Lapatinib Ditosylate Chemical Properties

Melting point:

240-2420C

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

≥24.3 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O

form 

solid

color 

Light yellow to yellow

Water Solubility 

Water: Insoluble

CAS DataBase Reference

388082-77-7

Safety Information

Safety Statements 

24/25

HS Code 

29420000

Lapatinib Ditosylate Usage And Synthesis

Description

Lapatinib, an ErB-1 and ErB-2 dual kinase inhibitor, was launched for the treatment of advanced or metastatic HER2 (ErbB2) positive breast cancer in women who have received prior therapy. The drug was discovered and developed by GlaxoSmithKline and is also currently being evaluated for several additional cancer indications.

Chemical Properties

Yellow Solid

Uses

Lapatinib Ditosylate (GW572016, GW2016, Tykerb, Tyverb) is a potent EGFR and ErbB2 inhibitor with IC50 of 10.8 and 9.2 nM, respectively.

Uses

Lapatinib Ditosylate is a reversible dual inhibitor of ErbB1 and ErbB2 tyrosine kinases. Antineoplastic.

Synthesis

The synthesis started with Williamson ether synthesis between 2-chloro-4-nitrophenol (58) and 3-fluorobenzyl bromide to give ether 59 in the following scheme; however, no specific yields were provided. Reduction of the nitro group of compound 59 by catalytic hydrogenation over Pt/C and subsequent condensation of the resulting aniline with 4-chloro-6-iodoquinazoline (61) in refluxing i-PrOH afforded compound 62. 4-Chloro-6-iodoquinazoline (61) was prepared by reacting 6-iodoquinazolin- 4(3H)-one (60) with POCl3 in the presence of triethylamine. Compound 62 was subjected to Stille coupling with 5- dioxolanyl-2-(tributylstannyl)furan (63) in the presence of PdCl2(PPh3)2 to give 64. Acidic hydrolysis of acetal 64 using HCl in THF/H2O provided the corresponding aldehyde which was further subjected to reductive amination with 2-(methan-esulfonyl)ethylamine in the presence of sodium triacetoxyborohydride to yield lapatinib. Lapatinib was treated with ptoluenesulfonic acid solution to give lapatinib ditosylate (IX).

in vivo

IC 50

EGFR: 10.8 nM (IC₅₀, Cell Free Assay); ErbB2: 9.2 nM (IC₅₀, Cell Free Assay)

Lapatinib Ditosylate(388082-77-7)Related Product Information

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