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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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/)

✖
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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. China (2011)  |  Japan (2012)
IUPAC Name Click here for help
N-[7-methanesulfonamido-4-oxo-6-(phenoxy)chromen-3-yl]formamide
International Nonproprietary Names Click here for help
INN number INN
8176 iguratimod
Synonyms Click here for help
Careram® | Iremod | Kolbet® | T-614
Database Links Click here for help
CAS Registry No. 123663-49-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL2107455
DrugCentral Ligand 4894
GtoPdb PubChem SID 354702212
PubChem CID 124246
RCSB PDB Ligand 7TN
Search Google for chemical match using the InChIKey ANMATWQYLIFGOK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ANMATWQYLIFGOK
Search PubMed clinical trials iguratimod
Search PubMed titles iguratimod
Search PubMed titles/abstracts iguratimod
UniChem Compound Search for chemical match using the InChIKey ANMATWQYLIFGOK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ANMATWQYLIFGOK-UHFFFAOYSA-N

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

MedChemExpress
Iguratimod (links to external site)
Cat. No. HY-17009