ibrutinib   Click here for help

GtoPdb Ligand ID: 6912

Synonyms: Imbruvica® | PCI-32765
Approved drug PDB Ligand Immunopharmacology Ligand
ibrutinib is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Ibrutinib is a clinically used inhibitor of Bruton's tyrosine kinase. It was originally approved with breakthrough therapy designation through the FDA's accelerated approval program.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 99.16
Molecular weight 440.2
XLogP 4.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C=CC(=O)N1CCCC(C1)n1nc(c2c1ncnc2N)c1ccc(cc1)Oc1ccccc1
Isomeric SMILES C=CC(=O)N1CCC[C@H](C1)n1nc(c2c1ncnc2N)c1ccc(cc1)Oc1ccccc1
InChI InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1
InChI Key XYFPWWZEPKGCCK-GOSISDBHSA-N
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
BLK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 9.3 – 10.0 pIC50 - 2-3
pIC50 10.0 (IC50 1x10-10 M) [2]
pIC50 9.3 (IC50 5x10-10 M) [3]
BMX non-receptor tyrosine kinase Hs Inhibitor Inhibition 9.1 pIC50 - 2-3
pIC50 9.1 (IC50 8x10-10 M) [3]
pIC50 9.1 (IC50 8x10-10 M) [2]
Bruton tyrosine kinase Primary target of this compound Hs Inhibitor Inhibition 8.8 – 9.3 pIC50 - 2,4
pIC50 9.3 (IC50 5x10-10 M) [4]
pIC50 8.8 (IC50 1.5x10-9 M) [2]
TXK tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 2
pIC50 8.7 (IC50 2x10-9 M) [2]
YES proto-oncogene 1, Src family tyrosine kinase Hs Inhibitor Inhibition 8.4 pIC50 - 2
pIC50 8.4 (IC50 4.1x10-9 M) [2]
IL2 inducible T cell kinase Hs Inhibitor Inhibition 8.3 pIC50 - 2
pIC50 8.3 (IC50 4.9x10-9 M) [2]
LCK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 8.2 pIC50 - 2
pIC50 8.2 (IC50 6.3x10-9 M) [2]
tec protein tyrosine kinase Hs Inhibitor Inhibition 8.1 pIC50 - 2
pIC50 8.1 (IC50 7x10-9 M) [2]
SRC proto-oncogene, non-receptor tyrosine kinase Hs Inhibitor Inhibition 7.7 pIC50 - 2
pIC50 7.7 (IC50 1.9x10-8 M) [2]
LYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.7 pIC50 - 2
pIC50 7.7 (IC50 2x10-8 M) [2]
FYN proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.5 pIC50 - 2
pIC50 7.5 (IC50 2.9x10-8 M) [2]
HCK proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 7.5 pIC50 - 2
pIC50 7.5 (IC50 2.9x10-8 M) [2]
Janus kinase 3 Hs Inhibitor Inhibition 7.5 pIC50 - 2
pIC50 7.5 (IC50 3.2x10-8 M) [2]
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
erb-b2 receptor tyrosine kinase 4 Hs Inhibitor Inhibition 8.5 pIC50 - 2
pIC50 8.5 (IC50 3.4x10-9 M) [2]
epidermal growth factor receptor Hs Inhibitor Inhibition 8.3 pIC50 - 2
pIC50 8.3 (IC50 5.3x10-9 M) [2]
erb-b2 receptor tyrosine kinase 2 Hs Inhibitor Inhibition 8.2 pIC50 - 2
pIC50 8.2 (IC50 6.4x10-9 M) [2]