Afatinib free base · Synonyms: BIBW 2992 | Gilotrif | Tovok

Afatinib is an orally active, potent and irreversible dual specificity inhibitor of ErbB family.

For research use only. Not for human or veterinary use.

Target EGFR Autophagy Apoptosisc-Met/HGFR Akt p38 MAPK

Research area Cancer

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Data Sheet SDS COA

Afatinib structure

CAS No.: 850140-72-6

Download structure (.mol)

Pack sizes & pricing

Size	Price	SKU	Stock
500 mg	USD 320.00	BP-02089-500mg	In stock	Get quote
1 g	USD 512.00	BP-02089-1g	In stock	Get quote
2 g	USD 820.00	BP-02089-2g	In stock	Get quote
3 g	USD 980.00	BP-02089-3g	In stock	Get quote
5 g	USD 1,310.00	BP-02089-5g	In stock	Get quote
10 g	USD 2,100.00	BP-02089-10g	In stock	Get quote

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Related forms

BP-02089A — Afatinib dimaleate

Description

Afatinib (BIBW 2992) is an orally active, potent and irreversible dual specificity inhibitor of ErbB family (EGFR and HER2), with IC50 values of 0.5 nM, 0.4 nM, 10 nM and 14 nM for EGFRwt, EGFRL858R, EGFRL858R/T790M and HER2, respectively.

Biological activity

In Vitro Afatinib (100 nM) sufficiently prevents heregulin-stimulated HER3 phosphorylation. Afatinib (0-10000 nM) effectively inhibits anchorage-independent proliferation of NIH-3T3 cells ectopically expressing EGFR mutants, and inhibits cell proliferation of H1666, H3255, and NCI 1975 cells. Afatinib (48-72 h)shows growth inhibition in HKESC-1, HKESC-2, SLMT-1 and EC-1 cells. Afatinib (0-1 μM, 24-48 h) inhibits AKT and MAPK pathways, and inhibits EGFR and AKT phosphorylation in ESCC cell lines. Afatinib (0-1 μM, 16-48 h) induces G0/G1 cell cycle arrest in HKESC-2 and EC-1. Afatinib (0-1 μM, 24-48 h) effectively induces apoptotic cell death in HKESC-2 and EC-1. In Vivo Afatinib (0-20 mg/kg, Orally, daily for 25 days) shows dramatic tumor regression and downregulation of EGFR, HER2, HER3 and AKT phosphorylation. Afatinib (15 mg/kg, Orally, in a schedule of 5 days on plus 2 days off, for two weeks) strongly inhibits the growth of HKESC-2 tumor.

Identifiers

SMILES: N(C=1C2=C(C=C(O[C@H]3CCOC3)C(NC(/C=C/CN(C)C)=O)=C2)N=CN1)C4=CC(Cl)=C(F)C=C4
InChIKey: ULXXDDBFHOBEHA-CWDCEQMOSA-N

Specifications

MW (average): 485.9380
Formula: C₂₄H₂₅ClFN₅O₃
CAS No.: 850140-72-6
Physical state: Solid
Color: white to yellow
Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage: Powder -20°C, 3 years , 4°C, 2 years ; In solvent -20°C, 1 month

Solubility

Soluble in DMSO : 100 mg/mL

Documents

References

[1]. Li D, et al. BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models. Oncogene. 2008 Aug 7;27(34):4702-11.

[2]. Wong CH, et al. Preclinical evaluation of afatinib (BIBW2992) in esophageal squamous cell carcinoma (ESCC). Am J Cancer Res. 2015 Nov 15;5(12):3588-99.

[3]. Wang XK, et al. Afatinib circumvents multidrug resistance via dually inhibiting ATP binding cassette subfamily G member 2 in vitro and in vivo. Oncotarget. 2014 Dec 15;5(23):11971-85.

[4]. Yoshioka T, et al. Antitumor activity of pan-HER inhibitors in HER2-positive gastric cancer. Cancer Sci. 2018 Apr;109(4):1166-1176.

Same target

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Same research area

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