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Also known as: Avitinib, 1557267-42-1, Ac0010, N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)phenyl)acrylamide, Ex-acea0010, Abivertinib [usan]

Molecular Formula

C₂₆H₂₆FN₇O₂

Molecular Weight

487.5 g/mol

InChI Key

UOFYSRZSLXWIQB-UHFFFAOYSA-N

FDA UNII

CER0OPG92L

Abivertinib is an orally available, irreversible, epidermal growth factor receptor (EGFR) mutant-selective inhibitor, with potential antineoplastic activity. Upon oral administration, abivertinib covalently binds to and inhibits the activity of mutant forms of EGFR, including the drug-resistant T790M EGFR mutant, which prevents signaling mediated by mutant forms of EGFR. This may both induce cell death and inhibit tumor growth in EGFR-mutated tumor cells. EGFR, a receptor tyrosine kinase that is mutated in a variety of cancers, plays a key role in tumor cell proliferation and tumor vascularization. As this agent is selective towards mutant forms of EGFR, its toxicity profile may be reduced when compared to non-selective EGFR inhibitors, which also inhibit wild-type EGFR.

1 2D Structure

Abivertinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide

2.1.2 InChI

InChI=1S/C26H26FN7O2/c1-3-23(35)29-17-5-4-6-19(15-17)36-25-20-9-10-28-24(20)31-26(32-25)30-18-7-8-22(21(27)16-18)34-13-11-33(2)12-14-34/h3-10,15-16H,1,11-14H2,2H3,(H,29,35)(H2,28,30,31,32)

2.1.3 InChI Key

UOFYSRZSLXWIQB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)C2=C(C=C(C=C2)NC3=NC4=C(C=CN4)C(=N3)OC5=CC=CC(=C5)NC(=O)C=C)F

2.2 Other Identifiers

2.2.1 UNII

CER0OPG92L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-propenamide, N-(3-((2-((3-fluoro-4-(4-methyl-1-piperazinyl)phenyl)amino)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)-

2. 2-propenamide, N-(3-((2-((3-fluoro-4-(4-methyl-1-piperazinyl)phenyl)amino)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)-, (2z)-2-butenedioate (1:1)

3. 2-propenamide, N-(3-((2-((3-fluoro-4-(4-methyl-1-piperazinyl)phenyl)amino)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)-, (2z)-2-butenedioate, Hydrate (1:1:2)

4. A-610ma

5. A610ma

6. Abivertinib Maleate

7. Abivertinib Maleate Anhydrous

8. Abivertinib Maleate Dihydrate

9. Ac-0010

10. Ac-0010 Maleate Dihydrate

11. Ac-0010ma

12. Ac0010

13. Ac0010ma

14. Acea100610

15. Avitinib

16. Avitinib Maleate

17. Ex-acea0010

18. Ex-acea0010ma

19. Exacea0010ma

20. Fujovee

21. N-(3-((2-((3-fluoro-4-(4-methyl-1-piperazinyl)phenyl)amino)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)acrylamide

22. Sti-5656

23. Sti5656

2.3.2 Depositor-Supplied Synonyms

1. Avitinib

2. 1557267-42-1

3. Ac0010

4. N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)phenyl)acrylamide

5. Ex-acea0010

6. Abivertinib [usan]

7. Acea100610

8. Cer0opg92l

9. Ac-0010

10. A610

11. Abivertinib (usan)

12. 1557267-42-1 (free Base)

13. N-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide

14. 2-propenamide, N-(3-((2-((3-fluoro-4-(4-methyl-1-piperazinyl)phenyl)amino)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)-

15. 2-propenamide, N-[3-[[2-[[3-fluoro-4-(4-methyl-1-piperazinyl)phenyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]-

16. N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenyl)prop-2-enamide

17. N-(3-{2-[3-fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7h-pyrrolo[2,3-d]pyrimidin-4-yloxy-phenyl)-acrylamide

18. Avitinib Free Base

19. Fujovee

20. Avitinib (ac0010)

21. Unii-cer0opg92l

22. Abivertinib [inn]

23. Avitinib (superceded Inn)

24. Avitinib [who-dd]

25. Abivertinib [who-dd]

26. Chembl4297865

27. Schembl15453394

28. Gtpl10044

29. Ex-a783

30. Bdbm294480

31. Avitinib(ac0010/ac0010ma)

32. Bcp16381

33. Us9586965, Cpd 3

34. Mfcd29089376

35. S8741

36. Zinc142081723

37. Ac 0010

38. Cs-w008904

39. Db15327

40. Ac-35320

41. Ds-19269

42. Hy-19816

43. N-(3-{2-[3-fluoro-4-(4-methyl-piperazin-1-yl)-phenylamino]-7h-pyrrolo[2,3-d]pyrimidin-4-yloxy}-phenyl)-acrylamide

44. Cs-0016789

45. A16826

46. D11308

47. F17427

48. A927386

49. N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1- Yl)phenyl)amino)-7h-pyrrolo[2,3-d]- Pyrimidin-4-yl)oxy)phenyl)acrylamide

50. N-(3-(2-(3-fluoro-4-(4-methylpiperazin-1-yl)phenylamino)-7h-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl)acrylamide

51. N-[3-[[2-[[3-fluoro-4-(4-methyl-1-piperazinyl)phenyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]-2-propenamide

2.4 Create Date

2014-02-18

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₆FN₇O₂
Molecular Weight	487.5 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	487.21320126 g/mol
Monoisotopic Mass	487.21320126 g/mol
Topological Polar Surface Area	98.4 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	752
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Protein Kinase Inhibitors

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

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