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
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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
Immunopharmacology Comments
Ibrutinib inhibits BTK-mediated regulation of critical B cell pro-survival mechanisms, leading to decreased B cell activity and increased B cell apoptosis. This mechanism is exploited clinically for the treatment of B cell malignancies and to manage chronic GvHD.
Immunopharmacology Disease
Disease X-Refs Comment References
Graft versus host disease Approved drug for chronic GvHD.
Chronic lymphocytic leukemia Disease Ontology: DOID:1040
OMIM: 151400
Orphanet: ORPHA67038
Approved drug for CLL.
Mantle cell lymphoma Disease Ontology: DOID:0050746
Orphanet: ORPHA52416
Approved drug for MCL.
Waldenstrom macroglobulinemia Disease Ontology: DOID:0050747
OMIM: 153600
Orphanet: ORPHA33226
Approved drug for WM.