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Sunitinib Malate
Also known as: 341031-54-7, Sutent, Su011248 l-malate salt, Sunitinib malate [usan], Pha-290940ad, Su010398
Molecular Formula
C26H33FN4O7
Molecular Weight
532.6  g/mol
InChI Key
LBWFXVZLPYTWQI-IPOVEDGCSA-N
FDA UNII
LVX8N1UT73

An indole and pyrrole derivative that inhibits VEGFR-2 and PDGFR BETA RECEPTOR TYROSINE KINASES. It is used as an antineoplastic agent for the treatment of GASTROINTESTINAL STROMAL TUMORS, and for treatment of advanced or metastatic RENAL CELL CARCINOMA.
1 2D Structure

Sunitinib Malate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide;(2S)-2-hydroxybutanedioic acid
2.1.2 InChI
InChI=1S/C22H27FN4O2.C4H6O5/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28;5-2(4(8)9)1-3(6)7/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28);2,5H,1H2,(H,6,7)(H,8,9)/b17-12-;/t;2-/m.0/s1
2.1.3 InChI Key
LBWFXVZLPYTWQI-IPOVEDGCSA-N
2.1.4 Canonical SMILES
CCN(CC)CCNC(=O)C1=C(NC(=C1C)C=C2C3=C(C=CC(=C3)F)NC2=O)C.C(C(C(=O)O)O)C(=O)O
2.1.5 Isomeric SMILES
CCN(CC)CCNC(=O)C1=C(NC(=C1C)/C=C\2/C3=C(C=CC(=C3)F)NC2=O)C.C([C@@H](C(=O)O)O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
LVX8N1UT73
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-(5-fluoro-2-oxo-1,2-dihydroindolylidenemethyl)-2,4-dimethyl-1h-pyrrole-3-carboxylic Acid (2-diethylaminoethyl)amide

2. Su 011248

3. Su 11248

4. Su-011248

5. Su-11248

6. Su011248

7. Su11248

8. Sunitinib

9. Sutent

2.3.2 Depositor-Supplied Synonyms

1. 341031-54-7

2. Sutent

3. Su011248 L-malate Salt

4. Sunitinib Malate [usan]

5. Pha-290940ad

6. Su010398

7. Sunitinib L-malate

8. Su-011248 L-malate Salt

9. Lvx8n1ut73

10. Su-010398

11. (z)-n-(2-(diethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide (s)-2-hydroxysuccinate

12. Su 11248

13. N-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic Acid

14. Butanedioic Acid, Hydroxy-, (2s)-, Compd. With N-(2-(diethylamino)ethyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide (1:1)

15. N-(2-(diethylamino)ethyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide (2s)-hydroxybutanedioate

16. (2s)-2-hydroxybutanedioic Acid; N-[2-(diethylamino)ethyl]-5-{[(3z)-5-fluoro-2-oxo-2,3-dihydro-1h-indol-3-ylidene]methyl}-2,4-dimethyl-1h-pyrrole-3-carboxamide

17. Butanedioic Acid, 2-hydroxy-, (2s)-, Compd. With N-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide (1:1)

18. Su 011248

19. Unii-lvx8n1ut73

20. Butanedioic Acid, 2-hydroxy-, (2s)-, Compd. With N-(2-(diethylamino)ethyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide (1:1)

