Discovery, oral pharmacokinetics and in vivo efficacy of velusetrag, a highly selective 5-HT(4) receptor agonist that has achieved proof-of-concept in patients with chronic idiopathic constipation

Bioorg Med Chem Lett. 2012 Oct 1;22(19):6048-52. doi: 10.1016/j.bmcl.2012.08.051. Epub 2012 Aug 21.

Abstract

Utilization of Theravance's multivalent approach to drug discovery towards 5-HT(4) receptor agonists with a focus on identification of neutral (non-charged at physiological pH) secondary binding groups is described. Optimization of a quinolone-tropane primary binding group with a chiral 2-propanol linker to a range of neutral secondary binding group motifs, for binding affinity and functional potency at the 5-HT(4) receptor, selectivity over the 5-HT(3) receptor, oral pharmacokinetics, and in vivo efficacy in models of GI motility, afforded velusetrag (TD-5108). Velusetrag has achieved proof-of-concept in patients with chronic idiopathic constipation.

MeSH terms

  • Animals
  • Azabicyclo Compounds / administration & dosage
  • Azabicyclo Compounds / pharmacokinetics*
  • Azabicyclo Compounds / pharmacology*
  • Azabicyclo Compounds / therapeutic use
  • Chronic Disease
  • Constipation / drug therapy*
  • Drug Discovery*
  • Guinea Pigs
  • Humans
  • Molecular Structure
  • Rats
  • Receptors, Serotonin, 5-HT4 / metabolism*
  • Serotonin 5-HT4 Receptor Agonists / chemistry
  • Serotonin 5-HT4 Receptor Agonists / pharmacokinetics*
  • Serotonin 5-HT4 Receptor Agonists / pharmacology*
  • Serotonin 5-HT4 Receptor Agonists / therapeutic use
  • Structure-Activity Relationship

Substances

  • Azabicyclo Compounds
  • Serotonin 5-HT4 Receptor Agonists
  • TD-5108
  • Receptors, Serotonin, 5-HT4