Wednesday, January 21, 2015


Common name: Afatinib; BIBW-2992; BIBW2992; Tomtovok; Tovok; Gilotrif; Giotrif; Afatinib dimaleate 
Trademarks:  Tomtovok; Tovok; Gilotrif; Giotrif
Molecular Formula: C24H25ClFN5O3
CAS Registry Number: 439081-18-2; 850140-72-6; 850140-73-7(dimaleate)
CAS Name: N-[4-[(3-Chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4(dimethylamino)-2-butenamide
Molecular Weight: 485.937
InChI: InChI=1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/b4-3+/t16-/m0/s1
Activity: Tyrosine Kinase Inhibitor; Protein Kinase Inhibitor;  EGFR Kinase Inhibitor; ERBB2 Kinase Inhibitor; ERBB4 Kinase Inhibitor; NSCLC Therapy; Metastatic NSCLC Therapy; Treatment for EGFR positive Mutation; Dual Receptor Tyrosine Kinase Inhibitor; Cancer Therapy
Status: Launched 2013 (US and EU)
Originator: Boehringer Ingelheim

Afatinib synthesis: WO2002050043A1

Afatinib synthesis: WO2005037824A2

Orange Book says for Afatinib:
US8426586 expires (expected) Oct 10, 2029

1. Himmelsbach, F.; et. al. Quinazoline derivatives, these drug-containing compounds, their use and process for their production. WO2002050043A1
2. Rall, W.; et. al. Method for the production of amino crotonyl compounds. WO2005037824A2
3.Li, D.; et. al. BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models. Oncogene 2008, 27(34), 4702-4711. (activity)
4. Johnson, M.; et. al. Afatinib: emerging next-generation tyrosine kinase inhibitor for NSCLC. Onco Targets Ther 2013, 6, 135-143. (activity)
5. Castaner, R. et. al. BIBW-2992. Dual EGFR/HER2 inhibitor, oncolytic. Drugs Fut 2008, 33(8), 649.
6. Bruns, A.; et. al. Crystalline forms of afatinib di-maleate. WO2013052157A1