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SML2259

Lapatinib

Name: Lapatinib
Brand: SIGMA

≥98% (HPLC), EGFR/ErbB1 and HER2/ErbB2 inhibitor, powder

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

NACRES:

NA.77

UNSPSC Code:

12352200

MDL number:

MFCD09264194

Assay:

≥98% (HPLC)

Form:

powder

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Product Name

Lapatinib, ≥98% (HPLC)

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

GHS07

signalword

Warning

hcodes

H319,H362,H413

pcodes

P201 - P260 - P263 - P273 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Lact.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Lapatinib in breast cancer

Bilancia D, et al.

Annals of Oncology, 18, vi26-vi30 (2007)

Activity of lapatinib is independent of EGFR expression level in HER2-overexpressing breast cancer cells.

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

Comparison of the EGFR resistance mutation profiles generated by EGFR-targeted tyrosine kinase inhibitors and the impact of drug combinations.

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

Tolypocladamide H and the Proposed Tolypocladamide NRPS in Tolypocladium Species.

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

Structural investigations on mechanism of lapatinib resistance caused by HER-2 mutants.

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

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Global Trade Item Number

SKU	GTIN
SML2259-10MG	04061835504930
SML2259-50MG	04061835504947

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