Afatinib (BIBW2992) Dimaleate

Description: Afatinib dimaleate (the maleate salt form of Afatinib, also know as BIBW-2992; BIBW2992) is a potent, covalent/irreversible, and orally bioavailable dual EGFR/HER2 receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Afatinib is an FDA approved anticancer drug used to treat non-small cell lung carcinoma (NSCLC). It is sold under the brand name of Gilotrif in the USA. It irreversibly binds to and inhibits EGFR/HER2 including EGFR(wt), EGFR(L858R), EGFR(L858R/T790M) and HER2 with IC50 of 0.5 nM, 0.4 nM, 10 nM and 14 nM in cell-free assays, respectively; and is 100-fold more active against Gefitinib-resistant L858R-T790M EGFR mutant.

References: Oncogene. 2008 Aug 7; 27(34):4702-11; Br J Cancer. 2008 Jan 15; 98(1):80-5.

Related CAS: 439081-18-2 (free base); 850140-73-7 (dimaleate); 850140-72-6 (free base)

Chemical Name: (S, E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide dimaleate

InChi Key: USNRYVNRPYXCSP-JUGPPOIOSA-N

InChi Code: InChI=1S/C24H25ClFN5O3.2C4H4O4/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; 2*5-3(6)1-2-4(7)8/h3-6, 10-12, 14, 16H, 7-9, 13H2, 1-2H3, (H, 30, 32)(H, 27, 28, 29); 2*1-2H, (H, 5, 6)(H, 7, 8)/b4-3+; 2*2-1-/t16-; ; /m0../s1

SMILES Code: O=C(NC1=CC2=C(NC3=CC=C(F)C(Cl)=C3)N=CN=C2C=C1O[CH]4COCC4)/C=C/CN(C)C.O=C(O)/C=C\C(O)=O.O=C(O)/C=C\C(O)=O