Discovery of Soticlestat, a Potent and Selective Inhibitor for Cholesterol 24-Hydroxylase (CH24H)

J Med Chem. 2021 Aug 26;64(16):12228-12244. doi: 10.1021/acs.jmedchem.1c00864. Epub 2021 Aug 13.

Abstract

Cholesterol 24-hydroxylase (CH24H, CYP46A1), a brain-specific cytochrome P450 (CYP) family enzyme, plays a role in the homeostasis of brain cholesterol by converting cholesterol to 24S-hydroxycholesterol (24HC). Despite a wide range of potential of CH24H as a drug target, no potent and selective inhibitors have been identified. Here, we report on the structure-based drug design (SBDD) of novel 4-arylpyridine derivatives based on the X-ray co-crystal structure of hit derivative 1b. Optimization of 4-arylpyridine derivatives led us to identify 3v ((4-benzyl-4-hydroxypiperidin-1-yl)(2,4'-bipyridin-3-yl)methanone, IC50 = 7.4 nM) as a highly potent, selective, and brain-penetrant CH24H inhibitor. Following oral administration to mice, 3v resulted in a dose-dependent reduction of 24HC levels in the brain (1, 3, and 10 mg/kg). Compound 3v (soticlestat, also known as TAK-935) is currently under clinical investigation for the treatment of Dravet syndrome and Lennox-Gastaut syndrome as a novel drug class for epilepsies.

Publication types

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

MeSH terms

  • Animals
  • Brain / drug effects
  • Brain / enzymology
  • Cholesterol 24-Hydroxylase / antagonists & inhibitors*
  • Cholesterol 24-Hydroxylase / metabolism
  • Crystallography, X-Ray
  • Drug Stability
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology*
  • Female
  • Humans
  • Mice
  • Mice, Inbred C57BL
  • Microsomes, Liver / metabolism
  • Molecular Structure
  • Piperidines / chemical synthesis
  • Piperidines / metabolism
  • Piperidines / pharmacology*
  • Protein Binding
  • Pyridines / chemical synthesis
  • Pyridines / metabolism
  • Pyridines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Piperidines
  • Pyridines
  • soticlestat
  • Cholesterol 24-Hydroxylase