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    Chemistry

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    Also known as: 850140-73-7, Afatinib (dimaleate), Gilotrif, Afatinib maleate, Bibw 2992ma2, Giotrif
    Molecular Formula
    C32H33ClFN5O11
    Molecular Weight
    718.1  g/mol
    InChI Key
    USNRYVNRPYXCSP-JUGPPOIOSA-N
    FDA UNII
    V1T5K7RZ0B
    Afatinib
    A quinazoline and butenamide derivative that acts as a tyrosine kinase inhibitor of epidermal growth factor receptors (ERBB RECEPTORS) and is used in the treatment of metastatic NON-SMALL CELL LUNG CANCER.
    1 2D Structure

    Afatinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (Z)-but-2-enedioic acid;(E)-N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide
    2.1.2 InChI
    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
    2.1.3 InChI Key
    USNRYVNRPYXCSP-JUGPPOIOSA-N
    2.1.4 Canonical SMILES
    CN(C)CC=CC(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)OC4CCOC4.C(=CC(=O)O)C(=O)O.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CN(C/C=C/C(=O)NC1=C(C=C2N=CN=C(C2=C1)NC3=CC(=C(C=C3)F)Cl)O[C@@H]4COCC4)C.C(=C\C(=O)O)\C(=O)O.C(=C\C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    V1T5K7RZ0B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2e)-n-(4-(3-chloro-4-fluoroanilino)-7-(((3s)-oxolan-3-yl)oxy)quinoxazolin-6-yl)-4-(dimethylamino)but-2-enamide

    2. Afatinib

    3. Afatinib Maleate

    4. Bibw 2992

    5. Bibw 2992 Ma2

    6. Bibw 2992ma2

    7. Bibw-2992

    8. Bibw-2992-ma2

    9. Bibw-2992ma2

    10. Bibw2992

    11. Bibw2992 Ma2

    12. Gilotrif

    2.3.2 Depositor-Supplied Synonyms

    1. 850140-73-7

    2. Afatinib (dimaleate)

    3. Gilotrif

    4. Afatinib Maleate

    5. Bibw 2992ma2

    6. Giotrif

    7. Afatinib (bibw2992) Dimaleate

    8. Afatinib Dimaleate [usan]

    9. Bibw2992 Ma2

    10. Afatinib Maleate (jan)

    11. V1t5k7rz0b

    12. Bibw-2992ma2

    13. Bibw2992-ma2

    14. Bibw-2992 Ma2

    15. Bibw-2992-ma2

    16. Chebi:76003

    17. 850140-73-7 (dimaleate)

    18. Bibw2992 Dimaleate

    19. Afatinib Dimaleate (usan)

    20. (s,e)-n-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide Dimaleate

    21. Afatinib Maleate [jan]

    22. Afatinib Impurity F

    23. (2e)-n-(4-((3-chloro-4-fluorophenyl)amino)-7-(((3s)-tetrahydrofuran-3-yl)oxy)quinazolin- 6-yl)-4-(dimethylamino)but-2-enamide Bis(hydrogen (2z)-but-2-enedioate)

    24. (z)-but-2-enedioic Acid;(e)-n-[4-(3-chloro-4-fluoroanilino)-7-[(3s)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide

    25. Unii-v1t5k7rz0b

    26. Mfcd25974239

    27. Gilotrif (tn)

    28. Giotrif (tn)

    29. Bibw2993 Dimaleate

    30. Amy499

    31. Afatinib Dimaleate [mi]

    32. Chembl2105712

    33. Afatinib Dimaleate [vandf]

    34. Dtxsid701027713

    35. Afatinib Dimaleate [who-dd]

    36. Hy-10261a

    37. S7810

    38. Akos025401819

    39. Ccg-270401

    40. Cs-1329

    41. Afatinib Dimaleate [orange Book]

    42. Ac-26080

    43. As-56967

    44. Ba162012

    45. D09733

    46. Q27145677

    47. (2e)-n-(4-[(3-chloro-4-fluorophenyl)amino]-7-{[(3s)-tetrahydrofuran-3-yl]oxy}quinazolin-6-yl)-4-(dimethylamino)but-2-enamide

    48. (2e)-n-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3s)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-butenamide Dimaleate

    49. (2e)-n-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3s)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide Di[(2z)-but-2-enedioate]

    50. (e)-4-dimethylamino-but-2-enoic Acid-(4-(3-chloro-4-fluoro-phenylamino)-7-((s)-tetra-hydrofuran-3-yloxy)-quinazolin-6yl)-amide Dimaleate

    51. 2-butenamide, N-(4-((3-chloro-4-fluorophenyl)amino)-7-(((3s)-tetrahydro-3-furanyl)oxy)- 6-quinazolinyl)-4-(dimethylamino)-, (2e)-, (2z)-2-butenedioate (1:2)

    52. 2-butenamide, N-(4-((3-chloro-4-fluorophenyl)amino)-7-(((3s)-tetrahydro-3-furanyl)oxy)-6-quinazolinyl)-4-(dimethylamino)-, (2e)-, (2z)-2-butenedioate (1:2)

    53. 936631-70-8

    2.4 Create Date
    2007-02-12
    3 Chemical and Physical Properties
    Molecular Weight 718.1 g/mol
    Molecular Formula C32H33ClFN5O11
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count12
    Exact Mass717.1849127 g/mol
    Monoisotopic Mass717.1849127 g/mol
    Topological Polar Surface Area238 Ų
    Heavy Atom Count50
    Formal Charge0
    Complexity821
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count3
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Indication

    Giotrif as monotherapy is indicated for the treatment of

    - Epidermal Growth Factor Receptor (EGFR) TKI-nave adult patients with locally advanced or metastatic non-small cell lung cancer (NSCLC) with activating EGFR mutation(s);

    - locally advanced or metastatic NSCLC of squamous histology progressing on or after platinum-based chemotherapy.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    5.2 ATC Code

    L01XE13

    API Reference Price

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