Cimicoxib

NSAID analgesic veterinary medication

Cimicoxib
Names

Preferred IUPAC name 4-[4-Chloro-5-(3-fluoro-4-methoxyphenyl)-1H-imidazol-1-yl]benzene-1-sulfonamide
Identifiers
CAS Number	265114-23-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76127
ChEMBL	ChEMBL435381
ChemSpider	184745
ECHA InfoCard	100.170.774
PubChem CID	213053
UNII	W7FHJ107MC^Y
CompTox Dashboard (EPA)	DTXSID30181093
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⁻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

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

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

^ "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.

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)

Alminoprofen
Benoxaprofen^†
Carprofen^‡
Dexibuprofen
Dexketoprofen
Fenbufen
Fenoprofen
Flunoxaprofen
Flurbiprofen
Ibuprofen^#
Ibuproxam
Indoprofen^†
Ketoprofen
Loxoprofen
Miroprofen
Naproxen
Oxaprozin
Pelubiprofen
Piketoprofen
Pirprofen
Suprofen
Tarenflurbil
Tepoxalin^‡
Tiaprofenic acid
Vedaprofen^‡
Zaltoprofen
COX-inhibiting nitric oxide donator: Naproxcinod

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.