Cimicoxib
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide
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| Identifiers | |
| ChEBI | CHEBI:76127 |
| ChEMBL | ChEMBL435381 |
| ChemSpider | 184745 |
| Jmol 3D model | Interactive image |
| PubChem | 213053 |
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| Properties | |
| C16H13ClFN3O3S | |
| Molar mass | 381.81 g·mol−1 |
| Pharmacology | |
| QM01AH93 (WHO) | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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 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]
- ^ "European Public Assessment Report: Cimalgex (cimicoxib)". European Medicines Agency.
- ^ 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.
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