Oral pharmacokinetics and efficacy of oral phospholipid remdesivir nucleoside prodrugs against SARS-CoV-2 in mice

Antimicrob Agents Chemother. 2024 Oct 8;68(10):e0103924. doi: 10.1128/aac.01039-24. Epub 2024 Sep 6.

Abstract

Oral broad-spectrum antivirals are urgently needed for the treatment of many emerging and contemporary RNA viruses. We previously synthesized 1-O-octadecyl-2-O-benzyl-sn-glyceryl-P-RVn (ODBG-P-RVn, V2043), a phospholipid prodrug of GS-441524 (remdesivir nucleoside, RVn), and demonstrated its in vivo efficacy in a SARS-CoV-2 mouse model. Structure-activity relationship studies focusing on the prodrug scaffold identified two modifications, 3-fluoro-4-methoxy-benzyl (V2053) and 4-cyano-benzyl (V2067), that significantly enhanced the in vitro broad-spectrum antiviral activity against multiple RNA viruses when compared to V2043. Here, we demonstrate that V2043, V2053, and V2067 are all orally bioavailable, well-tolerated, and achieve high sustained plasma levels after single oral daily dosing. All three phospholipid prodrugs are significantly more active than RVn in vitro and significantly reduce SARS-CoV-2 lung titers in prophylaxis and treatment mouse models of SARS-CoV-2 B.1.351 infection. On a molar basis, V2043 and V2067 are substantially more active than obeldesivir/GS-5245 and molnupiravir in vivo. Together, these data support the continued development of phospholipid RVn prodrugs for the treatment of SARS-CoV-2 and other RNA viruses of clinical concern.

Keywords: COVID-19; SARS-CoV-2; antiviral agent; broad spectrum antiviral; in vivo efficacy; lipid prodrug; mouse model; pharmacokinetics; remdesivir; remdesivir nucleoside.

MeSH terms

  • Adenosine / analogs & derivatives
  • Adenosine Monophosphate* / analogs & derivatives
  • Adenosine Monophosphate* / pharmacokinetics
  • Adenosine Monophosphate* / pharmacology
  • Administration, Oral
  • Alanine* / analogs & derivatives
  • Alanine* / pharmacokinetics
  • Alanine* / pharmacology
  • Animals
  • Antiviral Agents* / pharmacokinetics
  • Antiviral Agents* / pharmacology
  • COVID-19 / virology
  • COVID-19 Drug Treatment*
  • Chlorocebus aethiops
  • Disease Models, Animal
  • Female
  • Humans
  • Lung / drug effects
  • Lung / metabolism
  • Lung / virology
  • Mice
  • Phospholipids
  • Prodrugs* / pharmacokinetics
  • Prodrugs* / pharmacology
  • SARS-CoV-2* / drug effects
  • Structure-Activity Relationship
  • Vero Cells

Substances

  • Prodrugs
  • Antiviral Agents
  • remdesivir
  • Adenosine Monophosphate
  • Alanine
  • GS-441524
  • Phospholipids
  • Adenosine