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SML3073

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C32H33ClFN5O11
CAS Number:
850140-73-7
Molecular Weight:
718.08
MDL number:
MFCD25974239
UNSPSC Code:
12352200
NACRES:
NA.77

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

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.).

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - STOT RE 2

target_organs

Kidney,Skin

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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