Compound 2f (SARM)

Compound 2f (SARM)
Legal status
Legal status
  • Investigational
Identifiers
IUPAC name
  • 4-[(2S,3S)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile
CAS Number
PubChem CID
Chemical and physical data
FormulaC14H13F3N2O2
Molar mass298.265 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@H]1[C@H](CC(=O)N1C2=CC(=C(C=C2)C#N)C(F)(F)F)O
InChI
  • InChI=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
  • Key:LJQBTMVNFWIQQC-RYUDHWBXSA-N

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

References

  1. ↑ US 8420694, Hasuoka A, "Pyrrolidin-2-one derivatives as androgen receptor modulator", issued 16 April 2013, assigned to Takeda Pharmaceutical Co Ltd.
  2. ↑ Aikawa K, Asano M, Ono K, Habuka N, Yano J, Wilson K, et al. (July 2017). "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. doi:10.1016/j.bmc.2017.04.018. PMID 28454849.
  3. ↑ Mohler ML, Sikdar A, Ponnusamy S, Hwang DJ, He Y, Miller DD, Narayanan R (February 2021). "An Overview of Next-Generation Androgen Receptor-Targeted Therapeutics in Development for the Treatment of Prostate Cancer". International Journal of Molecular Sciences. 22 (4): 2124. doi:10.3390/ijms22042124. PMC 7924596. PMID 33672769.
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