TFM-4AS-1

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 addition, it does not promote growth of the prostate gland and it antagonizes the actions of dihydrotestosterone (DHT) in the seminal vesicles.[2] Structurally, TFM-4AS-1 is a 4-azasteroid.[1]

TFM-4AS-1
Clinical data
Other namesN-[2-(Trifluoromethyl)phenyl]-3-oxo-4-aza-4-methyl-5α-androst-1-en-17α-carboxamide
Identifiers
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 Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H33F3N2O2
Molar mass474.568 g·mol−1
3D model (JSmol)
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/s1
  • Key:YFBLEKKYWFJKBP-HRVOXWHZSA-N

See also

References
  1. 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.
  2. 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.
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