Cimicoxib

Base Information

• Chemical Name: Cimicoxib
• CAS No.: 265114-23-6
• Molecular Formula: C16H13 Cl F N3 O3 S
• Molecular Weight: 381.815
• European Community (EC) Number: 642-922-1
• UNII: W7FHJ107MC
• DSSTox Substance ID: DTXSID30181093
• Wikipedia: Cimicoxib
• Wikidata: Q5120133
• NCI Thesaurus Code: C77551
• Pharos Ligand ID: TUZ86U8CQYTP
• Metabolomics Workbench ID: 149391
• ChEMBL ID: CHEMBL435381
• Mol file: 265114-23-6.mol

Synonyms:cimicoxib

Chemical Property of Cimicoxib

Chemical Property:

• Vapor Pressure: 4.91E-14mmHg at 25°C
• Melting Point: 211-212 °C
• Boiling Point: 593.1°C at 760 mmHg
• PKA: 9.78±0.10(Predicted)
• Flash Point: 312.5°C
• PSA: 95.59000
• Density: 1.49g/cm³
• LogP: 4.76890
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 381.0350183
• Heavy Atom Count: 25
• Complexity: 553

Purity/Quality:

>98% ^*data from raw suppliers

Cimicoxib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=C(N=CN2C3=CC=C(C=C3)S(=O)(=O)N)Cl)F
• Recent ClinicalTrials: Cimicoxib for the Treatment of Major Depression (SECIM)
• Recent EU Clinical Trials: SAFETY AND EFFICACY OF CIMICOXIB, A SELECTIVE COX-2 INHIBITOR, IN COMBINATION WITH SERTRALINE COMPARED TO SERTRALINE COMBINED WITH PLACEBO IN TREATMENT OF MAJOR DEPRESSION
• Description: Cimicoxib is a non-steroidal anti-inflammatory drug (NSAID) that inhibits COX-2 selectively over COX-1 (IC50s = 0.005 and 3.3 μM, respectively). It inhibits paw swelling by 93% in a rat model of adjuvant-induced arthritis when administered at a dose of 1 mg/kg. Cimicoxib (3 mg/kg, p.o.) inhibits carrageenan-induced decreases in paw withdrawal latency in the hot plate test in a rat model of hyperalgesia. Formulations containing cimicoxib have been used in the treatment of pain and inflammation associated with osteoarthritis or surgery in dogs.
• Uses: Cimicoxib is a long-acting COX-2 Inhibitor and is developed as a non-steroidal anti-inflammatory veterinary drug used to treat dogs with inflammation and pain associated with osteoarthritis.

Technology Process of Cimicoxib

There total 7 articles about Cimicoxib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

1-(tert-butylaminosulfonylphenyl)-4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazole (499777-85-4) → cimicoxib (265114-23-6)

Guidance literature:

1-(tert-butylaminosulfonylphenyl)-4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazole; With hydrogenchloride; In water; for 3h; Acidic aqueous solution; Heating / reflux;

With sodium hydroxide; In water; pH=6;

Reference yield:

4-amino-N-(dimethylethyl)benzenesulfonamide (209917-48-6) → cimicoxib (265114-23-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / toluene / 24 h / 110 °C

2: 87 percent / K₂CO₃ / methanol; 1,2-dimethoxy-ethane / 3 h / Heating

3: 82 percent / N-chlorosuccinimide / acetonitrile / 24 h / 81 °C

4: 84 percent / aq. HCl / 3 h / Heating

With hydrogenchloride; N-chloro-succinimide; potassium carbonate; In methanol; 1,2-dimethoxyethane; toluene; acetonitrile;

DOI:10.1021/jm030765s

Reference yield:

p-acetylaminobenzenesulfonyl chloride (121-60-8) → cimicoxib (265114-23-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / 1,2-dimethoxy-ethane / 5 h / Heating

2: 89 percent / aq. KOH / methanol / 4 h / 100 °C

3: 100 percent / toluene / 24 h / 110 °C

4: 87 percent / K₂CO₃ / methanol; 1,2-dimethoxy-ethane / 3 h / Heating

5: 82 percent / N-chlorosuccinimide / acetonitrile / 24 h / 81 °C

6: 84 percent / aq. HCl / 3 h / Heating

With hydrogenchloride; potassium hydroxide; N-chloro-succinimide; potassium carbonate; In methanol; 1,2-dimethoxyethane; toluene; acetonitrile;

DOI:10.1021/jm030765s

upstream raw materials:

1-(tert-butylaminosulfonylphenyl)-4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazole

4-amino-N-(dimethylethyl)benzenesulfonamide

p-acetylaminobenzenesulfonyl chloride

N-(4-(N-(tert-butyl)sulfamoyl)phenyl)acetamide

Downstream raw materials:

diethyl N-[4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidate

N-[4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]phenylsulfonyl]phosphoramidatic acid

4-{4-chloro-5-[3-fluoro-4-(3-hydroxy-propoxy)-phenyl]-imidazol-1-yl}-benzenesulfonamide

4-{4-chloro-5-[3-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-imidazol-1-yl}-benzenesulfonamide

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