CHEBI:132268 - dacomitinib

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ChEBI Name dacomitinib
ChEBI ID CHEBI:132268
Definition A member of the class of quinazolines that is 7-methoxyquinazoline-4,6-diamine in which the amino group at position 4 is substituted by a 3-chloro-4-fluorophenyl group and the amino group at position 6 is substituted by an (E)-4-(piperidin-1-yl)but-2-enoyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB22566418, Selleckchem:pf299804, ZINC000072266312
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Dacomitinib, sold under the brand name Vizimpro, is a medication for the treatment of non-small-cell lung carcinoma (NSCLC). It is a selective and irreversible inhibitor of EGFR. Dacomitinib has advanced to several Phase III clinical trials. In January 2014, results of the first trials were disappointing, with a failure to meet the study goals, but additional Phase III trials continued. In 2017, results of a trial comparing dacomitinib to gefitinib for NSCLC (driven by mutated EGFR) were announced. Dacomitinib was approved for medical use in the United States in September 2018, in Japan in 2019, and in the European Union in 2019; for the treatment of non-small cell lung cancer with epidermal growth factor receptor (EGFR) gene mutation.
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Formula C24H25ClFN5O2
Net Charge 0
Average Mass 469.940
Monoisotopic Mass 469.16808
InChI InChI=1S/C24H25ClFN5O2/c1-33-22-14-20-17(24(28-15-27-20)29-16-7-8-19(26)18(25)12-16)13-21(22)30-23(32)6-5-11-31-9-3-2-4-10-31/h5-8,12-15H,2-4,9-11H2,1H3,(H,30,32)(H,27,28,29)/b6-5+
InChIKey LVXJQMNHJWSHET-AATRIKPKSA-N
SMILES ClC=1C=C(NC2=NC=NC=3C2=CC(NC(=O)\C=C\CN4CCCCC4)=C(OC)C3)C=CC1F
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): epidermal growth factor receptor antagonist
An antagonist at the epidermal growth factor receptor.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing dacomitinib (CHEBI:132268) has role antineoplastic agent (CHEBI:35610)
dacomitinib (CHEBI:132268) has role epidermal growth factor receptor antagonist (CHEBI:74440)
dacomitinib (CHEBI:132268) is a enamide (CHEBI:51751)
dacomitinib (CHEBI:132268) is a monochlorobenzenes (CHEBI:83403)
dacomitinib (CHEBI:132268) is a monofluorobenzenes (CHEBI:83575)
dacomitinib (CHEBI:132268) is a piperidines (CHEBI:26151)
dacomitinib (CHEBI:132268) is a quinazolines (CHEBI:38530)
dacomitinib (CHEBI:132268) is a secondary amino compound (CHEBI:50995)
dacomitinib (CHEBI:132268) is a secondary carboxamide (CHEBI:140325)
dacomitinib (CHEBI:132268) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
(2E)-N-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]-4-(piperidin-1-yl)but-2-enamide
INNs Sources
dacomitinib WHO MedNet
dacomitinib WHO MedNet
dacomitinib WHO MedNet
dacomitinibum WHO MedNet
Synonyms Sources
PF 00299804-03 ChemIDplus
PF-00299804 ChEBI
PF-00299804-03 ChemIDplus
Manual Xrefs Databases
1C9 PDBeChem
D09883 KEGG DRUG
Dacomitinib Wikipedia
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Registry Numbers Types Sources
1110813-31-4 CAS Registry Number ChemIDplus
12400147 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
07 March 2018