Simeprevir

• CAT Number: I005499
• CAS Number: 923604-59-5
• Molecular Formula: C₃₈H₄₇N₅O₇S₂
• Molecular Weight: 749.96
• Purity: ≥95%
• Synonyms: TMC-435350;TMC 435350
• Target: Metabolic Enzyme/Protease
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• IC50: 0.36 nM(Ki); 7.8 nM (EC50)
• IUPAC Name: (1R,4R,6S,7Z,15R,17R)-N-cyclopropylsulfonyl-17-[7-methoxy-8-methyl-2-(4-propan-2-yl-1,3-thiazol-2-yl)quinolin-4-yl]oxy-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide
• InChI: InChI=1S/C38H47N5O7S2/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H,41,44)(H,42,46)/b10-8-/t23-,24-,27-,28-,38-/m1/s1
• InChIKey: JTZZSQYMACOLNN-VDWJNHBNSA-N
• SMILES: CC1=C(C=CC2=C1N=C(C=C2O[C@@H]3C[C@@H]4[C@@H](C3)C(=O)N(CCCC/C=C\[C@@H]5C[C@]5(NC4=O)C(=O)NS(=O)(=O)C6CC6)C)C7=NC(=CS7)C(C)C)OC

Simeprevir（Cat No.:I005499）is a direct-acting antiviral agent used in the treatment of chronic hepatitis C virus (HCV) infection. It is a second-generation NS3/4A protease inhibitor, targeting the viral protease essential for HCV replication. Simeprevir is effective against HCV genotype 1 and is typically used in combination with other antivirals to enhance efficacy and reduce resistance. Its once-daily oral administration, favorable safety profile, and high antiviral potency make it a key component of HCV combination therapies. Simeprevir significantly improves sustained virologic response rates, aiding in the management and potential eradication of HCV.

Reference

[1]. Raboisson P, et al. Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett. 2008 Sep 1;18(17):4853-8.


[2]. Lin, Tse-I.; Lenz, Oliver; Fanning, Gregory; Verbinnen, Thierry; Delouvroy, Frederic; In vitro activity and preclinical profile of TMC435350, a potent hepatitis C virus protease inhibitor. Antimicrobial Agents and Chemotherapy (2009), 53(4), 1377-1385. 


[3]. Xue W, Pan D, Yang Y, Liu H, Yao X.Molecular modeling study on the resistance mechanism of HCV NS3/4A serine protease mutants R155K, A156V and D168A to TMC435.Antiviral Res. 2012 Jan;93(1):126-37. Epub 2011 Nov 22. 


[4]. Manns M, Reesink H, Berg T, Dusheiko G, Flisiak R, Marcellin P, Moreno C, Lenz O, Meyvisch P, Peeters M, Sekar V, Simmen K, Verloes R.Rapid viral response of once-daily TMC435 plus pegylated interferon/ribavirin in hepatitis C genotype-1 patients: a randomized trial.Antivir Ther. 2011;16(7):1021-33. 


[5]. Lin TI, Lenz O, Fanning G, Verbinnen T, Delouvroy F, Scholliers A, Vermeiren K, Rosenquist A, Edlund M, Samuelsson B, Vrang L, de Kock H, Wigerinck P, Raboisson P, Simmen K.In vitro activity and preclinical profile of TMC435350, a potent hepatitis C virus protease inhibitor.Antimicrob Agents Chemother. 2009 Apr;53(4):1377-85. Epub 2009 Jan 26.