losmapimod   Click here for help

GtoPdb Ligand ID: 7835

Synonyms: GS856553 | GW856553
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Losmapimod is a p38 mitogen-activated kinase α/β inhibitor. It was originally developed by GlaxoSmithKline for cardiovascular disease, but this failed to show efficacy. Fulcrum acquired the drug and are repurposing it for the treatment of the progressive muscle wasting disorder facioscapulohumeral muscular dystrophy (FSHD) based on evidence that p38α regulates expression of the FSHD-related gene DUX4 [4-5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 71.09
Molecular weight 383.2
XLogP 4.01
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1ccc(nc1)c1cc(cc(c1C)F)C(=O)NC1CC1)NCC(C)(C)C
Isomeric SMILES O=C(c1ccc(nc1)c1cc(cc(c1C)F)C(=O)NC1CC1)NCC(C)(C)C
InChI InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)
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Molecular structure representations generated using Open Babel