dacomitinib   Click here for help

GtoPdb Ligand ID: 7422

Synonyms: PF-00299804 | PF00299804 | Vizimpro®
Approved drug PDB Ligand
dacomitinib is an approved drug (FDA (2018), EMA (2019))
Compound class: Synthetic organic
Comment: Dacomitinib is a second-generation, irreversible pan inhibitor of HER tyrosine kinases (EGFR, and ERBBs) that was 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 [3]. Dacomitinib's use may be limited in NSCLC patients with brain metastases, as these patients were excluded from the trial because dacomitinib's ability to cross the blood-brain-barrier has not been fully confirmed. This is unlike osimertinib (another 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. In April 2018 both the FDA and EMA 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.

SARS-CoV-2: A high-throughput screen identified potential anti-SARS-CoV-2 activity in cell infection assays [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 79.38
Molecular weight 469.17
XLogP 3.97
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc2ncnc(c2cc1NC(=O)C=CCN1CCCCC1)Nc1ccc(c(c1)Cl)F
Isomeric SMILES COc1cc2ncnc(c2cc1NC(=O)/C=C/CN1CCCCC1)Nc1ccc(c(c1)Cl)F
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+
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2018), EMA (2019))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9314 dacomitinib
Synonyms Click here for help
PF-00299804 | PF00299804 | Vizimpro®
Database Links Click here for help
CAS Registry No. 1110813-31-4
ChEMBL Ligand CHEMBL2110732
DrugCentral Ligand 5297
GtoPdb PubChem SID 178103994
PubChem CID 11511120
RCSB PDB Ligand 1C9
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UniChem Compound Search for chemical match using the InChIKey LVXJQMNHJWSHET-AATRIKPKSA-N
UniChem Connectivity Search for chemical match using the InChIKey LVXJQMNHJWSHET-AATRIKPKSA-N
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Dacomitinib (links to external site)
Cat. No. 6231