| Identification | Back Directory | [Name]
Lapatinib Ditosylate | [CAS]
388082-77-7 | [Synonyms]
GW-572016F
Tykerb Ditosylat
Tykerb Ditosylate
Tykerb(lapatinib)
GW 572016 ditosylate
GW-572016 ditosylate
Lapatinib ditasylate
Lapatinib ditosylate
GW-572016F Ditosylate
Lapatinib Ditosylate (Tykerb)
Lapatinib (GW-572016) Ditosylate
N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-6-(5-((2-(methylsulfonyl)ethylamino)methyl)furan-2-yl)quinazolin-4-amine,di4-methylbenzenesulfonate
N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(Methylsulfonyl)ethyl]aMino}Methyl)-2-furyl]-4-quinazolinaMine 4-Methylbenzenesulfonate (1:2)
N-(3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(Methylsulfonyl)ethyl)aMino)Methyl)furan-2-yl)quinazolin-4-aMine bis(4-Methylbenzenesulfonate)
N-{3-chloro-4-[(3-fluorobenzyl)oxyl]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)furan-2-yl]quinazolin-4-amine bis(4-methylBenzenesulfonate)
4-QuinazolinaMine, N-[3-chloro-4-[(3-fluorophenyl)Methoxy]phenyl]-6-[5-[[[2-(Methylsulfonyl)ethyl]aMino]Methyl]-2-furanyl]-, 4-Methylbenzenesulfonate (1:2)
N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[[[2-(methylsulfonyl)ethyl]amino]methyl]-2-furanyl]-4-quinazolinamine Bis(4-methylbenzenesulfonate) Ditosylate | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C43H42ClFN4O10S3 | [MDL Number]
MFCD09264195 | [MOL File]
388082-77-7.mol | [Molecular Weight]
925.46 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [Melting point ]
240-2420C | [storage temp. ]
-20°C Freezer, Under Inert Atmosphere | [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 |
| Hazard Information | Back Directory | [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]
Reversible dual inhibitor of ErbB1 and ErbB2 tyrosine kinases. Antineoplastic | [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. | [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]
Lapatinib (GW2016; 30-100 mg/kg; oral administration; twice daily; for 21 days; CD-1 nude female mice) treatment inhibits tumor xenograft growth of the HN5 cells in a dose-responsive manner at 30 and 100 mg/kg, with complete inhibition of tumor growth at the higher dose[1]. | Animal Model: | CD-1 nude female mice (4-6 weeks old) with HN5 cells[1] | | Dosage: | 30 mg/kg, 100 mg/kg | | Administration: | Oral administration; twice daily; for 21 days | | Result: | Inhibited tumor xenograft growth of the HN5 cells in a dose-responsive manner.
|
| [IC 50]
EGFR: 10.8 nM (IC50, Cell Free Assay); ErbB2: 9.2 nM (IC50, Cell Free Assay) | [storage]
Store at -20°C |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
NCE Biomedical Co.,Ltd.
|
| Telephone: |
4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList15748/0_EN.htm |
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