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Chemistry

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Also known as: 1000025-07-9, Akb-6548, Pg-1016548, Vadadustat [usan], N-(5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl)glycine, B506

Molecular Formula

C₁₄H₁₁ClN₂O₄

Molecular Weight

306.70 g/mol

InChI Key

JGRXMPYUTJLTKT-UHFFFAOYSA-N

FDA UNII

I60W9520VV

Vadadustat is an orally bioavailable, hypoxia-inducible factor prolyl hydroxylase (HIF-PH) inhibitor (HIF-PHI), with potential anti-anemic and anti-inflammatory activities. Upon administration, vadadustat binds to and inhibits HIF-PH, an enzyme responsible for the degradation of transcription factors in the HIF family under normal oxygen conditions. This prevents HIF breakdown and promotes HIF activity. Increased HIF activity leads to an increase in endogenous erythropoietin production, thereby enhancing erythropoiesis. It also reduces the expression of the peptide hormone hepcidin, improves iron availability, and boosts hemoglobin (Hb) levels. HIF regulates the expression of genes in response to reduced oxygen levels, including genes required for erythropoiesis and iron metabolism. In addition, HIF 1-alpha (HIF1A) may play a role in reducing inflammation during acute lung injury (ALI) through HIF-dependent control of glucose metabolism in the alveolar epithelium.

1 2D Structure

Vadadustat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid

2.1.2 InChI

InChI=1S/C14H11ClN2O4/c15-10-3-1-2-8(4-10)9-5-11(18)13(16-6-9)14(21)17-7-12(19)20/h1-6,18H,7H2,(H,17,21)(H,19,20)

2.1.3 InChI Key

JGRXMPYUTJLTKT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC(=C1)Cl)C2=CC(=C(N=C2)C(=O)NCC(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

I60W9520VV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Akb-6548

2.3.2 Depositor-Supplied Synonyms

1. 1000025-07-9

2. Akb-6548

3. Pg-1016548

4. Vadadustat [usan]

5. N-(5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl)glycine

6. B506

7. Pg1016548

8. B-506

9. Akb6548

10. (5-(3-chlorophenyl)-3-hydroxypicolinoyl)glycine

11. I60w9520vv

12. 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic Acid

13. Glycine, N-((5-(3-chlorophenyl)-3-hydroxy-2-pyridinyl)carbonyl)-

14. Glycine, N-[[5-(3-chlorophenyl)-3-hydroxy-2-pyridinyl]carbonyl]-

15. Vafseo

16. Glycine, N-[[5-(3-chlorophenyl)-3-hydroxy-2-pyridinyl]carbonyl]-;glycine, N-[[5-(3-chlorophenyl)-3-hydroxy-2-pyridinyl]carbonyl]-

17. Unii-i60w9520vv

18. Us8722895, 11: {[5-(3-chlorophenyl)-3-hydroxypyridine-2- Carbonyl]amino}-acetic Acid

19. A1z

20. Vafseo (tn)

21. Vadadustat [inn]

22. Vadadustat [jan]

23. Us8722895, 10: {[5-(3-chlorophenyl)-3-hydroxypyridine-2- Carbonyl]amino}-acetic Acid Trifluoroacetic Acid Salt

24. Vadadustat [who-dd]

25. Vadadustat (jan/usan/inn)

26. Schembl1920738

27. Chembl3646221

28. Gtpl11831

29. Bdbm107704

30. Dtxsid501179936

31. Amy27885

32. Bcp19497

33. Ex-a2573

34. 2-{[5-(3-chlorophenyl)-3-hydroxypyridin-2-yl]formamido}acetic Acid

35. Gsk128863

36. S6490

37. Zinc117532869

38. Cs-6373

39. Db12255

40. Sb19204

41. Us8598210, Table Xv, 10

42. Us8598210, Table Xv, 11

43. Ac-30928

44. As-71695

45. Db-102455

46. Hy-101277

47. Vadadustat; Pg-1016548; Akb-6548

48. J3.560.572j

49. C71001

50. D11078

51. Us8598210, 119

52. Q27280485

53. 2-(5-(3-chlorophenyl)-3-hydroxypicolinamido)acetic Acid

54. Akb-6548; B-506; Pg-1016548

55. {[5-(3-chlorophenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-acetic Acid

56. {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}-acetic Acid

2.4 Create Date

2008-01-07

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₁ClN₂O₄
Molecular Weight	306.70 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	306.0407345 g/mol
Monoisotopic Mass	306.0407345 g/mol
Topological Polar Surface Area	99.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	393
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