Lapatinib Ditosylate
Lapatinib Ditosylate Basic information
- Product Name:
- Lapatinib Ditosylate
- Synonyms:
-
- TYKERB DITOSYLATE; GW 572016 DITOSYLATE; GW-572016 DITOSYLATE
- GW 572016 DITOSYLATE;GW-572016 DITOSYLATE
- Lapatinib ditosylate
- 4-QuinazolinaMine, N-[3-chloro-4-[(3-fluorophenyl)Methoxy]phenyl]-6-[5-[[[2-(Methylsulfonyl)ethyl]aMino]Methyl]-2-furanyl]-, 4-Methylbenzenesulfonate (1:2)
- Lapatinib Ditosylate (Tykerb)
- GW 572016 ditosylate
- GW-572016 ditosylate
- GW-572016F
- CAS:
- 388082-77-7
- MF:
- C36H34ClFN4O7S2
- MW:
- 753.26
- EINECS:
- 1312995-182-4
- Product Categories:
-
- Inhibitors
- Final material
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Tyrosine Kinase Inhibitors
- Mol File:
- 388082-77-7.mol
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).
Lapatinib DitosylateSupplier
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Lapatinib Ditosylate(388082-77-7)Related Product Information
- Lapatinib IMpurity 10
- Lapatinib
- Sorafenib tosylate
- Gefitinib
- Erlotinib hydrochloride
- Crizotinib
- Ruxolitinib
- Olaparib
- Lapatinib impurity L
- Lapatinib 2-Fluoro Impurity
- Lapatinib 4-Fluoro Impurity
- N-De[2-(Methylsulfonyl)ethyl] Lapatinib
- Lapatinib iMpurity
- Lapatinib Impurity 16
- 3-Chloro-4-(3-fluorobenzyloxy)aniline
- Lapatinib
- Lapatinib Ditosylate
- 2-AMINOETHANETHIOL P-TOLUENESULFONATE