BIBW2992 (Afatinib) is an orally-available, aminoquinazoline-acrylamide-based inhibitor with IC50 potency for EGFRwt, EGFR(L858R), EGFR(L858R/T790M), and HER2 at 0.5, 0.4, 10, and 14 nM, respectively. [1] Via its crotonamide functional group, BIBW2992 targets the ErbB family in an irreversible manner, providing a sustained, selective, and covalent inhibition that has been shown to be effective toward erlotinib-resistant tumors. [2]
In cellular assays, BIBW2992 inhibits phosphorylation of EGFR wild type (A431), EGFR (NCI-H1975), and HER2 (BT474) at EC50s of 8, 49, and 75 nM, respectively. [3]
BIBW2992 displays potent growth inhibition of EGFR/HER2 expressing lung cancer cell lines H1666, H3255, and NCI1975 at IC50 values of 60, 0.7, and 99 nM, respectively. [1]
Technical information:
| Chemical Formula: | C24H25ClFN5O3 | |
| CAS #: | 439081-18-2 | |
| Molecular Weight: | 485.94 | |
| Purity: | > 98% | |
| Appearance: | Off White | |
| Chemical Name: | (S,E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide | |
| Solubility: | Up to 100 mM in DMSO | |
| Synonyms: | BIBW2992, BIBW-2992, Afatinib, Tovok, Tomtovok |
Shipping Condition: The product is shipped in a glass vial at ambient temperature.
Storage condition: For longer shelf life, store solid powder at 4oC desiccated, or store DMSO solution at -20oC.
Reference:
| 1. | Li et al., BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models. Oncogene, 2008, 27(34), 4702-4711. Pubmed ID: 18408761 |
| 2. | Boehringer Ingelheim backgrounder (BIBW2992, Afatinib), May, 2012. |
| 3. | Solca et al., Target binding properties and cellular activity of afatinib (BIBW 2992), an irreversible ErbB family blocker. J. Pharmacol. Exp. Ther. 2012, 343(2), 342-350. Pubmed ID: 22888144 |
Other Information:
Product Specification (pdf)
MSDS (pdf)
Certificate of Analysis is available upon request.
