ibrutinib   

GtoPdb Ligand ID: 6912

Synonyms: Imbruvica® | PCI-32765
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
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
IUPAC Name
1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
International Nonproprietary Names
INN number INN
9566 ibrutinib
Synonyms
Imbruvica® | PCI-32765
Database Links
CAS Registry No. 936563-96-1 (source: SciFinder)
ChEMBL Ligand CHEMBL1873475
DrugCentral Ligand 4810
GtoPdb PubChem SID 178103494
PubChem CID 24821094
RCSB PDB Ligand 1E8
Search Google for chemical match using the InChIKey XYFPWWZEPKGCCK-GOSISDBHSA-N
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Search UniChem for chemical match using the InChIKey XYFPWWZEPKGCCK-GOSISDBHSA-N
Search UniChem for chemicals with the same backbone XYFPWWZEPKGCCK
SynPHARM 84487 (in complex with Bruton tyrosine kinase)
Wikipedia Ibrutinib

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Tocris
Ibrutinib
Cat. No. 6813