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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

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 Formula	C₃₂H₃₃ClFN₅O₁₁
Molecular Weight	718.1 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	12
Exact Mass	717.1849127 g/mol
Monoisotopic Mass	717.1849127 g/mol
Topological Polar Surface Area	238 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	821
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

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

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