Iguratimod

• CAT Number: I000946
• CAS Number: 123663-49-0
• Molecular Formula: C17H14N2O6S
• Molecular Weight: 374.37
• Purity: ≥95%
• Target: COX
• Solubility: 10 mM in DMSO
• Storage: Store at -20°C
• IUPAC Name: N-[7-(methanesulfonamido)-4-oxo-6-phenoxychromen-3-yl]formamide
• 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)
• InChIKey: ANMATWQYLIFGOK-UHFFFAOYSA-N
• SMILES: CS(=O)(=O)NC1=C(C=C2C(=C1)OC=C(C2=O)NC=O)OC3=CC=CC=C3

Iguratimod (CAt: I000946), also known as T-614, is an orally administered disease-modifying antirheumatic drug (DMARD). It exerts immunomodulatory and anti-inflammatory effects, making it useful in the treatment of rheumatoid arthritis (RA) and other autoimmune diseases. Iguratimod inhibits the production of pro-inflammatory cytokines, such as tumor necrosis factor-alpha (TNF-α), interleukin-1 (IL-1), and interleukin-6 (IL-6), which are involved in the pathogenesis of RA. It also modulates the activity of T cells and B cells, further contributing to its immunomodulatory properties. Iguratimod has demonstrated efficacy in reducing disease activity, improving symptoms, and slowing the progression of joint damage in RA patients.

Reference

1:Effects of iguratimod on the levels of circulating regulators of bone remodeling and bone remodeling markers in patients with rheumatoid arthritis. Wang X, Ma C, Li P, Zhao F, Bi L.Clin Rheumatol. 2017 May 4. doi: 10.1007/s10067-017-3668-8. [Epub ahead of print] PMID: 28474138
2:Safety and effectiveness of 24-week treatment with iguratimod, a new oral disease-modifying antirheumatic drug, for patients with rheumatoid arthritis: interim analysis of a post-marketing surveillance study of 2679 patients in Japan. Mimori T, Harigai M, Atsumi T, Fujii T, Kuwana M, Matsuno H, Momohara S, Takei S, Tamura N, Takasaki Y, Ikeuchi S, Kushimoto S, Koike T.Mod Rheumatol. 2016 Dec 21:1-11. doi: 10.1080/14397595.2016.1265695. [Epub ahead of print] PMID: 27919207
3:Effect of iguratimod and methotrexate on RANKL and OPG expression in serum and IL-1β-induced fibroblast-like synoviocytes from patients with rheumatoid arthritis. Wang XT, Li P, Xu TS, Ding R, Zhang X, Bi LQ.Cell Mol Biol (Noisy-le-grand). 2016 Oct 31;62(12):44-50. doi: 10.14715/cmb/2016.62.12.8. PMID: 27894399
4:Identification of Iguratimod as an Inhibitor of Macrophage Migration Inhibitory Factor (MIF) with Steroid-sparing Potential. Bloom J, Metz C, Nalawade S, Casabar J, Cheng KF, He M, Sherry B, Coleman T, Forsthuber T, Al-Abed Y.J Biol Chem. 2016 Dec 16;291(51):26502-26514. Epub 2016 Oct 28. PMID: 27793992
5:Anti-rheumatic drug iguratimod (T-614) alleviates cancer-induced bone destruction via down-regulating interleukin-6 production in a nuclear factor-κB-dependent manner. Sun Y, Ye DW, Zhang P, Wu YX, Wang BY, Peng G, Yu SY.J Huazhong Univ Sci Technolog Med Sci. 2016 Oct;36(5):691-699. Epub 2016 Oct 18. PMID: 27752889
6:Inhibitory Effect of Anti-rheumatic Drug Iguratimod for Hepatocellular Carcinogenesis by Inhibition of Serum Interleukin-8 Production. Sakamoto T, Ishii Y, Shiba H, Furukawa K, Fujiwara Y, Haruki K, Iwase R, Shirai Y, Yanaga K.Anticancer Res. 2016 Jul;36(7):3301-6. PMID: 27354586
7:[DMARDs (Focusing on iguratimod)]. Ito S.Nihon Rinsho. 2016 Jun;74(6):948-54. Review. Japanese. PMID: 27311184
8:Pharmacokinetic and Pharmacodynamic Analyses of Drug-Drug Interactions between Iguratimod and Warfarin. Yamamoto T, Hasegawa K, Onoda M, Tanaka K.Yakugaku Zasshi. 2016;136(6):905-11. doi: 10.1248/yakushi.15-00261. PMID: 27252068 Free Article
9:Pneumocystis jirovecii pneumonia developed in a patient with rheumatoid arthritis after 14 weeks of iguratimod add-on to treatment with methotrexate and etanercept. Arita Y, Taguchi H, Kobayashi M, Tono T, Ohsone Y, Okano Y.Mod Rheumatol. 2016 May 16:1-3. [Epub ahead of print] PMID: 27180974
10:Iguratimod (T-614) suppresses RANKL-induced osteoclast differentiation and migration in RAW264.7 cells via NF-κB and MAPK pathways. Gan K, Yang L, Xu L, Feng X, Zhang Q, Wang F, Tan W, Zhang M.Int Immunopharmacol. 2016 Jun;35:294-300. doi: 10.1016/j.intimp.2016.03.038. Epub 2016 Apr 16. PMID: 27085680