Discovery of the pan-genotypic hepatitis C virus NS3/4A protease inhibitor voxilaprevir (GS-9857): A component of Vosevi®

Bioorg Med Chem Lett. 2019 Aug 15;29(16):2428-2436. doi: 10.1016/j.bmcl.2019.03.037. Epub 2019 Mar 26.

Abstract

Treatment of hepatitis C virus (HCV) infection has been historically challenging due the high viral genetic complexity wherein there are eight distinct genotypes and at least 86 viral subtypes. While HCV NS3/4A protease inhibitors are an established treatment option for genotype 1 infection, limited coverage of genotypes 2 and/or 3 combined with serum alanine transaminase (ALT) elevations for some compounds has limited the broad utility of this therapeutic class. Our discovery efforts were focused on identifying an NS3/4A protease inhibitor with pan-genotypic antiviral activity, improved coverage of resistance associated substitutions, and a decreased risk of hepatotoxicity. Towards this goal, distinct interactions with the conserved catalytic triad of the NS3/4A protease were identified that improved genotype 3 antiviral activity. We further discovered that protein adduct formation strongly correlated with clinical ALT elevation for this therapeutic class. Improving metabolic stability and decreasing protein adduct formation through structural modifications ultimately resulted in voxilaprevir. Voxilaprevir, in combination with sofosbuvir and velpatasvir, has demonstrated pan-genotypic antiviral clinical activity. Furthermore, hepatotoxicity was not observed in Phase 3 clinical trials with voxilaprevir, consistent with our design strategy. Vosevi® (sofosbuvir, velpatasvir, and voxilaprevir) is now an approved pan-genotypic treatment option for the most difficult-to-cure individuals who have previously failed direct acting antiviral therapy.

Keywords: GS-9857; HCV; Hepatitis C virus; Protein adducts; VOX; Vosevi(®); Voxilaprevir.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aminoisobutyric Acids
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Carbamates / chemistry*
  • Cyclopropanes
  • Dose-Response Relationship, Drug
  • Drug Combinations
  • Drug Discovery*
  • Hepacivirus / drug effects*
  • Hepacivirus / genetics
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Humans
  • Lactams, Macrocyclic
  • Leucine / analogs & derivatives
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Proline / analogs & derivatives
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Quinoxalines
  • Sofosbuvir / chemistry*
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / genetics
  • Viral Nonstructural Proteins / metabolism

Substances

  • Aminoisobutyric Acids
  • Antiviral Agents
  • Carbamates
  • Cyclopropanes
  • Drug Combinations
  • Heterocyclic Compounds, 4 or More Rings
  • Lactams, Macrocyclic
  • Macrocyclic Compounds
  • NS3 protein, hepatitis C virus
  • NS4 protein, hepatitis C virus
  • Protease Inhibitors
  • Quinoxalines
  • Sulfonamides
  • Viral Nonstructural Proteins
  • sofosbuvir velpatasvir voxilaprevir drug combination
  • voxilaprevir
  • Proline
  • Leucine
  • Sofosbuvir