Synthesis physicochemical profile and PAMPA study of new NO-donor edaravone co-drugs

Bioorg Med Chem. 2012 Jan 15;20(2):841-50. doi: 10.1016/j.bmc.2011.11.065. Epub 2011 Dec 8.

Abstract

A new class of co-drugs were synthesised by joining antioxidant edaravone with a vasodilating substructure containing NO-donor nitrooxy functions, and characterised for their stability in different media, lipophilicity and permeability profile. The products display good stability in water/co-solvent at different pH. Conversely, they are rapidly metabolised into edaravone and NO-donor moieties when incubated in human serum or rat-liver homogenates. In the latter conditions time dependent production of nitrite/nitrate (NO(x)) occurs. The compounds display wide-ranging lipophilicity. PAMPA studies predict good gastrointestinal absorption for a number of these compounds. The title products are potentially useful for treating ROS-related conditions accompanied by decreased NO availability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antipyrine / analogs & derivatives*
  • Antipyrine / chemical synthesis
  • Antipyrine / chemistry
  • Antipyrine / pharmacokinetics
  • Drug Stability
  • Edaravone
  • Humans
  • Nitrates / metabolism
  • Nitric Oxide Donors / chemical synthesis
  • Nitric Oxide Donors / chemistry
  • Nitric Oxide Donors / pharmacokinetics
  • Nitrites / metabolism
  • Permeability
  • Rats
  • Vasodilator Agents / chemical synthesis*
  • Vasodilator Agents / chemistry
  • Vasodilator Agents / pharmacokinetics

Substances

  • Nitrates
  • Nitric Oxide Donors
  • Nitrites
  • Vasodilator Agents
  • Edaravone
  • Antipyrine