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SML2259

Sigma-Aldrich

Lapatinib

≥98% (HPLC)

Synonym(s):

Lapatinib, GD 2016, GSK 572016, GW-572016, GW572016, N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine, N-(3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-((2-methylsulfonylethylamino)methyl)-2-furyl)quinazolin-4-amine

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About This Item

Empirical Formula (Hill Notation):
C29H26ClFN4O4S
CAS Number:
231277-92-2
Molecular Weight:
581.06
MDL number:
MFCD09264194
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CS(=O)(CCNCC1=CC=C(C2=CC=C3N=CN=C(C3=C2)NC4=CC=C(C(Cl)=C4)OCC5=CC=CC(F)=C5)O1)=O

InChI

1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35)

InChI key

BCFGMOOMADDAQU-UHFFFAOYSA-N

Gene Information

human ... EGFR(1956) , ERBB2(2064)

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Biochem/physiol Actions

Lapatinib acts as a dual tyrosine kinase inhibitor of epidermal growth factor receptor (EGFR/ErbB1) and human epidermal growth factor receptor 2 (HER2/ErbB2). It competes for its binding site on the tyrosine kinase domain with adenosine triphosphate (ATP). Lapatinib mediates has been studied in vitro in the inhibition of cell growth as well as and apoptosis induction in several human cancer cells such as breast, lung, vulva, gastric, and head and neck cancer.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319,H362,H413

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Lact.

Storage Class Code

11 - Combustible Solids

WGK

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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Lapatinib in breast cancer
Bilancia D, et al.
Annals of Oncology, 18, vi26-vi30 (2007)
Dongwei Zhang et al.
Molecular cancer therapeutics, 7(7), 1846-1850 (2008-07-23)
Epidermal growth factor receptor (EGFR/ErbB1) and HER2 (ErbB2/neu), members of the ErbB receptor tyrosine kinase family, are frequently overexpressed in breast cancer and are known to drive tumor growth and progression, making them promising targets for cancer therapy. Lapatinib is
Sharad Verma et al.
PloS one, 13(2), e0190942-e0190942 (2018-02-02)
HER-2 belongs to the human epidermal growth factor receptor (HER) family. Via different signal transduction pathways, HER-2 regulates normal cell proliferation, survival, and differentiation. Recently, it was reported that MCF10A, BT474, and MDA-MB-231 cells bearing the HER2 K753E mutation were
Egle Avizienyte et al.
The Biochemical journal, 415(2), 197-206 (2008-07-01)
Recent clinical data indicates that the emergence of mutant drug-resistant kinase alleles may be particularly relevant for targeted kinase inhibitors. In order to explore how different classes of targeted therapies impact upon resistance mutations, we performed EGFR (epidermal-growth-factor receptor) resistance
Richard M Tehan et al.
Journal of natural products, 85(5), 1363-1373 (2022-05-03)
The genome of entomopathogenic fungus Tolypocladium inflatum Gams encodes 43 putative biosynthetic gene clusters for specialized metabolites, although genotype-phenotype linkages have been reported only for the cyclosporins and fumonisins. T. inflatum was cultured in defined minimal media, supplemented with or
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