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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
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 Click here for help
INN number INN
9566 ibrutinib
Synonyms Click here for help
Imbruvica® | PCI-32765
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678901
Reactome Reaction Reactome logo R-HSA-9679028
Other databases
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
Search Google for chemicals with the same backbone XYFPWWZEPKGCCK
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SynPHARM 84487 (in complex with Bruton tyrosine kinase)
UniChem Compound Search for chemical match using the InChIKey XYFPWWZEPKGCCK-GOSISDBHSA-N
UniChem Connectivity Search for chemical match using the InChIKey XYFPWWZEPKGCCK-GOSISDBHSA-N
Wikipedia Ibrutinib

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Tocris
Ibrutinib (links to external site)
Cat. No. 6813