Iguratimod

Base Information

• Chemical Name: Iguratimod
• CAS No.: 123663-49-0
• Molecular Formula: C17H14N2O6S
• Molecular Weight: 374.374
• Hs Code.: 2935009090
• European Community (EC) Number: 808-127-0
• UNII: 4IHY34Y2NV
• DSSTox Substance ID: DTXSID0048971
• Nikkaji Number: J442.708D
• Wikipedia: Iguratimod
• Wikidata: Q13575264
• NCI Thesaurus Code: C65886
• Metabolomics Workbench ID: 153260
• ChEMBL ID: CHEMBL2107455
• Mol file: 123663-49-0.mol

Synonyms:3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one;T 614;T-614

Chemical Property of Iguratimod

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.8E-13mmHg at 25°C
• Melting Point: 238.0 to 242.0 °C
• Refractive Index: 1.673
• Boiling Point: 580.6 °C at 760 mmHg
• PKA: 5.58±0.20(Predicted)
• Flash Point: 304.9 °C
• PSA: 123.09000
• Density: 1.52 g/cm³
• LogP: 4.38780
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 374.05725734
• Heavy Atom Count: 26
• Complexity: 665

Purity/Quality:

99%min ^*data from raw suppliers

Iguratimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)NC1=C(C=C2C(=C1)OC=C(C2=O)NC=O)OC3=CC=CC=C3
• Recent ClinicalTrials: The Clinical Efficacy of Immunomodulators in RA Patients
• Recent NIPH Clinical Trials: Effect of tapering methotrexate in rheumatoid arthritis patients after add-on iguratimod therapy.
• Description: In August 2011, China’s State FDA approved Simcere Pharmaceutical Group’s new drug application for iguratimod (T-614), a disease modifying anti-rheumatic drug (DMARD) for the treatment of rheumatoid arthritis (RA). Preclinical in vivo studies indicated that iguratimod was effective in an established adjuvant-induced arthritis model (ED40=3.6 mg/kg) in rats and also efficacious in a type II collagen-induced arthritis model in DBA/1J mice at 30 mg and 100 mg/kg.
• Uses: Iguratimod acts as an anti-inflammatory agent, used primarily in the treatment of rheumatoid arthritis.
• Clinical Use: Iguratimod, which was discovered by Toyama Pharmaceuticals and jointly co-developed with Eisai in Japan, was approved by the PMDA (Pharmaceuticals and Medical Devices Agency) of Japan on June 29, 2012 for the treatment of rheumatoid arthritis. This drug was also independently developed by Simcere Pharmaceutical Group and is marked as Iremod? in China. The drug exhibited inhibitory effects on granuloma inflammation, and was shown to be efficacious for the prevention of joint destruction in adjuvant arthritis.

Technology Process of Iguratimod

There total 17 articles about Iguratimod 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: 87.0%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + α-formamido-2'-hydroxy-4'-methanesulfonamido-5'-phenoxyacetophenone (149457-03-4) → Iguratimod (123663-49-0)

Guidance literature:

In N,N-dimethyl-formamide; at 15 ℃; for 8h;

DOI:10.1248/cpb.48.131

Reference yield: 73.0%

N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide (123663-48-9) → Iguratimod (123663-49-0)

Guidance literature:

With formic acid; acetic anhydride; In dichloromethane; di-isopropyl ether;

Reference yield: 73.0%

formyl acetic anhydride (2258-42-6) + N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide (123663-48-9) → Iguratimod (123663-49-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 1h;

DOI:10.1248/cpb.48.131

upstream raw materials:

N,N-dimethyl-formamide dimethyl acetal

α-formamido-2'-hydroxy-4'-methanesulfonamido-5'-phenoxyacetophenone

formyl acetic anhydride

N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide

Downstream raw materials:

N-[3-(formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide monohydrate

Refernces

• 1、 -. "Method for the treatment and prevention of cachexia". . . Retrieved 2008/06/13.
• 2、 Inaba, Takihiro,Tanaka, Keiichi,Takeno, Ryuko,Nagaki, Hideyoshi,Yoshida, Chosaku,Takano, Shuntaro. "Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6- phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models". . p. 131 - 139. Retrieved 2007/10/03.