iguratimod   Click here for help

GtoPdb Ligand ID: 9736

Synonyms: Careram® | Iremod | Kolbet® | T-614
Approved drug PDB Ligand Immunopharmacology Ligand
iguratimod is an approved drug (China (2011), Japan (2012))
Compound class: Synthetic organic
Comment: Iguratimod is a methanesulfonanilide disease-modifying anti-rheumatic drug [1,5-6]. Evidence from a mouse colitis model shows an anti-inflammatory effect of iguratimod, partly via regulation of Th17/Treg cells [4], that suggest iguratimod as a novel therapeutic for the treatment of IBD.

iguratimod is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 123.09
Molecular weight 374.06
XLogP 2.78
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=CNc1coc2c(c1=O)cc(c(c2)NS(=O)(=O)C)Oc1ccccc1
Isomeric SMILES O=CNc1coc2c(c1=O)cc(c(c2)NS(=O)(=O)C)Oc1ccccc1
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)
InChI Key ANMATWQYLIFGOK-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Aikawa Y, Yamamoto M, Yamamoto T, Morimoto K, Tanaka K. (2002)
An anti-rheumatic agent T-614 inhibits NF-kappaB activation in LPS- and TNF-alpha-stimulated THP-1 cells without interfering with IkappaBalpha degradation.
Inflamm Res, 51 (4): 188-94. [PMID:12058956]
2. Bloom J, Metz C, Nalawade S, Casabar J, Cheng KF, He M, Sherry B, Coleman T, Forsthuber T, Al-Abed Y. (2016)
Identification of Iguratimod as an Inhibitor of Macrophage Migration Inhibitory Factor (MIF) with Steroid-sparing Potential.
J Biol Chem, 291 (51): 26502-26514. [PMID:27793992]
3. Greven D, Leng L, Bucala R. (2010)
Autoimmune diseases: MIF as a therapeutic target.
Expert Opin Ther Targets, 14 (3): 253-64. [PMID:20148714]
4. Jiang XP, Huang XL, Yang ZP, Wang SC, Xie W, Miao L, Tang L, Huang ZM. (2018)
Iguratimod ameliorates inflammatory responses by modulating the Th17/Treg paradigm in dextran sulphate sodium-induced murine colitis.
Mol Immunol, 93: 9-19. [PMID:29121519]
5. Luo Q, Sun Y, Liu W, Qian C, Jin B, Tao F, Gu Y, Wu X, Shen Y, Xu Q. (2013)
A novel disease-modifying antirheumatic drug, iguratimod, ameliorates murine arthritis by blocking IL-17 signaling, distinct from methotrexate and leflunomide.
J Immunol, 191 (10): 4969-78. [PMID:24123677]
6. Mucke HA. (2012)
Iguratimod: a new disease-modifying antirheumatic drug.
Drugs Today, 48 (9): 577-86. [PMID:23032798]