Simeprevir

Simeprevir (TMC435; TMC435350) is an oral, potent and highly specific hepatitis C virus (HCV) NS3/4A protease inhibitor with a Ki of 0.36 nM. Simeprevir inhibits HCV replication with an EC50 of 7.8 nM. Simeprevir also potently suppresses SARS-CoV-2 replication and synergizes with Remdesivir. Simeprevir inhibits the main protease (Mpro) and the RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2, and also modulates host immune responses[1][4].

Product Specifications

CAS Number

[923604-59-5]

Product Name Alternative

TMC435; TMC435350

UNSPSC

12352005

Hazard Statement

H315, H319, H320

Target

DNA/RNA Synthesis; HCV; HCV Protease; SARS-CoV

Type

Reference compound

Related Pathways

Anti-infection; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease

Applications

COVID-19-anti-virus

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/Simeprevir.html

Concentration

10mM

Purity

99.90

Solubility

DMSO : 14.29 mg/mL (ultrasonic)

Smiles

COC1=C(C)C2=C(C(O[C@H]3C[C@@H](C(N(C)CCCC/C=C\[C@H](C4)[C@]4(C(NS(=O)(C5CC5)=O)=O)N6)=O)[C@H](C6=O)C3)=CC(C7=NC(C(C)C)=CS7)=N2)C=C1

Molecular Formula

C38H47N5O7S2

Molecular Weight

749.94

Precautions

H315, H319, H320

References & Citations

[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 TI, et al. 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.|[3]Rajagopalan R, et al. Preclinical Characterization and Human Microdose Pharmacokinetics of ITMN-8187, a Nonmacrocyclic Inhibitor of the Hepatitis C Virus NS3 Protease. Antimicrob Agents Chemother. 2016 Dec 27;61 (1) . pii: e01569-16.|[4]Lo HS, et al. Simeprevir Potently Suppresses SARS-CoV-2 Replication and Synergizes with Remdesivir. ACS Cent Sci. 2021 May 26;7 (5) :792-802.