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	1114546-03-0;
PubChem CID	59556974;
Chemical and physical data
Formula	C14H13F3N2O2
Molar mass	298.265 g·mol−1
3D model (JSmol)	Interactive image;
	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]

References

^ US 8420694, Hasuoka A, "Pyrrolidin-2-one derivatives as androgen receptor modulator", issued 16 April 2013, assigned to Takeda Pharmaceutical Co Ltd.
^ 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.
^ 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.

[1] US 8420694, Hasuoka A, "Pyrrolidin-2-one derivatives as androgen receptor modulator", issued 16 April 2013, assigned to Takeda Pharmaceutical Co Ltd.

[pmid28454849-2] 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.

[pmid33672769-3] 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.

[1]

[2]

[3]

See also

References