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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.


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LGM Pharma

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Shilpa Medicare

India

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Shilpa Medicare

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Synthon Pharmaceuticals

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Synthon Pharmaceuticals

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Wisdom Pharmaceutical

China

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Wisdom Pharmaceutical

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Zhejiang Jiuzhou Pharmaceutical

China

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Zhejiang Jiuzhou Pharmaceutical

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MSN Laboratories

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MSN Laboratories

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MSN Laboratories

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Alembic Pharmaceuticals Limited

India

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Alembic Pharmaceuticals Limited

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Hetero Drugs

India

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Hetero Drugs

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Sakar Healthcare

India

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Axitinib OH)

Date of Issue : 2022-06-17

Valid Till : 2025-07-02

Written Confirmation Number : WC-0082

Address of the Firm : API Division Kharakhadi, Plot No. 842-843, Kharakhadi, Padra Vadodara-391 450, G...

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Hetero Drugs

India
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Hetero Drugs

India
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Axitinib IH

Date of Issue : 2022-09-16

Valid Till : 2025-08-08

Written Confirmation Number : WC-0041

Address of the Firm : Unit-I, Survey No.10, I.D.A, Gaddapotharam Village, Jinnaram Mandal,Medak Dist, ...

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Hetero Drugs

India
26th North American ISSX
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Hetero Drugs

India
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Axitinib IH

Date of Issue : 2019-09-03

Valid Till : 2022-08-08

Written Confirmation Number : WC-0041A3

Address of the Firm : Unit-I, Survey No.10, I.D.A, Gaddapotharam Village, Jinnaram Mandal,Medak Dist, ...

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Axitinib IHS

Date of Issue : 2022-09-02

Valid Till : 2025-05-05

Written Confirmation Number : WC-0349

Address of the Firm : MIs. MSN Laboratories Private Limited, Unit-II, sv. No, 50, Kardanur (Village), ...

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Axitinib IH

Date of Issue : 2021-06-11

Valid Till : 2022-07-02

Written Confirmation Number : WC-0147A3

Address of the Firm : 100% EOU, Raichur Industrial Growth Centre, Plot No. 33, 33A, 40-47, Chicksugur-...

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API Reference Price

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17-Mar-2021
19-Apr-2024
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