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
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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)
1. Hafner FT, Werner D, Kaiser M. (2014)
Determination of regorafenib (BAY 73-4506) and its major human metabolites BAY 75-7495 (M-2) and BAY 81-8752 (M-5) in human plasma by stable-isotope dilution liquid chromatography-tandem mass spectrometry.
Bioanalysis, 6 (14): 1923-37. [PMID:25158964]
2. Wilhelm SM, Dumas J, Adnane L, Lynch M, Carter CA, Schütz G, Thierauch KH, Zopf D. (2011)
Regorafenib (BAY 73-4506): a new oral multikinase inhibitor of angiogenic, stromal and oncogenic receptor tyrosine kinases with potent preclinical antitumor activity.
Int J Cancer, 129 (1): 245-55. [PMID:21170960]
3. Zambon A, Niculescu-Duvaz I, Niculescu-Duvaz D, Marais R, Springer CJ. (2012)
Small molecule inhibitors of BRAF in clinical trials.
Bioorg Med Chem Lett, 22 (2): 789-92. [PMID:22222036]