| Identification | Back Directory | [Name]
Deracoxib | [CAS]
169590-41-4 | [Synonyms]
Sc 46
DeraM
Sc 59046
Deramaxx
Deracoxib
Deracoxib-d3
Unii-vx29jb5xwv
Deracoxib [usan]
4-[3-(difluoromethyl)-5-(3-fluoro-4-methoxyphenyl)pyrazol-1-yl]benzenesulfonamide
4-(3-(Difluoromethyl)-5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-1-yl)benzenesulfonamide
4-[5-(3-Fluoro-4-Methoxyphenyl)-3-(difluoroMethyl)-1H-pyrazol-1-yl]benzenesulfonaMide
Benzenesulfonamide, 4-3-(difluoromethyl)-5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-1-yl- | [EINECS(EC#)]
807-307-6 | [Molecular Formula]
C17H14F3N3O3S | [MDL Number]
MFCD09837763 | [MOL File]
169590-41-4.mol | [Molecular Weight]
397.37 |
| Chemical Properties | Back Directory | [Melting point ]
159-161° | [Boiling point ]
575.5±60.0 °C(Predicted) | [density ]
1.48 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Acetonitrile (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
9.69±0.10(Predicted) | [color ]
Light Brown | [InChI]
InChI=1S/C17H14F3N3O3S/c1-26-16-7-2-10(8-13(16)18)15-9-14(17(19)20)22-23(15)11-3-5-12(6-4-11)27(21,24)25/h2-9,17H,1H3,(H2,21,24,25) | [InChIKey]
WAZQAZKAZLXFMK-UHFFFAOYSA-N | [SMILES]
C1(S(N)(=O)=O)=CC=C(N2C(C3=CC=C(OC)C(F)=C3)=CC(C(F)F)=N2)C=C1 |
| Hazard Information | Back Directory | [Uses]
Deracoxib is a non-steroidal anti-inflammatory drug (NSAID) of the coxib class. Deracoxin is a selective cyclooxygenase-2 (COX-2) inhibitor used in the treatment of osteoarthritis in dogs. At low dose
s, adminsitartion of Deracoxin showed no factors associated with gastrointestinal tract perforation. | [Definition]
ChEBI: A member of the class of pyrazoles that is 1H-pyrazole which is substituted at positions 1, 3, and 5 by 4-sulfamoylphenyl, difluoromethyl and 3-fluoro-4-methoxyphenyl groups, respectively. A selective cyclooxygenase 2 inhibitor, it is us
d in veterinary medicine for the control of pain and inflammation associated with osteoarthritis in dogs. | [Biological Activity]
Deracoxib is an orally active cyclooxygenase-2 (COX-2) inhibitor with >48-fold selectivity over COX-1 (IC50 of 203-189 nM against COX-2-dependent PGE2 production vs. IC50 of 9.85-9.96 μM against COX-1-dependent TxB2 production in dog whole blood). Deracoxib is also reported to exhibit inhibitory activity against phosphodiesterase (Ki = 3.6 μM against human PDE4D3) as well as positive modulatory effiacy toward 2-APB-stimulated transient receptor potential vanilloid 3 channel (TRPV3) activity. | [Synthesis]
The general procedure for the synthesis of 4-(3-(difluoromethyl)-5-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-1-yl)benzenesulfonamide from 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)butane-1,3-dione and p-hydrazinylbenzenesulfonamide hydrochloride is as follows: 7.0 g (28.4 mmol) of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)butane-1,3-dione was dissolved in 150 mL of ethanol. methoxyphenyl)butane-1,3-dione was dissolved in 150 mL of ethanol followed by addition of 7.4 g (33 mmol) of p-hydrazinylbenzenesulfonamide hydrochloride. The reaction mixture was stirred under reflux conditions for 16 hours. After completion of the reaction, the reaction solution was allowed to cool to room temperature and water was added slowly until crystals precipitated. The precipitate was collected by filtration and washed with a suitable solvent and finally dried under vacuum to give a light yellow solid product in 87% yield. | [Veterinary Drugs and Treatments]
Deracoxib is indicated for the treatment of post-operative pain
(higher dose, 7 day maximum), and for the treatment of pain and
inflammation associated with osteoarthritis (lower dose, ongoing
dosing) in dogs.
Like piroxicam, deracoxib is of interest in adjunctive treatment
of transitional cell carcinoma of the bladder; investigations into this
use are ongoing. | [IC 50]
COX-2 | [storage]
Store at -20°C | [References]
[1] Patent: CN107686465, 2018, A. Location in patent: Paragraph 0043; 0065; 0066
[2] Patent: US6342510, 2002, B1. Location in patent: Page column 28 - 29
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 9, p. 1347 - 1365 |
|
|