Discovery of AZD4625, a Covalent Allosteric Inhibitor of the Mutant GTPase KRASG12C

J Med Chem. 2022 May 12;65(9):6940-6952. doi: 10.1021/acs.jmedchem.2c00369. Epub 2022 Apr 26.

Abstract

KRAS is an archetypal high-value intractable oncology drug target. The glycine to cysteine mutation at codon 12 represents an Achilles heel that has now rendered this important GTPase druggable. Herein, we report our structure-based drug design approach that led to the identification of 21, AZD4625, a clinical development candidate for the treatment of KRASG12C positive tumors. Highlights include a quinazoline tethering strategy to lock out a bio-relevant binding conformation and an optimization strategy focused on the reduction of extrahepatic clearance mechanisms seen in preclinical species. Crystallographic analysis was also key in helping to rationalize unusual structure-activity relationship in terms of ring size and enantio-preference. AZD4625 is a highly potent and selective inhibitor of KRASG12C with an anticipated low clearance and high oral bioavailability profile in humans.

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Drug Design
  • Humans
  • Lung Neoplasms* / drug therapy
  • Mutation
  • Proto-Oncogene Proteins p21(ras) / genetics
  • Quinazolines / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • KRAS protein, human
  • Quinazolines
  • Proto-Oncogene Proteins p21(ras)