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    Vadadustat

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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 Weight 306.70 g/mol
    Molecular Formula C14H11ClN2O4
    XLogP32.5
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass306.0407345 g/mol
    Monoisotopic Mass306.0407345 g/mol
    Topological Polar Surface Area99.5 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity393
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of anaemia due to chronic disorders

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    B - Blood and blood forming organs

    B03 - Antianemic preparations

    B03X - Other antianemic preparations

    B03XA - Other antianemic preparations

    B03XA08 - Vadadustat