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    Chemistry

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    Also known as: 319460-85-0, Ag-013736, Inlyta, Ag 013736, (e)-n-methyl-2-((3-(2-(pyridin-2-yl)vinyl)-1h-indazol-6-yl)thio)benzamide, Ag-13736
    Molecular Formula
    C22H18N4OS
    Molecular Weight
    386.5  g/mol
    InChI Key
    RITAVMQDGBJQJZ-FMIVXFBMSA-N
    FDA UNII
    C9LVQ0YUXG
    Axitinib
    A benzamide and indazole derivative that acts as a TYROSINE KINASE inhibitor of the VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR. It is used in the treatment of advanced RENAL CELL CARCINOMA.
    Axitinib is a Kinase Inhibitor. The mechanism of action of axitinib is as a Receptor Tyrosine Kinase Inhibitor.
    1 2D Structure

    Axitinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-methyl-2-[[3-[(E)-2-pyridin-2-ylethenyl]-1H-indazol-6-yl]sulfanyl]benzamide
    2.1.2 InChI
    InChI=1S/C22H18N4OS/c1-23-22(27)18-7-2-3-8-21(18)28-16-10-11-17-19(25-26-20(17)14-16)12-9-15-6-4-5-13-24-15/h2-14H,1H3,(H,23,27)(H,25,26)/b12-9+
    2.1.3 InChI Key
    RITAVMQDGBJQJZ-FMIVXFBMSA-N
    2.1.4 Canonical SMILES
    CNC(=O)C1=CC=CC=C1SC2=CC3=C(C=C2)C(=NN3)C=CC4=CC=CC=N4
    2.1.5 Isomeric SMILES
    CNC(=O)C1=CC=CC=C1SC2=CC3=C(C=C2)C(=NN3)/C=C/C4=CC=CC=N4
    2.2 Other Identifiers
    2.2.1 UNII
    C9LVQ0YUXG
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ag 013736

