Cat. No. Name Size Price Add Cart
KI0068BIBW29925 mg$80
BIBW299210 mg$113.4
BIBW299250 mg$372.6
BIBW2992200 mg$1039.5

Chemical Characteristic

Product NameBIBW2992
SynonymsAfatinib
CAS No.439081-18-2
Molecular Weight 485.94
FormulaC24H25ClFN5O3
Chemical Name(S,E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
SmilesC(=O)(/C=C/CN(C)C)Nc1cc2c(ncnc2cc1OC1COCC1)Nc1cc(c(cc1)F)Cl
Chemical Structure
DocumentsHPLC MS COA

Biological activities

BIBW2992 is an irreversible inhibitor of ErbB family with IC50s of 0.5, 14 and 1 nM for epidermal growth factor receptor (EGFR) (ErbB1/HER1), HER2 and HER4 kinases. BIBW2992 inhibits EGF-induced EGFR phosphorylation and cellular proliferation in cell lines such as EGFR-overexpressing and HER2-expressing cell lines A431, NIH-3T3-HER2, NCI-N87 and BT-474. [1] In cell-free in vitro kinase assays, BIBW2992 also demonstrates potent activity against mutant forms of EGFR and HER2. In three NSCLC cell lines (H1666, H3255 and H1975), BIBW2992 potently inhibits EGFR phosphorylation in all three cell lines with IC50s of 7, 6 and 93 nM, respectively. Furthermore, BIBW2992 is shown to be more effective than erlotinib, gefitinib or lapatinib in inhibiting survival of lung cancer cell lines. [2] BIBW2992 also shows great activity in human pancreatic tumour cells. Of the seven human pancreatic tumor cell lines including Capan-1, PT-45, PANC-1, BxPC-3, MiaPaCa-2, AsPc-1, FA6 examined, BxPC-3 cells are the most sensitive cell line to treatment with BIBW2992 with an IC50 of 11 nM, and the growth of other human pancreatic tumor cells is inhibited by BIBW2992 with IC50s ranging from 0.37 to 1.37 µM.[3] Meanwhile, BIBW2992 is similar to gefitinib in potency for L858R EGFR with an IC50 of 0.7 nM, but approximately 100-fold more active against the gefitinib-resistant L858R/T790M EGFR double mutant with an IC50 of 99 nM. BIBW2992 suppresses transformation in isogenic cell-based assays, inhibits survival of cancer cell lines and induces tumor regression in xenograft and transgenic lung cancer models, with superior activity over erlotinib.[4] Oral BIBW2992 induces tumour regression in mice carrying EGFR-overexpressing and HER2-expressing A431 xenografts, in mice carrying EGFR-over-expressing and HER2-expressing MDA-MB-453 xenografts, and in NCI-N87 gastric and SKOV-3 ovarian models at plasma concentrations of 80-280 nM.[1] In vivo , BIBW2992 shows potent anti-tumour activity in the BxPC-3 human pancreatic xenograft model. Daily administration of 15 mg/kg BIBW2992 as a single agent to mice carrying established tumours significantly delays tumour growth with a T/C value of 18% and a tumour growth inhibition (TGI) value of 89%.[3]

Protocols

BIBW2992 is prepared in DMSO. [3]

References

[1] Eskens FA, et al. A phase I dose escalation study of BIBW 2992, an irreversible dual inhibitor of epidermal growth factor receptor 1 (EGFR) and 2 (HER2) tyrosine kinase in a 2-week on, 2-week off schedule in patients with advanced solid tumours. Br J Cancer. 2008, 98(1): 80-85.
[2] Hirsh V, et al. Afatinib (BIBW 2992) development in non-small-cell lung cancer. Future Oncol. 2011, 7(7): 817-825.
[3] Ioannou N, et al. Anti-tumour activity of afatinib, an irreversible ErbB family blocker, in human pancreatic tumour cells. Br J Cancer. 2011, 105(10): 1554-1562.
[4] Bordoni RE, et al. Afatinib (BIBW 2992): a novel dual EGFR/HER2neu inhibitor with promising activity in non-small-cell lung cancer. Therapy. 2011, 8 (1): 15-22.

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