Lapatinib

Bezeichnung:Lapatinib

CAS-Nr231277-92-2

Englisch Name:Lapatinib

CBNumberCB8855402

SummenformelC29H26ClFN4O4S

Molgewicht581.06

MOL-Datei231277-92-2.mol

Lapatinib physikalisch-chemischer Eigenschaften

Schmelzpunkt	144-146oC
Siedepunkt	750.7±60.0 °C(Predicted)
Dichte	1.381±0.06 g/cm3(Predicted)
storage temp.	2-8°C(protect from light)
Löslichkeit	Soluble in DMSO (up to 200 mg/ml)
Aggregatzustand	solid
pka	6.34±0.19(Predicted)
Farbe	Yellow
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey	BCFGMOOMADDAQU-UHFFFAOYSA-N
SMILES	N1=C2C(C=C(C3=CC=C(CNCCS(C)(=O)=O)O3)C=C2)=C(NC2=CC=C(OCC3=CC=CC(F)=C3)C(Cl)=C2)N=C1
CAS Datenbank	231277-92-2(CAS DataBase Reference)

Sicherheit

HS Code	29349990
Giftige Stoffe Daten	231277-92-2(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Lapatinib Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Lapatinib, a new member of the 4-anilinoquinazoline class of RTK inhibitors (RTKIs), was launched as an oral treatment for breast cancer. Lapatinib has dual affinity for EGFR and HER2 tyrosine kinases. It is indicated in combination with capecitabine for treating patients with advanced or metastatic breast cancer whose tumors overexpress HER2 and who have received prior therapy including an anthracycline, a taxane, and trastuzumab. Previously marketed drugs from the 4-anilinoquinazoline class include erlotinib (Tarceva) and gefitinib (Iressa^TM), both of which are indicated for treating non-small-cell lung cancer (NSCLC). As with erlotinib and gefitinib, To Market, To Market 2007 475 lapatinib is an ATP-competitive kinase inhibitor. It inhibits the tyrosine kinase activity EGFR and HER-2 with apparent Ki values of 3 and 13 nM, respectively, and has slow off-rate kinetics (t1/2X300 min).
In addition, dividing the daily dose of lapatinib results in approximately 2-fold higher exposure at steady state compared to the same total dose administered once daily.
The chemical synthesis of lapatinib entails the condensation of 4-chloro-6-iodoquinazoline and 3-chloro-4-(3-fluorobenzyloxy)aniline to produce a diaryl amine intermediate followed by Stille coupling of the iodo group with 5-dioxolanyl-2-(tributylstannyl)furan and subsequent acid hydrolysis of the cyclic ketal to the corresponding aldehyde. Finally, reductive amination of the aldehyde intermediate with 2-(methanesulfonyl) ethylamine in the presence of sodium triacetoxyborohydride produces lapatinib. .
Originator
GSK (US)
Verwenden
Lapatinib, used in the form of Lapatinib Ditosylate, is a potent EGFR and ErbB2 inhibitor with IC50 of 10.8 and 9.2 nM, respectively. It is a antineoplastic which is used in breast cancer research and a tyrosine kinase inhibitor. It is used for the treatment of patients with advanced or metastatic breast cancer whose tumors overexpress HER2 (ErbB2)
Definition
ChEBI: Lapatinib is an organofluorine compound, an organochlorine compound, a member of quinazolines and a member of furans. It has a role as an antineoplastic agent and a tyrosine kinase inhibitor. It is functionally related to a monofluorobenzene.
Trademarks
Tykerb
Allgemeine Beschreibung
Class: receptor tyrosine kinase
Treatment: HER2-positive breast cancer
Elimination half-life = 24 h
Protein binding = 99%
target
EGFR
Lager
Store at -20°C
Einzelnachweise
1) Wood?et al. (2004),?A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells;? Cancer Res.,?64?6652 2) Burris?et al. (2004),?Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib;? Oncologist,?9?10 3) Chu?et al. (2005),?The dual ErbB1/ErbB2 inhibitor, lapatinib (GW572016) cooperates with tamoxifen to inhibit both cell proliferation- and estrogen-dependent gene expression in antiestrogen-resistant breast cancer;? Cancer Res.,?65?18

Lapatinib Upstream-Materialien And Downstream Produkte

Lapatinib Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

231277-92-2, Lapatinib Verwandte Suche:

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