{{short description|Chemical compound with medical applications}} {{Drugbox | drug_name = | IUPAC_name = ''N''-(3-Formamido-4-oxo-6-phenoxy-4''H''-chromen-7-yl)methanesulfonamide | image = Iguratimod.svg | image_class = skin-invert-image | alt = | caption =
<!-- Clinical data --> | tradename = Careram; Kolbet | Drugs.com = | MedlinePlus = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category= | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number = 123663-49-0 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4IHY34Y2NV | ATCvet = | ATC_prefix = None | ATC_suffix = | DrugBank = | PubChem = 124246 | ChemSpiderID = 110694 | ChEMBL = 2107455 | synonyms = T-614
<!-- Chemical data --> | C=17 | H=14 | N=2 | O=6 | S=1 | smiles = O=S(=O)(Nc3c(Oc1ccccc1)cc2c(O/C=C(\C2=O)NC=O)c3)C | StdInChI = 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) | StdInChIKey = 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.<ref name=Tanaka2015>{{cite journal | vauthors = Tanaka K, Yamaguchi T, Hara M | s2cid = 25134255 | title = Iguratimod for the treatment of rheumatoid arthritis in Japan | journal = Expert Review of Clinical Immunology | volume = 11 | issue = 5 | pages = 565–73 | date = May 2015 | pmid = 25797025 | doi = 10.1586/1744666X.2015.1027151 }}</ref> 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.<ref name=Tanaka2015/>
Adverse effects include elevated transaminases, nausea, vomiting, stomach pain, rashes, and itchiness.<ref name=Tanaka2015/>
It is a derivative of 7-methanesulfonylamino-6-phenoxychromone and is a chromone with two amide groups; it was first reported in 2000.<ref name=Tanaka2015/><ref>{{cite journal | vauthors = Inaba T, Tanaka K, Takeno R, Nagaki H, Yoshida C, Takano S | title = Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6-phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models | journal = Chemical & Pharmaceutical Bulletin | volume = 48 | issue = 1 | pages = 131–9 | date = January 2000 | pmid = 10705489 | doi = 10.1248/cpb.48.131 | url = https://www.jstage.jst.go.jp/article/cpb1958/48/1/48_1_131/_pdf/-char/en | doi-access = free }}</ref> 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.<ref name=Tanaka2015/> Eisai and Toyama Chemical market it in Japan.<ref>{{cite journal| vauthors = Bronson J, Dhar M, Ewing W, Lonberg N |title=Chapter Thirty-One – To Market, To Market—2011|journal=Annual Reports in Medicinal Chemistry|date=2012|volume=47|pages=499–569|doi=10.1016/B978-0-12-396492-2.00031-X}}</ref> Approval was obtained in China in 2011 by Simcere, independently of the Japanese originators.<ref name=Tanaka2015/><ref>{{cite web|title=Iguratimod - Simcere|url=https://adisinsight.springer.com/drugs/800032226|publisher=AdisInsight|access-date=27 May 2018|language=en}}</ref>
During discovery and development it was called T-614 and it is marketed under the names Careram and Kolbet.<ref>{{cite web|title=Iguratimod - Toyama Chemical|url=https://adisinsight.springer.com/drugs/800001541|publisher=AdisInsight|access-date=27 May 2018|language=en}}</ref>
==References== {{reflist}}
Category:Anti-inflammatory and antirheumatic products Category:Chromones Category:Formamides Category:N-phenylmethanesulfonamide derivatives Category:Small-molecule drugs Category:Drugs with unknown mechanisms of action