DABRAFENIB

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Synonyms
Status
Molecule Category Free-form
ATC L01EC02
UNII QGP4HA4G1B
EPA CompTox DTXSID20152499

Structure

InChI Key BFSMGDJOXZAERB-UHFFFAOYSA-N
Smiles CC(C)(C)c1nc(-c2cccc(NS(=O)(=O)c3c(F)cccc3F)c2F)c(-c2ccnc(N)n2)s1
InChI
InChI=1S/C23H20F3N5O2S2/c1-23(2,3)21-30-18(19(34-21)16-10-11-28-22(27)29-16)12-6-4-9-15(17(12)26)31-35(32,33)20-13(24)7-5-8-14(20)25/h4-11,31H,1-3H3,(H2,27,28,29)

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H20F3N5O2S2
Molecular Weight 519.57
AlogP 5.36
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 110.86
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 35.0
Assay Description Organism Bioactivity Reference
In vivo inhibition of B-Raf V600E mutant-mediated ERK1/2 phosphorylation in tumor of CD1 nu/nu mouse bearing B-Raf V600E mutant harboring human A375P-F11 cells at => 3 mg/kg, po administered as single dose measured after 2 to 6 hrs by duplex ELISA Mus musculus 50.0 %
Inhibition of B-Raf V600E mutant in human HepG2 cells assessed as decrease in ERK phosphorylation Homo sapiens 4.0 nM
Inhibition of human COLO205 cell proliferation Homo sapiens 7.0 nM
Inhibition of B-Raf V600E mutant-driven A375P-F11 cell proliferation Homo sapiens 8.0 nM
Inhibition of B-Raf V600E mutant-driven SK-MEL-28 cell proliferation after 72 hrs by CellTiter-Glo luminescent assay Homo sapiens 3.0 nM
Inhibition of B-Raf V600E mutant in human SK-MEL-28 cells assessed as decrease in ERK phosphorylation incubated for 1 hr by immunoassay Homo sapiens 4.0 nM
Inhibition of N-terminal His tagged B-Raf V600E mutant (unknown origin) expressed in baculovirus infected insect cells co-expressing CDC37 assessed as decrease in biotinylated-MEK protein phosphorylation by AlphaScreen assay Homo sapiens 0.7 nM
Inhibition of wild type BRAF (unknown origin) assessed as ADP formation measured for 5 hrs by pyruvate kinase/lactate dehydrogenase coupled assay in presence of ATP, MEK1, NADH Homo sapiens 9.7 nM
Inhibition of BRAF V600E mutant in human A375 cells assessed as inhibition of ERK phosphorylation measured after 72 hrs by ELISA assay Homo sapiens 11.0 nM
Competitive binding affinity to ARAF in human A375 cells after 15 mins in presence of ATP analogue Homo sapiens 26.0 nM
Competitive binding affinity to BRAF in human A375 cells after 15 mins in presence of ATP analogue Homo sapiens 6.0 nM
Competitive binding affinity to CRAF in human A375 cells after 15 mins in presence of ATP analogue Homo sapiens 150.0 nM
Inhibition of wild type B-Raf (unknown origin) assessed as MEK1 phosphorylation using MEK1-Avitag as substrate after 1 hr by HTRF assay Homo sapiens 0.4 nM
Inhibition of B-Raf V600E mutant (unknown origin) assessed as MEK1 phosphorylation using MEK1-Avitag as substrate after 1 hr by HTRF assay Homo sapiens 1.0 nM
Inhibition of wild type B-Raf in human MIAPaCa2 cells assessed as reduction in ERK phosphorylation preincubated for 1 hr by Western blot method Homo sapiens 529.0 nM
Inhibition of B-Raf V600E mutant in human A375 cells assessed as ERK phosphorylation preincubated for 1 hr by Western blot method Homo sapiens 1.0 nM
Inhibition of recombinant human N-terminal GST-6His tagged BRAF V600E mutant (417 to 766 residues) expressed in baculovirus infected Sf9 cells preincubated with substrate followed by protein and ATP addition measured after 60 mins by scintillation counter method Homo sapiens 9.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 305.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 601.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 47.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 22.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 364.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 13.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 36.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 19.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 126.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 318.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 851.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 949.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 705.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 412.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 116.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 727.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 817.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 783.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 33.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 82.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 477.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 53.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 520.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 34.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 120.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 106.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 283.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 649.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 66.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 188.0 nM
Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase inhibitors, used to assess residual binding of ~300 proteins simultaneously from cell lysate in the presence of a compound. Quantitative readout performed by mass spectrometry. Homo sapiens 184.0 nM
Inhibition of BRAF V600E mutant (unknown origin) Homo sapiens 0.8 nM
Inhibition of BRAF V600E mutant in human A375 cells assessed as reduction in ERK phosphorylation by Western blot analysis Homo sapiens 4.0 nM
Cytotoxicity against human SK-MEL-28 cells after 72 hrs by CellTiter-Glo assay Homo sapiens 43.0 nM
Inhibition of B-Raf V600E mutant (unknown origin) using fluorescein-MAP2K1 as substrate after 1 hr by electrophoretic assay Homo sapiens 0.7 nM Inhibition of B-Raf V600E mutant (unknown origin) using fluorescein-MAP2K1 as substrate after 1 hr by electrophoretic assay Homo sapiens 0.7079 nM
Inhibition of B-Raf V600E mutant (unknown origin) at 10 uM using fluorescein-MAP2K1 as substrate after 1 hr by electrophoretic assay relative to control Homo sapiens 40.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -6.57 %
Inhibition of recombinant human full length GST-tagged BRAF expressed in baculovirus expression system Homo sapiens 5.0 nM
Inhibition of recombinant human GST-tagged BRAF V600E mutant expressed in baculovirus expression system Homo sapiens 1.0 nM
Inhibition of human full length N-terminal GST-tagged RIPK3 expressed in baculovirus infected sf9 insect cells assessed as reduction in MBP phosphorylation using MBP as substrate by kinase-Glo luminescence assay Homo sapiens 250.0 nM
Inhibition of human RIPK3 using MBP as substrate by [gamma33-ATP] based radiometric assay Homo sapiens 2.0 nM
Inhibition of human RIPK2 using MBP as substrate by [gamma33-ATP] based radiometric assay Homo sapiens 77.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.96 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.767 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.1 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 6.09 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 6.09 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.1 %
Inhibition of BRAF V600E mutant (unknown origin) Homo sapiens 0.5 nM
Inhibition of BRAF V600E mutant (unknown origin) Homo sapiens 0.7 nM
Inhibition of BRAF V600E mutant (unknown origin) Homo sapiens 0.7 nM

Cross References

Resources Reference
ChEBI 75045
ChEMBL CHEMBL2028663
DrugBank DB08912
DrugCentral 4801
FDA SRS QGP4HA4G1B
Guide to Pharmacology 6494
PDB P06
PubChem 44462760
SureChEMBL SCHEMBL806377
ZINC ZINC000068153186
CONTENTS