Iguratimod

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;
CompTox Dashboard (EPA)	DTXSID0048971 ;
ECHA InfoCard	100.236.037
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.[1] 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.[1]

Adverse effects include Elevated transaminases, nausea, vomiting, stomach pain; rashes, and itchiness.[1]

It is a derivative of 7-methanesulfonylamino-6-phenoxychromones and is a chromone with two amide groups; it was first published in 2000.[1][2] It was submitted for regulatory approval in Japan in 2003; the application was withdrawn in 2009, and it was resubmitted with additional data in 2011 and approved for marketing in Japan in 2012.[1] Eisai and Toyama Chemical market it in Japan.[3] Approval was obtained in China in 2011 by Simcere, independently of the Japanese originators.[1][4]

During discovery and development it was called T-614 and it is marketed under the names Careram and Kolbet.[5]

References

Tanaka K, Yamaguchi T, Hara M (May 2015). "Iguratimod for the treatment of rheumatoid arthritis in Japan". Expert Review of Clinical Immunology. 11 (5): 565–73. doi:10.1586/1744666X.2015.1027151. PMID 25797025. S2CID 25134255.
Inaba T, Tanaka K, Takeno R, Nagaki H, Yoshida C, Takano S (January 2000). "Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6-phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models". Chemical & Pharmaceutical Bulletin. 48 (1): 131–9. doi:10.1248/cpb.48.131. PMID 10705489.
Bronson J, Dhar M, Ewing W, Lonberg N (2012). "Chapter Thirty-One – To Market, To Market—2011". Annual Reports in Medicinal Chemistry. 47: 499–569. doi:10.1016/B978-0-12-396492-2.00031-X.
"Iguratimod - Simcere". AdisInsight. Retrieved 27 May 2018.
"Iguratimod - Toyama Chemical". AdisInsight. Retrieved 27 May 2018.

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[Tanaka2015-1] Tanaka K, Yamaguchi T, Hara M (May 2015). "Iguratimod for the treatment of rheumatoid arthritis in Japan". Expert Review of Clinical Immunology. 11 (5): 565–73. doi:10.1586/1744666X.2015.1027151. PMID 25797025. S2CID 25134255.

[2] Inaba T, Tanaka K, Takeno R, Nagaki H, Yoshida C, Takano S (January 2000). "Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6-phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models". Chemical & Pharmaceutical Bulletin. 48 (1): 131–9. doi:10.1248/cpb.48.131. PMID 10705489.

[3] Bronson J, Dhar M, Ewing W, Lonberg N (2012). "Chapter Thirty-One – To Market, To Market—2011". Annual Reports in Medicinal Chemistry. 47: 499–569. doi:10.1016/B978-0-12-396492-2.00031-X.

[4] "Iguratimod - Simcere". AdisInsight. Retrieved 27 May 2018.

[5] "Iguratimod - Toyama Chemical". AdisInsight. Retrieved 27 May 2018.