265114-23-6

Basic information

• Product Name: 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide
• Synonyms: 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide;Cimicoxib;4-(4-chloro-5-(3-fluoro-4-Methoxyphenyl)-1H-iMidazol-1-yl)benzene sulfonaMide
• CAS NO: 265114-23-6
• Molecular Formula: C₁₆H₁₃ClFN₃O₃S
• Molecular Weight: 381.81
• Mol File: 265114-23-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 211-212 °C
• Boiling Point: 593.1°C at 760 mmHg
• Flash Point: 312.5°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 4.91E-14mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 9.78±0.10(Predicted)
• CAS DataBase Reference: 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide(265114-23-6)
• EPA Substance Registry System: 4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide(265114-23-6)

Safety Data

• Hazardous Substances Data: 265114-23-6(Hazardous Substances Data)

Usage

Description

4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide is an imidazole derivative with substitutions at positions 1, 4, and 5 by 4-aminosulfonylphenyl, chloro, and 3-fluoro-4-methoxyphenyl groups, respectively. It is a selective cyclooxygenase 2 (COX-2) inhibitor, which makes it a valuable compound in the field of veterinary medicine.

Uses

Used in Veterinary Medicine:
4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide is used as a long-acting COX-2 inhibitor for the control of pain and inflammation associated with osteoarthritis in dogs. Its selective inhibition of COX-2 over COX-1 helps to reduce inflammation and pain without causing excessive side effects commonly associated with non-selective NSAIDs.
Used in Non-Steroidal Anti-Inflammatory Drug (NSAID) Formulations:
4-[4-chloro-5-(3-fluoro-4-methoxy-phenyl)imidazol-1-yl]benzenesulfonam ide is utilized in the development of NSAID formulations specifically designed for veterinary use. Its selective COX-2 inhibition property allows for effective treatment of pain and inflammation in dogs, with a reduced risk of gastrointestinal and renal side effects that may be associated with non-selective NSAIDs.

InChI: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)

Upstream product

• 499777-85-4 1-(tert-butylaminosulfonylphenyl)-4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazole 
• 499777-84-3 1-(tert-butylaminosulfonylphenyl)-5-(3-fluoro-4-methoxyphenyl)imidazole 
• 294885-56-6 N-(4-(N-(tert-butyl)sulfamoyl)phenyl)acetamide 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 209917-48-6 4-amino-N-(dimethylethyl)benzenesulfonamide 

Downstream Products

• 721445-64-3 N-[4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidatic acid 
• 935532-44-8 4-{4-chloro-5-[3-fluoro-4-(3-hydroxy-propoxy)-phenyl]-imidazol-1-yl}-benzenesulfonamide 
• 935532-43-7 4-{4-chloro-5-[3-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-imidazol-1-yl}-benzenesulfonamide 
• 927181-51-9 4-[4-chloro-5-(3-fluoro-4-hydroxyphenyl)-1H-imidazol-1-yl]benzenesulfonamide 
• 721445-74-5 dimethyl N-[4-[4-chloro-5-(3-fluoro-5-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidate 
• 721445-59-6 diethyl N-[4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidate 

Relevant articles and documents

CO-CRYSTALS OF TRAMADOL AND COXIBS

The present invention relates to co-crystals of tramadol and co-crystal formers selected from NSAIDs/coxibs, processes for preparation of the same and their uses in pharmaceutical formulations for the treatment of pain.

Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-Diarylimidazoles

The synthesis and the pharmacological activity of a series of 1,5-diarylimidazoles developed as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema, air-pouch, and hyperalgesia tests). Modification of all the positions of two regioisomeric imidazole cores led to the identification of 4-[4-chloro-5-(3-fluoro4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide (UR-8880, 51f) as the best candidate, which is now undergoing Phase I clinical trials.