Synthesis and anti-inflammatory activity of the major metabolites of imrecoxib

Bioorg Med Chem Lett. 2009 Apr 15;19(8):2270-2. doi: 10.1016/j.bmcl.2009.02.090. Epub 2009 Feb 27.

Abstract

We have developed a novel and moderately selective COX-2 inhibitor, imrecoxib, as a new anti-inflammatory drug. We describe herein the preparation of the major metabolites M2 and M4 of imrecoxib, as well as the in vitro and in vivo activities of the two compounds. The results showed that both M2 and M4 are potential COXs inhibitors with a moderate COX-1/COX-2 selectivity, and their anti-inflammatory activity in vivo was equal to or slightly higher than the clinical celecoxib.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / metabolism*
  • Anti-Inflammatory Agents, Non-Steroidal / therapeutic use
  • Celecoxib
  • Cyclooxygenase 2 Inhibitors / chemical synthesis
  • Cyclooxygenase 2 Inhibitors / metabolism
  • Cyclooxygenase 2 Inhibitors / therapeutic use
  • Dose-Response Relationship, Drug
  • Edema / drug therapy
  • Edema / metabolism
  • Humans
  • Mice
  • Pyrazoles / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / metabolism*
  • Pyrroles / therapeutic use
  • Rats
  • Sulfides / chemical synthesis*
  • Sulfides / metabolism*
  • Sulfides / therapeutic use
  • Sulfonamides / chemistry

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase 2 Inhibitors
  • Imrecoxib
  • Pyrazoles
  • Pyrroles
  • Sulfides
  • Sulfonamides
  • Celecoxib