dacomitinib

Ligand id: 7422

Name: dacomitinib

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 79.38
Molecular weight 469.17
XLogP 3.93
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(E)-N-[4-[(3-chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-yl]-4-piperidin-1-ylbut-2-enamide
International Nonproprietary Names
INN number INN
9314 dacomitinib
Synonyms
PF-00299804
Comments
Dacomitinib is a second-generation, irreversible pan inhibitor of HER tyrosine kinases (EGFR, and ERBBs) that is being developed by Pfizer.
Results from the ARCHER 1050 Phase 3 randomised, open-label trial (NCT01774721) that directly compared dacomitinib against gefitinib, as first-line treatment for patients with EGFR-mutation +ve non-small-cell lung cancer (NSCLC), reported that dacomitinib significantly increased progression-free survival and overall survival compared to gefitinib [2]. However, dacomitinib's use may be limited in NSCLC patients with brain metastases, as these patients we excluded from the trial because dacomitinib's ability to cross the blood-brain-barrier has not been fully confirmed. This is unlike osimertinib (a third-generation irreversible EGFR inhibitor) which has confirmed brain penetrance, and which does not appear to cause the same dose-limiting toxicities that afflict dacomitinib. Pfizer posted a press release in April 2018 which reported that both the FDA and EMA had accepted regulatory submissions (New Drug Application and Marketing Authorization Application respectively) for review of dacomitinib as a therapy for metastatic NSCLC with EGFR-activating mutations. The FDA granted Priority Review status for the submitted NDA.
Database Links
CAS Registry No. 1110813-31-4
ChEMBL Ligand CHEMBL2110732
GtoPdb PubChem SID 178103994
PubChem CID 11511120
RCSB PDB Ligand 1C9
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Wikipedia Dacomitinib

Product suppliers

Tocris
Dacomitinib
Cat. No. 6231