Cimicoxib

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Cimicoxib
Cimicoxib.svg
Names
IUPAC name
4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide
Identifiers
265114-23-6
ATCvet code QM01AH93
ChEBI CHEBI:76127
ChEMBL ChEMBL435381
ChemSpider 184745
Jmol-3D images Image
PubChem 213053
Properties
C16H13ClFN3O3S
Molar mass 381.81 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cimicoxib (UR-8880 trade name Cimalgex) is a non-steroidal anti-inflammatory drug (NSAID) used in veterinary medicine to treat dogs for pain and inflammation associated with osteoarthritis and for the management of pain and inflammation associated with surgery.[1] It acts as a COX-2 inhibitor.

Synthesis[edit]

Cimicoxib synthesis:[2]

Reaction of the imine with tosylisocyanate in the presence of potassium carbonate leads to what may be viewed as 2+3 cycloaddition of the nitrogen analogue of a ketene to form the imidazole ring.

References[edit]

  1. ^ "European Public Assessment Report: Cimalgex (cimicoxib)". European Medicines Agency. 
  2. ^ Almansa, C.; Alfón, J.; De Arriba, A. F.; Cavalcanti, F. L.; Escamilla, I.; Gómez, L. A.; Miralles, A.; Soliva, R.; Bartrolí, J.; Carceller, E.; Merlos, M.; García-Rafanell, J. N. (2003). "Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors:  1,5-Diarylimidazoles". Journal of Medicinal Chemistry 46 (16): 3463. doi:10.1021/jm030765s.