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    Sunitinib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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