Lapatinib, EGFR and HER2 tyrosine kinase inhibitor

Key facts

CAS number

231277-92-2

Purity

>98%

Form

Solid

form

Molecular weight

581.1 Da

Molecular formula

C₂₉H₂₆ClFN₄O₄S

PubChem

208908

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Biochemical name

Lapatinib

Biological description

Cell-permeable, potent dual tyrosine kinase inhibitor of EGFR and HER2 (ERBB2) (IC₅₀ values are 3 nM and 13 nM respectively). Also inhibits HER4 (IC₅₀ = 347 nM). Reduces tyrosine phosphorylation of EGFR and HER2, and inhibits activation of Erk1/2 and AKT, downstream effectors of proliferation and cell survival, respectively. Inhibits tumor cell growth in vitro and in xenograft models for a variety of human tumors. Effective in vivo and is used in combination therapy to prevent or suppress cancers where these kinases are over-​expressed, including breast cancer.

Canonical smiles

CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl

InChi

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)

InChiKey

BCFGMOOMADDAQU-UHFFFAOYSA-N

IUPAC Name

N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine