Compound 2f (SARM) explained
| Iupac Name: | 4-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile |
| Legal Status: | Investigational |
| Cas Number: | 1114546-03-0 |
| Pubchem: | 59556974 |
| Stdinchi: | 1S/C14H13F3N2O2/c1-2-11-12(20)6-13(21)19(11)9-4-3-8(7-18)10(5-9)14(15,16)17/h3-5,11-12,20H,2,6H2,1H3/t11-,12-/m0/s1 |
| Stdinchikey: | LJQBTMVNFWIQQC-RYUDHWBXSA-N |
| Smiles: | CC[C@H]1[C@H](CC(=O)N1C2=CC(=C(C=C2)C#N)C(F)(F)F)O |
| C: | 14 |
| H: | 13 |
| F: | 3 |
| N: | 2 |
| O: | 2 |
Compound 2f (SARM) is a drug which acts as a selective androgen receptor modulator (SARM), originally developed by Takeda Pharmaceutical for the treatment of prostate cancer. It is a potent but tissue specific androgen agonist with an EC50 of 4.7nM, producing anabolic effects on muscles and in the central nervous system but with little effect on the prostate gland, and inducing sexual behaviour in animal studies.[1] [2] [3]
See also
Notes and References
- Pyrrolidin-2-one derivatives as androgen receptor modulator . Hasuoka A . Takeda Pharmaceutical Co Ltd. . US . 8420694 . 16 April 2013 .
- Aikawa K, Asano M, Ono K, Habuka N, Yano J, Wilson K, Fujita H, Kandori H, Hara T, Morimoto M, Santou T, Yamaoka M, Nakayama M, Hasuoka A . 6 . Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs) Part III: Discovery of 4-(5-oxopyrrolidine-1-yl)benzonitrile derivative 2f as a clinical candidate . Bioorganic & Medicinal Chemistry . 25 . 13 . 3330–3349 . July 2017 . 28454849 . 10.1016/j.bmc.2017.04.018 .
- Mohler ML, Sikdar A, Ponnusamy S, Hwang DJ, He Y, Miller DD, Narayanan R . An Overview of Next-Generation Androgen Receptor-Targeted Therapeutics in Development for the Treatment of Prostate Cancer . International Journal of Molecular Sciences . 22 . 4 . February 2021 . 2124 . 33672769 . 7924596 . 10.3390/ijms22042124 . free .
