pamapimod   

GtoPdb Ligand ID: 9915

Synonyms: compound 2b [PMID: 21375264] | Ro 4402257 | Ro-4402257 | Ro4402257
Compound class: Synthetic organic
Comment: Pamapimod is an ATP-competitive (Type I), orally bioavailable and highly selective inhibitor of p38α mitogen-activated protein kinase (MAPK14), that was developed for immunomodulatory potential [4].
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 109.5
Molecular weight 406.15
XLogP 3.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCCC(Nc1ncc2c(n1)n(C)c(=O)c(c2)Oc1ccc(cc1F)F)CCO
Isomeric SMILES OCCC(Nc1ncc2c(n1)n(C)c(=O)c(c2)Oc1ccc(cc1F)F)CCO
InChI InChI=1S/C19H20F2N4O4/c1-25-17-11(10-22-19(24-17)23-13(4-6-26)5-7-27)8-16(18(25)28)29-15-3-2-12(20)9-14(15)21/h2-3,8-10,13,26-27H,4-7H2,1H3,(H,22,23,24)
InChI Key JYYLVUFNAHSSFE-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Pamapimod reached Phase 2 clinical evaluation as an immunomodulator for rheumatoid arthritis, but development was terminated due to a lack of clinical efficacy, either as a monotherapy, or as an adjunct to methotrexate [1,3].
Mechanism Of Action and Pharmacodynamic Effects
The ratinale for inhibiting p38 MAPK as a novel apporach for the treatment of rheumatoid arthritis is discussed in [5] and [2].