regorafenib   Click here for help

GtoPdb Ligand ID: 5891

Synonyms: BAY 73-4506 | Stivarga®
Approved drug
regorafenib is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Regorafenib is an inhibitor of multiple membrane-bound and intracellular kinases. Although the drug is approved it must carry a Boxed Warning alerting patients and clinicians that severe and fatal liver toxicity was observed in some patients in regorafenib clinical studies. Regorafenib is a Type-2 kinase inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 92.35
Molecular weight 482.08
XLogP 3.91
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(=O)c1nccc(c1)Oc1ccc(c(c1)F)NC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
Isomeric SMILES CNC(=O)c1nccc(c1)Oc1ccc(c(c1)F)NC(=O)Nc1ccc(c(c1)C(F)(F)F)Cl
InChI InChI=1S/C21H15ClF4N4O3/c1-27-19(31)18-10-13(6-7-28-18)33-12-3-5-17(16(23)9-12)30-20(32)29-11-2-4-15(22)14(8-11)21(24,25)26/h2-10H,1H3,(H,27,31)(H2,29,30,32)
InChI Key FNHKPVJBJVTLMP-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2013))
IUPAC Name Click here for help
4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9026 regorafenib
Synonyms Click here for help
BAY 73-4506 | Stivarga®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9657514
Reactome Reaction Reactome logo R-HSA-6802938, R-HSA-9669854, R-HSA-9669900, R-HSA-9674430, R-HSA-9674095, R-HSA-9669870, R-HSA-9674408
Other databases
CAS Registry No. 755037-03-7 (source: SciFinder)
ChEBI CHEBI:68647
ChEMBL Ligand CHEMBL1946170
DrugBank Ligand DB08896
DrugCentral Ligand 4654
GtoPdb PubChem SID 178102514
PubChem CID 11167602
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Wikipedia Regorafenib