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Cimicoxib

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NSAID analgesic veterinary medication
Cimicoxib
Names
Preferred IUPAC name 4-benzene-1-sulfonamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.170.774 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H13ClFN3O3S/c1-24-14-7-2-10(8-13(14)18)15-16(17)20-9-21(15)11-3-5-12(6-4-11)25(19,22)23/h2-9H,1H3,(H2,19,22,23)Key: KYXDNECMRLFQMZ-UHFFFAOYSA-N
  • InChI=1/C16H13ClFN3O3S/c1-24-14-7-2-10(8-13(14)18)15-16(17)20-9-21(15)11-3-5-12(6-4-11)25(19,22)23/h2-9H,1H3,(H2,19,22,23)Key: KYXDNECMRLFQMZ-UHFFFAOYAQ
SMILES
  • O=S(=O)(c3ccc(n1c(c(Cl)nc1)c2ccc(OC)c(F)c2)cc3)N
Properties
Chemical formula C16H13ClFN3O3S
Molar mass 381.81 g·mol
Pharmacology
ATCvet code QM01AH93 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cimicoxib (UR-8880 trade name Cimalgex) is a nonsteroidal 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. It acts as a COX-2 inhibitor.

Synthesis

Cimicoxib synthesis:

Reaction of the imine with TosMIC 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

  1. "European Public Assessment Report: Cimalgex (cimicoxib)". European Medicines Agency. 17 September 2018.
  2. Almansa, Carmen; Alfón, José; de Arriba, Alberto F.; Cavalcanti, Fernando L.; Escamilla, Ignasi; Gómez, Luis A.; Miralles, Agustí; Soliva, Robert; Bartrolí, Javier; Carceller, Elena; Merlos, Manuel; García-Rafanell, Julián (2003). "Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors:  1,5-Diarylimidazoles". Journal of Medicinal Chemistry. 46 (16): 3463–3475. doi:10.1021/jm030765s. ISSN 0022-2623. PMID 12877584.
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use.


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