TFM-4AS-1

TFM-4AS-1
Clinical data
Other names	N-[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	188589-61-9;
PubChem CID	90488882;
ChemSpider	26232144;
Chemical and physical data
Formula	C27H33F3N2O2
Molar mass	474.568 g·mol−1
3D 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/s1; Key: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 (E_max = 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]

References

^ ^a ^b ^c 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.
^ ^a ^b ^c ^d ^e 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.
^ ^a ^b 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.

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