WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 120204
CAS#: 850140-73-7 (dimaleate)
Description: Afatinib dimaleate is an orally bioavailable dual receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. EGFR/HER2 tyrosine kinase inhibitor BIBW 2992 irreversibly binds to and inhibits human epidermal growth factor receptors 1 and 2 (EGFR-1; HER2), which may result in the inhibition of tumor growth and angiogenesis. EGFR/HER2 are RTKs that belong to the EGFR superfamily; both play major roles in tumor cell proliferation and tumor vascularization and are overexpressed in many cancer cell types. Afatinib is approved in much of the world (including the United States, Canada, the United Kingdom and Australia) for the treatment of metastatic non-small cell lung carcinoma (NSCLC), developed by Boehringer Ingelheim. It acts as an angiokinase inhibitor.
MedKoo Cat#: 120204
Name: Afatinib dimaleate
CAS#: 850140-73-7 (dimaleate)
Chemical Formula: C32H33ClFN5O11
Exact Mass:
Molecular Weight: 718.09
Elemental Analysis: C, 53.52; H, 4.63; Cl, 4.94; F, 2.65; N, 9.75; O, 24.51
Related CAS #: 850140-73-7 (dimaleate) 439081-18-2 (free base) 850140-72-6 (free base)
Synonym: BIBW-2992; BIBW 2992; BIBW2992. Afatinib dimaleate; trade name: Gilotrif, Tomtovok and Tovok.
IUPAC/Chemical Name: (S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide dimaleate
InChi Key: USNRYVNRPYXCSP-JUGPPOIOSA-N
InChi Code: InChI=1S/C24H25ClFN5O3.2C4H4O4/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15;2*5-3(6)1-2-4(7)8/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29);2*1-2H,(H,5,6)(H,7,8)/b4-3+;2*2-1-/t16-;;/m0../s1
SMILES Code: O=C(NC1=CC2=C(NC3=CC=C(F)C(Cl)=C3)N=CN=C2C=C1O[C@@H]4COCC4)/C=C/CN(C)C.O=C(O)/C=C\C(O)=O.O=C(O)/C=C\C(O)=O
Appearance: White to off-white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: 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 Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 718.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Prim N, Fore M, Mennecier B. [Afatinib (BIBW 2992).]. Rev Pneumol Clin. 2014 May 27. pii: S0761-8417(14)00047-9. doi: 10.1016/j.pneumo.2014.03.002. [Epub ahead of print] Review. French. PubMed PMID: 24878189.
2: D'Arcangelo M, Hirsch FR. Clinical and comparative utility of afatinib in non-small cell lung cancer. Biologics. 2014 Apr 23;8:183-92. doi: 10.2147/BTT.S40567. eCollection 2014. Review. PubMed PMID: 24790411; PubMed Central PMCID: PMC4003149.
3: Bowles DW, Weickhardt A, Jimeno A. Afatinib for the treatment of patients with EGFR-positive non-small cell lung cancer. Drugs Today (Barc). 2013 Sep;49(9):523-35. doi: 10.1358/dot.2013.49.9.2016610. Review. PubMed PMID: 24086949.
4: Köhler J, Schuler M. Afatinib, erlotinib and gefitinib in the first-line therapy of EGFR mutation-positive lung adenocarcinoma: a review. Onkologie. 2013;36(9):510-8. doi: 10.1159/000354627. Epub 2013 Aug 19. Review. PubMed PMID: 24051929.
5: Yap TA, Popat S. The role of afatinib in the management of non-small cell lung carcinoma. Expert Opin Drug Metab Toxicol. 2013 Nov;9(11):1529-39. doi: 10.1517/17425255.2013.832755. Epub 2013 Aug 28. Review. PubMed PMID: 23985030.
6: Dungo RT, Keating GM. Afatinib: first global approval. Drugs. 2013 Sep;73(13):1503-15. doi: 10.1007/s40265-013-0111-6. Review. PubMed PMID: 23982599.
7: Chen X, Zhu Q, Zhu L, Pei D, Liu Y, Yin Y, Schuler M, Shu Y. Clinical perspective of afatinib in non-small cell lung cancer. Lung Cancer. 2013 Aug;81(2):155-61. doi: 10.1016/j.lungcan.2013.02.021. Epub 2013 May 10. Review. PubMed PMID: 23664448.
8: Yang JC, Reguart N, Barinoff J, Köhler J, Uttenreuther-Fischer M, Stammberger U, O'Brien D, Wolf J, Cohen EE. Diarrhea associated with afatinib: an oral ErbB family blocker. Expert Rev Anticancer Ther. 2013 Jun;13(6):729-36. doi: 10.1586/era.13.31. Epub 2013 Mar 18. Review. PubMed PMID: 23506556.
9: Lacouture ME, Schadendorf D, Chu CY, Uttenreuther-Fischer M, Stammberger U, O'Brien D, Hauschild A. Dermatologic adverse events associated with afatinib: an oral ErbB family blocker. Expert Rev Anticancer Ther. 2013 Jun;13(6):721-8. doi: 10.1586/era.13.30. Epub 2013 Mar 18. Review. PubMed PMID: 23506519.
10: Geuna E, Montemurro F, Aglietta M, Valabrega G. Potential of afatinib in the treatment of patients with HER2-positive breast cancer. Breast Cancer (Dove Med Press). 2012 Aug 27;4:131-7. doi: 10.2147/BCTT.S25868. Review. PubMed PMID: 24367201; PubMed Central PMCID: PMC3846413.
Related CAS#
850140-73-7 (Afatinib dimaleate)
439081-18-2 (Afatinib free base).
