Cimicoxib
NSAID analgesic veterinary medication
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| Preferred IUPAC name
4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzene-1-sulfonamide | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.170.774 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C16H13ClFN3O3S | |
| Molar mass | 381.81 g·mol−1 |
| Pharmacology | |
| QM01AH93 (WHO) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
The chemical synthesis of Cimicoxib was reported:[2]
The reaction of N-acetylsulfanilyl chloride [121-60-8] (1) (available from chlorosulfonation of acetanilide) with tert-butylamine, gives N-(4-tert-butylsulfamoyl-phenyl)-acetamide [294885-56-6] (2). The acetyl group on nitrogen is then removed by heating with strong base to give N-tert-butyl 4-aminophenylsulfonamide [209917-48-6] (3). Condensation with 3-fluoro-4-anisaldehyde [351-54-2] (4) gives the anil, i.e. PC11132250 (5), which incorporates the two adjacent aromatic rings characteristic of COX-2 inhibitors. Reaction of the imine with TosMIC [36635-61-7] 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, PC11784436 (6). This ring is then halogenated with N-chlorosuccinimide (NCS) giving PC10274815 (7). Acid hydrolysis of the protecting group gives the free sulfonamide and thus cimicoxib (8).
