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US Patents

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Health Canada Patents

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Chemistry

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Also known as: 1194506-26-7, Hmpl-013, Hmpl013, Fruquintinib [who-dd], Fruquintinib(hmpl-013), 6-(6,7-dimethoxyquinazolin-4-yl)oxy-n,2-dimethyl-1-benzofuran-3-carboxamide

Molecular Formula

C₂₁H₁₉N₃O₅

Molecular Weight

393.4 g/mol

InChI Key

BALLNEJQLSTPIO-UHFFFAOYSA-N

FDA UNII

49DXG3M5ZW

Fruquintinib is an orally available, small molecule inhibitor of vascular endothelial growth factor receptors (VEGFRs), with potential anti-angiogenic and antineoplastic activities. Upon oral administration, fruquintinib inhibits VEGF-induced phosphorylation of VEGFRs 1, 2, and 3 which may result in the inhibition of migration, proliferation and survival of endothelial cells, microvessel formation, the inhibition of tumor cell proliferation, and tumor cell death. Expression of VEGFRs may be upregulated in a variety of tumor cell types.

1 2D Structure

Fruquintinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-(6,7-dimethoxyquinazolin-4-yl)oxy-N,2-dimethyl-1-benzofuran-3-carboxamide

2.1.2 InChI

InChI=1S/C21H19N3O5/c1-11-19(20(25)22-2)13-6-5-12(7-16(13)28-11)29-21-14-8-17(26-3)18(27-4)9-15(14)23-10-24-21/h5-10H,1-4H3,(H,22,25)

2.1.3 InChI Key

BALLNEJQLSTPIO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C2=C(O1)C=C(C=C2)OC3=NC=NC4=CC(=C(C=C43)OC)OC)C(=O)NC

2.2 Other Identifiers

2.2.1 UNII

49DXG3M5ZW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hmpl-013

2.3.2 Depositor-Supplied Synonyms

1. 1194506-26-7

2. Hmpl-013

3. Hmpl013

4. Fruquintinib [who-dd]

5. Fruquintinib(hmpl-013)

6. 6-(6,7-dimethoxyquinazolin-4-yl)oxy-n,2-dimethyl-1-benzofuran-3-carboxamide

7. Fruquintinib [usan]

8. 49dxg3m5zw

9. 6-(6,7-dimethoxyquinazolin-4-yloxy)-n,2-dimethylbenzofuran-3-carboxamide

10. 3-benzofurancarboxamide, 6-((6,7-dimethoxy-4-quinazolinyl)oxy)-n,2-dimethyl-

11. 6-[(6,7-dimethoxyquinazolin-4-yl)oxy]-n,2-dimethyl-1-benzofuran-3-carboxamide

12. 6-((6,7-dimethoxyquinazolin-4-yl)oxy)-n,2-dimethylbenzofuran-3-carboxamide

13. Unii-49dxg3m5zw

14. Elunate

15. Fruquintinib [inn]

16. Fruquintinib; Hmpl-013

17. Fruquintinib (hmpl-013)

18. Schembl947183

19. Gtpl9428

20. Hmpl 013

21. Chembl4303214

22. Bcp15692

23. Ex-a2262

24. Nsc801000

25. Nsc829498

26. S5667

27. Who 10348

28. 6-[(6,7-dimethoxy-4-quinazolinyl)oxy]-n,2-dimethyl-3-benzofurancarboxamide

29. Akos026750586

30. Zinc114898570

31. Ccg-268573

32. Cs-5558

33. Db11679

34. Nsc-801000

35. Nsc-829498

36. Sb17123

37. Ncgc00481603-01

38. As-73141

39. Hmpl-013;hmpl013;hmpl 013

40. Hy-19912

41. B5864

42. A14393

43. C71641

44. A898991

45. Q27259271

46. B2693-470819

2.4 Create Date

2009-12-15

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₉N₃O₅
Molecular Weight	393.4 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	393.13247072 g/mol
Monoisotopic Mass	393.13247072 g/mol
Topological Polar Surface Area	95.7 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	579
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