21. Mfcd08282795

22. Pdgf Tk Antagonist

23. Sutent (tn)

24. Sunitinib Malate- Bio-x

25. Sutent (tn) (pfizer)

26. Sunitinib Malate (sutent)

27. Chembl1567

28. Su 11248 (malate)

29. Su-11248 L-malate Salt

30. Sunitinib Malate [mi]

31. Sunitinib Malate (jan/usan)

32. Sunitinib Malate [jan]

33. Schembl1258610

34. Schembl1772213

35. Dtxsid4046492

36. Sunitinib Malate [vandf]

37. Sunitinib Malate [mart.]

38. Pnu-290940ad

39. Sunitinib Malate [who-dd]

40. Hms3261h09

41. Sunitinib Malate, >=98% (hplc)

42. Tox21_500514

43. Nsc736511

44. S1042

45. Su-11248j

46. Akos005145765

47. Akos025149097

48. Sunitinib Malate (sunitinib L-malate)

49. Sunitinib Malate [orange Book]

50. Ccg-221818

51. Cs-0177

52. Ks-5023

53. Ncgc00261199-01

54. Bs164428

55. Hy-10255

56. Am20090634

57. Sw219407-1

58. D06402

59. 031s547

60. A822079

61. J-019449

62. Q27283213

63. Sunitinib Malate

64. 341031-54-7

65. Sutent

66. Su-11248

67. Sunitinib

68. (2s)-2-hydroxybutanedioic Acid Compd. With N-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide (1:1)

69. (z)-n-(2-(diethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide(s)-2-hydroxysuccinate

70. 1h-pyrrole-3-carboxamide, N-(2-(diethylamino)ethyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-, (2s)-hydroxybutanedioate (1:1)

71. 1h-pyrrole-3-carboxamide,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl]-2,4-dimethyl-, (2s)-hydroxybutanedioate (1:1)

72. 1h-pyrrole-3-carboxamide,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl]-2,4-dimethyl-, Malate Salt

73. Butanedioic Acid, (2s)-, Compd. With N-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide (1:1)

74. Butanedioic Acid, (2s)-, Compd. With N-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide (1:1) (ca Index Name)

75. N-(2-diethylamino)ethyl)-5-((z)-(5-fluoro-2-oxo-1,2-dihydro-3h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide Hydrogen (2s)-2-hydroxybutanedioate

76. N-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidine)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide (2s)-2-hydroxybutanedioate Salt

2.4 Create Date
2006-04-29
3 Chemical and Physical Properties
Molecular Weight 532.6 g/mol
Molecular Formula C26H33FN4O7
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count10
Exact Mass532.23332757 g/mol
Monoisotopic Mass532.23332757 g/mol
Topological Polar Surface Area172 Ų
Heavy Atom Count38
Formal Charge0
Complexity765
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameSunitinib malate
Drug LabelSUTENT, an oral multi-kinase inhibitor, is the malate salt of sunitinib. Sunitinib malate is described chemically as Butanedioic acid, hydroxy-, (2S)-, compound with N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidine)meth...
Active IngredientSunitinib malate
Dosage FormCapsule
RouteOral
Strengtheq 50mg base; eq 12.5mg base; eq 25mg base; eq 37.5mg base
Market StatusPrescription
CompanyMylan Pharms

2 of 2  
Drug NameSunitinib malate
Drug LabelSUTENT, an oral multi-kinase inhibitor, is the malate salt of sunitinib. Sunitinib malate is described chemically as Butanedioic acid, hydroxy-, (2S)-, compound with N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidine)meth...
Active IngredientSunitinib malate
Dosage FormCapsule
RouteOral
Strengtheq 50mg base; eq 12.5mg base; eq 25mg base; eq 37.5mg base
Market StatusPrescription
CompanyMylan Pharms

4.2 Drug Indication

* Gastrointestinal stromal tumour (GIST):

Sutent is indicated for the treatment of unresectable and/or metastatic malignant gastrointestinal stromal tumour (GIST) in adults after failure of imatinib mesilate treatment due to resistance or intolerance.

* Metastatic renal cell carcinoma (MRCC):

Sutent is indicated for the treatment of advanced/metastatic renal cell carcinoma (MRCC) in adults.

* Pancreatic neuroendocrine tumours (pNET):

Sutent is indicated for the treatment of unresectable or metastatic, well-differentiated pancreatic neuroendocrine tumours with disease progression in adults.

Experience with Sutent as first-line treatment is limited (see section 5. 1).


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Protein Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
5.3 ATC Code

L01EX01


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