Afatinib dimaleate

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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.

Price and Availability

Afatinib dimaleate, purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 120204Name: Afatinib dimaleateCAS#: 850140-73-7 (dimaleate)Chemical Formula: C32H33ClFN5O11Exact Mass: Molecular Weight: 718.09Elemental 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=CC(O)=O.O=C(O)/C=CC(O)=O

Technical Data

Additional Information

Related CAS#850140-73-7 (Afatinib dimaleate) 439081-18-2 (Afatinib free base).

References

1: Prim N, Fore M, Mennecier B. [Afatinib (BIBW2992).]. 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 ofafatinib 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 ofpatients 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 thefirst-line therapy of EGFR mutation-positive lung adenocarcinoma: areview. Onkologie. 2013;36(9):510-8. doi: 10.1159/000354627. Epub 2013Aug 19. Review. PubMed PMID: 24051929.

5: Yap TA, Popat S. The role of afatinib in the management of non-smallcell lung carcinoma. Expert Opin Drug Metab Toxicol. 2013Nov;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. 2013Sep;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. Clinicalperspective of afatinib in non-small cell lung cancer. Lung Cancer. 2013Aug;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 withafatinib: an oral ErbB family blocker. Expert Rev Anticancer Ther. 2013Jun;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 eventsassociated with afatinib: an oral ErbB family blocker. Expert RevAnticancer Ther. 2013 Jun;13(6):721-8. doi: 10.1586/era.13.30. Epub 2013Mar 18. Review. PubMed PMID: 23506519.

10: Geuna E, Montemurro F, Aglietta M, Valabrega G. Potential ofafatinib 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 CentralPMCID: PMC3846413.