvilutamide Ro 2-7239 Ro 5-2537 RU-22930 RU-56187 RU-57073 RU-58642 RU-58841 Seviteronel Thalidomide Topilutamide (fluridil) Valproic acid Vinclozolin YM-580 YM-92088 YM-175735 GPRC6AAgonists Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone See also Receptor/signaling modulators Androgens and antiandrogens Estrogen receptor modulators Progesterone receptor modulators List of androgens and anabolic steroids This article about a steroid is a stub. You can help Wikipedia by adding missing information.vte This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by adding missing information.vte
