SML3073

Afatinib dimaleate

≥98% (HPLC)

• Synonym(s): (2E)-N-[4-[(3-Chloro-4-fluorophenyl)amino]­-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-butenamide, (2Z)-2-butenedioate (1:2), (S,E)-N-(4-(3-Chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide dimaleate, BIBW 2992 dimaleate, BIBW-2992 dimaleate, BIBW2992 dimaleate
• Empirical Formula (Hill Notation): C₃₂H₃₃ClFN₅O₁₁
• CAS Number: 850140-73-7
• Molecular Weight: 718.08
• MDL number: MFCD25974239
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: H₂O: 2 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: OC(/C=C\C(O)=O)=O.OC(/C=C\C(O)=O)=O.CN(C)C/C=C/C(NC1=CC(C(NC2=CC=C(F)C(Cl)=C2)=NC=N3)=C3C=C1O[C@H]4CCOC4)=O
• 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
• InChI key: USNRYVNRPYXCSP-JUGPPOIOSA-N

Description

Biochem/physiol Actions

Afatinib (BIBW2992) is an orally active, irreversible, potent and selective EGFR/HER2 (ErbB2) dual inhibitor (EGFR IC50 = 0.5 nM (Wt), 0.4 nM (L858R), 10 nM (L858R/T790M); HER2 IC50 = 14 nM) that covalently targets EGFR Cys773 and HER2 Cys805 residues. BIBW2992 suppresses 100 ng/mL EGF-induced EGFR/HER2 tyrosin phosphorylation (IC50 = 13-71 nM; A431, NIH-3T3-HER2, BT-474, NCI-N87), inhibits cancer cells survival in cultures and induces tumor regression in xenograft and transgenic lung cancer models in vivo (20 mg/kg/day p.o.).

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302,H319,H373
• pcodes: P260 - P264 - P270 - P301 + P312 - P305 + P351 + P338 - P314
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - STOT RE 2
• target_organs: Kidney,Skin
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable