revamilast   Click here for help

GtoPdb Ligand ID: 9865

Synonyms: Example 26 [WO2006064355A2] | GRC 4039 | GRC-4039 | GRC4039
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Revamilast (GRC 4039) is an orally active, selective phosphodiesterase IV (PDE4) inhibitor, that was developed by Glenmark Pharmaceuticals for the treatment of multiple inflammatory conditions (rheumatoid arthritis (RA), asthma, chronic obstructive pulmonary disease (COPD) , multiple sclerosis, osteoarthritis, neuropathic pain). The chemical structure is claimed as Example 26 in Glenmark patent WO2006064355A2 [1]. GRC 4039 is no longer listed on Glenmark's development pipeline webpage.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 89.85
Molecular weight 438.99
XLogP 4.13
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES FC(Oc1ccc(c2c1oc1c2cncc1)C(=O)N=c1c(Cl)cn(cc1Cl)O)F
Isomeric SMILES FC(Oc1ccc(c2c1oc1c2cncc1)C(=O)N=c1c(Cl)cn(cc1Cl)O)F
InChI InChI=1S/C18H9Cl2F2N3O4/c19-10-6-25(27)7-11(20)15(10)24-17(26)8-1-2-13(29-18(21)22)16-14(8)9-5-23-4-3-12(9)28-16/h1-7,18,27H
InChI Key CFRXVFRHMZLQBS-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-6-(difluoromethoxy)-[1]benzoxolo[3,2-c]pyridine-9-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9210 revamilast
Synonyms Click here for help
Example 26 [WO2006064355A2] | GRC 4039 | GRC-4039 | GRC4039
Database Links Click here for help
CAS Registry No. 893555-90-3 (source: WHO INN record)
DrugBank Ligand DB11838
GtoPdb PubChem SID 363894159
PubChem CID 11546664
Search Google for chemical match using the InChIKey CFRXVFRHMZLQBS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CFRXVFRHMZLQBS
Search PubMed clinical trials revamilast
Search PubMed titles revamilast
Search PubMed titles/abstracts revamilast
Search UniChem for chemical match using the InChIKey CFRXVFRHMZLQBS-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone CFRXVFRHMZLQBS