Dacomitinib

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.^[3]

Dacomitinib

Clinical data
Pronunciation	dak" oh mi' ti nib
Trade names	Vizimpro
Other names	PF-00299804
AHFS/Drugs.com	Monograph
MedlinePlus	a618055
License data	US DailyMed: Dacomitinib
Routes of administration	By mouth
ATC code	L01EB07 (WHO)
Legal status
Legal status	CA: ℞-only[1][2] US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	80%
Protein binding	98%
Metabolism	CYP2D6, CYP3A4
Metabolites	O-desmethyl-dacomitinib
Elimination half-life	70 hrs
Excretion	79% faeces, 3% urine
Identifiers
IUPAC name (2E)-N-{4-[(3-Chloro-4-fluorophenyl)amino]-7-methoxy-6-quinazolinyl}-4-(1-piperidinyl)-2-butenamide
CAS Number	1110813-31-4 Y
PubChem CID	11511120
IUPHAR/BPS	7422
DrugBank	DB11963
ChemSpider	9685914
UNII	2XJX250C20
KEGG	D09883 as salt: D10514
ChEBI	CHEBI:132268
ChEMBL	ChEMBL2105719
PDB ligand	1C9 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID50149493
Chemical and physical data
Formula	C24H25ClFN5O2
Molar mass	469.95 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C2C(=C1)N=CN=C2NC3=CC(=C(C=C3)F)Cl)NC(=O)/C=C/CN4CCCCC4
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+ Key:LVXJQMNHJWSHET-AATRIKPKSA-N

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,^[4][5][6] but additional Phase III trials continued.^[4] In 2017, results of a trial comparing dacomitinib to gefitinib for NSCLC (driven by mutated EGFR) were announced.^[7]

Dacomitinib was approved for medical use in the United States in September 2018,^[8] in Japan in 2019, and in the European Union in 2019;^[9] for the treatment of non-small cell lung cancer with epidermal growth factor receptor (EGFR) gene mutation.