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
Pronunciationdak" oh mi' ti nib
Trade namesVizimpro
Other namesPF-00299804
AHFS/Drugs.comMonograph
MedlinePlusa618055
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80%
Protein binding98%
MetabolismCYP2D6, CYP3A4
MetabolitesO-desmethyl-dacomitinib
Elimination half-life70 hrs
Excretion79% 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H25ClFN5O2
Molar mass469.95 g·mol−1
3D model (JSmol)
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. The January 2014 results of the first trials were disappointing, with a failure to meet the study goals.[4][5][6] Additional Phase III trials are ongoing.[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.

References
  1. "Vizimpro Product information". Health Canada. 25 April 2012. Retrieved 29 May 2022.
  2. "Summary Basis of Decision (SBD) for Verzenio". Health Canada. 23 October 2014. Retrieved 29 May 2022.
  3. "Dacomitinib". NCI Drug Dictionary. National Cancer Institute, U.S. Department of Health and Human Services.
  4. Chustecka Z (27 January 2014). "Dacomitinib Fails in Pretreated Non-small Cell Lung Cancer". Medscape.
  5. Taylor P (28 January 2014). "Blow to Pfizer as dacomitinib fails in lung cancer trials". pmlive.com.
  6. "Pfizer Announces Top-Line Results From Two Phase 3 Trials Of Dacomitinib In Patients With Refractory Advanced Non-Small Cell Lung Cancer". Pfizer Press Release. 27 January 2014.
  7. Smith M (6 June 2017). "Dacomitinib Sets PFS Record in Phase III NSCLC Trial". MedPage Today.
  8. Shirley M (December 2018). "Dacomitinib: First Global Approval". Drugs. 78 (18): 1947–1953. doi:10.1007/s40265-018-1028-x. PMID 30506139. S2CID 54034570.
  9. "Vizimpro EPAR". European Medicines Agency (EMA). 5 June 2019. Retrieved 13 December 2019.
  • "Dacomitinib". Drug Information Portal. U.S. National Library of Medicine.


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