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1 Synthesis  





2 References  














Cimicoxib






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From Wikipedia, the free encyclopedia
 


Cimicoxib
Names
Preferred IUPAC name

4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]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=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

  • 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−1
Pharmacology

ATCvet code

QM01AH93 (WHO)

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 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.[1] It acts as a COX-2 inhibitor.

Synthesis[edit]

Cimicoxib synthesis:[2]

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[edit]

  1. ^ "European Public Assessment Report: Cimalgex (cimicoxib)". European Medicines Agency. 17 September 2018.
  • ^ 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.

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  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Cimicoxib&oldid=1182072998"

    Categories: 
    COX-2 inhibitors
    Nonsteroidal anti-inflammatory drugs
    Imidazoles
    Fluoroarenes
    Organochlorides
    Sulfonamides
    Veterinary medicine stubs
    Musculoskeletal system drug stubs
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    Articles without KEGG source
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    Chembox image size set
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    This page was last edited on 26 October 2023, at 23:48 (UTC).

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