Firocoxib

Base Information

• Chemical Name: Firocoxib
• CAS No.: 189954-96-9
• Molecular Formula: C₁₇H₂₀O₅S
• Molecular Weight: 336.409
• European Community (EC) Number: 837-109-5
• NSC Number: 758895
• UNII: Y6V2W4S4WT
• DSSTox Substance ID: DTXSID40870188
• Nikkaji Number: J1.153.112A
• Wikipedia: Firocoxib
• Wikidata: Q2034390
• NCI Thesaurus Code: C65686
• Pharos Ligand ID: SWA7XHDF39J4
• Metabolomics Workbench ID: 152251
• ChEMBL ID: CHEMBL69998
• Mol file: 189954-96-9.mol

Synonyms:3-(cyclopropylmethoxy)-4-(4-methylsulfonylphenyl)-5,5-dimethylfuranone;Equioxx;firocoxib;ML 1,785,713;ML 1785713;ML-1,785,713;ML-1785713;ML1,785,713;ML1785713

Chemical Property of Firocoxib

Chemical Property:

• Vapor Pressure: 9.72E-13mmHg at 25°C
• Melting Point: 78-80°C
• Refractive Index: 1.584
• Boiling Point: 563.9°Cat760mmHg
• Flash Point: 294.8°C
• PSA: 78.05000
• Density: 1.31
• LogP: 3.64400
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 336.10314491
• Heavy Atom Count: 23
• Complexity: 614

Purity/Quality:

99.5% ^*data from raw suppliers

Firocoxib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=C(C(=O)O1)OCC2CC2)C3=CC=C(C=C3)S(=O)(=O)C)C
• Description: Firocoxib is a selective inhibitor of COX-2 (IC50s = 0.13 and 7.5 μM for COX-2 and COX-1, respectively, in isolated cat blood). It inhibits LPS-induced production of prostaglandin E2 (PGE2; ) in isolated dog, horse, and cat whole blood ex vivo. Firocoxib decreases lameness, induces analgesia, and improves range of motion in dogs and horses with osteoarthritis when administered at doses of 5 and 0.1 mg/kg per day, respectively. Formulations containing firocoxib have been used in dogs and horses with osteoarthritis.
• Uses: antibacterial A selective cyclooxygenase-2-(COX-2) inhibitor. Anti-inflammatory; analgesic.

Technology Process of Firocoxib

There total 27 articles about Firocoxib 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: 94.6%

Cyclopropylmethanol (2516-33-8) + 3-hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-one (189955-89-3) → 3-(Cyclopropylmethoxy)-5.5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one (189954-96-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In dichloromethane; at -5 - 10 ℃; for 2h; Solvent;

Reference yield: 94.0%

2-cyclopropylmethoxyacetic acid [1,1-dimethyl-2-(4-methanesulfonylphenyl)-2-oxoethyl]ester (246869-15-8) → 3-(Cyclopropylmethoxy)-5.5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one (189954-96-9)

Guidance literature:

With isopropyl Trifluoroacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 12h; Reflux;

Reference yield: 89.0%

3-(cyclopropylmethoxy)-5,5-dimethyl-4-[4-(methylthio)phenyl]furan-2(5H)-one (256339-21-6) → 3-(Cyclopropylmethoxy)-5.5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one (189954-96-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02677

upstream raw materials:

2-cyclopropylmethoxyacetic acid [1,1-dimethyl-2-(4-methanesulfonylphenyl)-2-oxoethyl]ester

methyl-phenyl-thioether

2-methyl-1-(4-(methylthio)phenyl)-propan-1-one

2-hydroxy-2-methyl-1-(4-(methylthio)phenyl)-propan-1-one

Refernces

• 1、 -. "Preparation method of firocoxib". . . Retrieved 2019/10/01.
• 2、 -. "Preparation method of ferocoxib". . . Retrieved 2019/11/28.