    2. Ag-013736

    3. Ag013736

    4. Inlyta

    2.3.2 Depositor-Supplied Synonyms

    1. 319460-85-0

    2. Ag-013736

    3. Inlyta

    4. Ag 013736

    5. (e)-n-methyl-2-((3-(2-(pyridin-2-yl)vinyl)-1h-indazol-6-yl)thio)benzamide

    6. Ag-13736

    7. Ag013736

    8. C9lvq0yuxg

    9. N-methyl-2-((3-((1e)-2-(pyridin-2-yl)ethenyl)-1h-indazol-6-yl)sulfanyl)benzamide

    10. Nsc-757441

    11. Chebi:66910

    12. (e)-n-methyl-2-(3-(2-(pyridin-2-yl)vinyl)-1h-indazol-6-ylthio)benzamide

    13. N-methyl-2-[[3-[(e)-2-pyridin-2-ylethenyl]-1h-indazol-6-yl]sulfanyl]benzamide

    14. Nsc757441

    15. N-methyl-2-({3-[(e)-2-(pyridin-2-yl)ethenyl]-1h-indazol-6-yl}sulfanyl)benzamide

    16. Ncgc00241108-01

    17. S1005

    18. Dsstox_cid_28975

    19. Dsstox_rid_83240

    20. Dsstox_gsid_49049

    21. Axitinib (ag 013736)

    22. N-methyl-2-({3-[(e)-2-(pyridin-2-yl)vinyl]-1h-indazol-6-yl}sulfanyl)benzamide

    23. N-methyl-2-(3-((e)-2-pyridin-2-yl-vinyl)-1h-indazol-6-ylsulfanyl)-benzamide

    24. Axitinib [usan]

    25. Cas-319460-85-0

    26. Unii-c9lvq0yuxg

    27. Axitinibum

    28. Axitinib [usan:inn:jan]

    29. 4agc

    30. Benzamide, N-methyl-2-((3-((1e)-2-(2-pyridinyl)ethenyl)-1h-indazol-6-yl)thio)-

    31. Benzamide, N-methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1h-indazol-6-yl]thio]-

    32. Inlyta (tn)

    33. Mfcd09837898

    34. Ag13736

    35. 4ag8

    36. Axitinib (jan/usan)

    37. Axitinib [inn]

    38. Axitinib [jan]

    39. Axitinib [mi]

    40. Axitinib [vandf]

    41. Axitinib [mart.]

    42. Ag-013736;axitinib

    43. Axitinib [who-dd]

    44. Axitinib,ag-013736

    45. Mls006010164

    46. Schembl172918

    47. Axitinib [orange Book]

    48. Gtpl5659

    49. Axitinib, >=98% (hplc)

    50. Chembl1289926

    51. Dtxsid3049049

    52. N-methyl-2-[[3-[2-(2-pyridinyl)ethenyl]-1h-indazol-6-yl]thio]benzamide

    53. Schembl22930506

    54. Bdbm25117

    55. Chebi:94568

    56. Ex-a337

    57. Bcpp000372

    58. Bcp01371

    59. Zinc3816287

    60. Tox21_113597

    61. Nsc799341

    62. Akos015902898

    63. Tox21_113597_1

    64. Ac-1539

    65. Bcp9000345

    66. Ccg-264772

    67. Cs-0116

    68. Db06626

    69. Ks-1448

    70. Nsc 757441

    71. Nsc-799341

    72. Benzamide, N-methyl-2-((3-((e)-2-(2-pyridinyl)ethenyl)-1h-indazol-6-yl)thio)-

    73. Ncgc00241108-04

    74. Ncgc00241108-06

    75. Hy-10065

    76. Smr002530046

    77. Am20090673

    78. Sw219464-1

    79. D03218

    80. Ab01274739-01

    81. Ab01274739_02

    82. 460a850

    83. Sr-01000941566

    84. J-502064

    85. Q-200662

    86. Q4830631

    87. Sr-01000941566-1

    88. Brd-k29905972-001-01-4

    89. Brd-k29905972-001-02-2

    90. Benzamide, N-methyl-2-((3-((1e)-2-(2-pyridinyl)ethenyl)-1h-indazo)-6-yl)thio)-

    91. N-methyl-[[3[(1e)-2-(2-pyridinyl)ethenyl]-1h-indazol-6-yl]thio]-benzamide

    92. N-methyl-2((3-((1e0-2-(pyridin-2-yl)ethenyl)-1h-inazol-6-ylsufanyl)benzamide

    93. N-methyl-2-({3-[(e)-2-pyridin-2-ylethenyl]-2h-indazol-6-yl}sulfanyl)benzamide

    2.4 Create Date
    2006-04-29
    3 Chemical and Physical Properties
    Molecular Weight 386.5 g/mol
    Molecular Formula C22H18N4OS
    XLogP34.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass386.12013238 g/mol
    Monoisotopic Mass386.12013238 g/mol
    Topological Polar Surface Area96 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity557
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameInlyta
    PubMed HealthAxitinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelINLYTA (axitinib) is a kinase inhibitor. Axitinib has the chemical name N-methyl-2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylsulfanyl]-benzamide. The molecular formula is C22H18N4OS and the molecular weight is 386.47 Daltons. The chemical structur...
    Active IngredientAxitinib
    Dosage FormTablet
    RouteOral
    Strength1mg; 5mg
    Market StatusPrescription
    CompanyPfizer

    2 of 2  
    Drug NameInlyta
    PubMed HealthAxitinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelINLYTA (axitinib) is a kinase inhibitor. Axitinib has the chemical name N-methyl-2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylsulfanyl]-benzamide. The molecular formula is C22H18N4OS and the molecular weight is 386.47 Daltons. The chemical structur...
    Active IngredientAxitinib
    Dosage FormTablet
    RouteOral
    Strength1mg; 5mg
    Market StatusPrescription
    CompanyPfizer

    4.2 Drug Indication

    Used in kidney cell cancer and investigated for use/treatment in pancreatic and thyroid cancer.

    FDA Label

    Inlyta is indicated for the treatment of adult patients with advanced renal cell carcinoma (RCC) after failure of prior treatment with sunitinib or a cytokine.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Axitinib prevents the progression of cancer by inhibiting angiogenesis and blocking tumor growth.

    5.2 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.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    AXITINIB
    5.3.2 FDA UNII
    C9LVQ0YUXG
    5.3.3 Pharmacological Classes
    Receptor Tyrosine Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
    5.4 ATC Code

    L01EK01

    L01XE17

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EK - Vascular endothelial growth factor receptor (vegfr) tyrosine kinase inhibitors

    L01EK01 - Axitinib

    5.5 Absorption, Distribution and Excretion

    Absorption

    After one 5 mg dose of axitinib, it takes about 2.5 to 4.1 hours to reach maximum plasma concentration.

    Route of Elimination

    Axitinib is mainly eliminated unchanged in the feces (41%) with 12% of the original dose as unchanged axitinib. There is also 23% eliminated in the urine, most of which are metabolites.

    Volume of Distribution

    The volume of distribution is 160 L.

    Clearance

    The average clearance of axitinib is 38 L/h.

    5.6 Metabolism/Metabolites

    Axitinib undergoes mainly hepatic metabolism. CYP3A4 and CYP3A5 are the main hepatic enzymes while CYP1A2, CYP2C19, and UGT1A1 enzymes are secondary.

    5.7 Biological Half-Life

    Axitinib has a half life of 2.5 to 6.1 hours.

    5.8 Mechanism of Action

    Axitinib selectively blocks the tyrosine kinase receptors VEGFR-1 (vascular endothelial growth factor receptor), VEGFR-2, and VEGFR-3.

    API Reference Price

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    17-Mar-2021
    19-Apr-2024
    KGS
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    (KGS)    		 Average Price
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