Chemistry:Iguratimod

Short description: Chemical compound with medical applications

Iguratimod

Clinical data
Trade names	Careram; Kolbet
Other names	T-614
ATC code	None
Identifiers
IUPAC name N-(3-Formamido-4-oxo-6-phenoxy-4H-chromen-7-yl)methanesulfonamide
CAS Number	123663-49-0
PubChem CID	124246
ChemSpider	110694
UNII	4IHY34Y2NV
ChEMBL	ChEMBL2107455
Chemical and physical data
Formula	C17H14N2O6S
Molar mass	374.37 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=S(=O)(Nc3c(Oc1ccccc1)cc2c(O/C=C(\C2=O)NC=O)c3)C
InChI InChI=1S/C17H14N2O6S/c1-26(22,23)19-13-8-15-12(17(21)14(9-24-15)18-10-20)7-16(13)25-11-5-3-2-4-6-11/h2-10,19H,1H3,(H,18,20) Key:ANMATWQYLIFGOK-UHFFFAOYSA-N

Iguratimod is an anti-inflammatory small molecule drug used for the treatment of rheumatoid arthritis, together with methotrexate in Japan and China. As of 2015 the biological target was not known, but it prevents NF-κB activation and subsequently selectively inhibits COX-2 and several inflammatory cytokines.

Adverse effects include elevated transaminases, nausea, vomiting, stomach pain; rashes, and itchiness.

It is a derivative of 7-methanesulfonylamino-6-phenoxychromones and is a chromone with two amide groups; it was first published in 2000. It was submitted for regulatory approval in Japan in 2003; the application was withdrawn in 2009, and it was resubmitted with additional data in 2011 and approved for marketing in Japan in 2012. Eisai and Toyama Chemical market it in Japan. Approval was obtained in China in 2011 by Simcere, independently of the Japanese originators.

During discovery and development it was called T-614 and it is marketed under the names Careram and Kolbet.