CHEBI:76612 - ibrutinib

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ChEBI Name ibrutinib
ChEBI ID CHEBI:76612
Definition A member of the class of acrylamides that is (3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine in which the piperidine nitrogen is replaced by an acryloyl group. A selective and covalent inhibitor of the enzyme Bruton's tyrosine kinase, it is used for treatment of B-cell malignancies.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB81565483, ChemicalBook:CB4506696, eMolecules:10748986, Selleckchem:Dasatinib, ZINC000003986735
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Dasatinib, sold under the brand name Sprycel among others, is a targeted therapy medication used to treat certain cases of chronic myelogenous leukemia (CML) and acute lymphoblastic leukemia (ALL). Specifically it is used to treat cases that are Philadelphia chromosome-positive (Ph+). It is taken by mouth. Common adverse effects include low white blood cells, low blood platelets, anemia, swelling, rash, and diarrhea. Severe adverse effects may include bleeding, pulmonary edema, heart failure, and prolonged QT syndrome. Use during pregnancy may result in harm to the fetus. It is a tyrosine-kinase inhibitor and works by blocking a number of tyrosine kinases such as Bcr-Abl and the Src kinase family. Dasatinib was approved for medical use in the United States and in the European Union in 2006. It is on the World Health Organization's List of Essential Medicines.
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Formula C25H24N6O2
Net Charge 0
Average Mass 440.49710
Monoisotopic Mass 440.19607
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
InChIKey XYFPWWZEPKGCCK-GOSISDBHSA-N
SMILES Nc1ncnc2n(nc(-c3ccc(Oc4ccccc4)cc3)c12)[C@@H]1CCCN(C1)C(=O)C=C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing ibrutinib (CHEBI:76612) has role antineoplastic agent (CHEBI:35610)
ibrutinib (CHEBI:76612) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
ibrutinib (CHEBI:76612) is a N-acylpiperidine (CHEBI:48591)
ibrutinib (CHEBI:76612) is a acrylamides (CHEBI:22216)
ibrutinib (CHEBI:76612) is a aromatic amine (CHEBI:33860)
ibrutinib (CHEBI:76612) is a aromatic ether (CHEBI:35618)
ibrutinib (CHEBI:76612) is a pyrazolopyrimidine (CHEBI:38669)
ibrutinib (CHEBI:76612) is a tertiary carboxamide (CHEBI:140326)
IUPAC Name
1-{(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}prop-2-en-1-one
INNs Sources
ibrutinib WHO MedNet
ibrutinib WHO MedNet
ibrutinib WHO MedNet
ibrutinibum WHO MedNet
Synonyms Sources
ibrutinib UniProt
PCI 32765 ChemIDplus
PCI-32765 ChemIDplus
PCI32765 ChemIDplus
Brand Name Source
IMBRUVICA KEGG DRUG
Manual Xrefs Databases
4810 DrugCentral
D10223 KEGG DRUG
Ibrutinib Wikipedia
US2008076921 Patent
US2012053189 Patent
US20130178483 Patent
US2013079327 Patent
US2013178483 Patent
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Registry Numbers Types Sources
13102252 Reaxys Registry Number Reaxys
936563-96-1 CAS Registry Number KEGG DRUG
936563-96-1 CAS Registry Number ChemIDplus
Citations Types Sources
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Last Modified
07 March 2018