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    Sorafenib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 475207-59-1, Nexavar, Sorafenib tosylate [usan], Sorafenib (tosylate), Sorafenib tosilate, Bay 54-9085
    Molecular Formula
    C28H24ClF3N4O6S
    Molecular Weight
    637.0  g/mol
    InChI Key
    IVDHYUQIDRJSTI-UHFFFAOYSA-N
    FDA UNII
    5T62Q3B36J
    A niacinamide and phenylurea derivative that inhibits multiple intracellular and cell surface kinases thought to be involved in ANGIOGENESIS, including RAF KINASES and VEGF RECEPTORS. It is used in the treatment of advanced RENAL CELL CARCINOMA and HEPATOCELLULAR CARCINOMA, and for treatment of THYROID CARCINOMA refractory to radioactive iodine therapy.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide;4-methylbenzenesulfonic acid
    2.1.2 InChI
    InChI=1S/C21H16ClF3N4O3.C7H8O3S/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25;1-6-2-4-7(5-3-6)11(8,9)10/h2-11H,1H3,(H,26,30)(H2,28,29,31);2-5H,1H3,(H,8,9,10)
    2.1.3 InChI Key
    IVDHYUQIDRJSTI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)S(=O)(=O)O.CNC(=O)C1=NC=CC(=C1)OC2=CC=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F
    2.2 Other Identifiers
    2.2.1 UNII
    5T62Q3B36J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(4-(3-(4-chloro-3-trifluoromethylphenyl)ureido)phenoxy)pyridine-2-carboxylic Acid Methyamide-4-methylbenzenesulfonate

    2. Bay 43 9006

    3. Bay 43-9006

    4. Bay 439006

    5. Bay 545 9085

    6. Bay 545-9085

    7. Bay 5459085

    8. Bay 673472

    9. Bay-545-9085

    10. Bay-673472

    11. Bay5459085

    12. Nexavar

    13. Sorafenib

    14. Sorafenib N Oxide

    15. Sorafenib N-oxide

    2.3.2 Depositor-Supplied Synonyms

    1. 475207-59-1

    2. Nexavar

    3. Sorafenib Tosylate [usan]

    4. Sorafenib (tosylate)

    5. Sorafenib Tosilate

    6. Bay 54-9085

    7. 475207-59-1 (tosylate)

    8. 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-n-methylpicolinamide 4-methylbenzenesulfonate

    9. Chebi:50928

    10. 5t62q3b36j

    11. Mfcd08235032

    12. Bay-54-9085

    13. Sorafenib Tosilate (jan)

    14. Sorafenib (nexavar)

    15. Sorafenib Tosylate (usan)

    16. Nexavar(r)

    17. Dsstox_cid_27817

    18. Dsstox_rid_82581

    19. Dsstox_gsid_47839

    20. 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-((2-(methylcarbamoyl)pyridin-4-yl)oxy)phenyl)urea Mono(4-methylbenzenesulfonate)

    21. 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-n2-methylpyridine-2-carboxamide Mono (4-methylbenzenesulfonate)

    22. 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide;4-methylbenzenesulfonic Acid

    23. Sorafenib Tosilate [jan]

    24. Bay 43-9006 Tosylate

    25. 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-n-methylpicolinamide 4-methylbenzenesulfonate.

    26. 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-n-methylpyridine-2-carboxamide; 4-methylbenzene-1-sulfonic Acid

    27. Cas-475207-59-1

    28. Nsc-724772

    29. Ncgc00167488-01

    30. Unii-5t62q3b36j

    31. Sr-00000000529

    32. Orafenib Tosylate

    33. Bay43-9006 Mono-p-tosylate

    34. Bay 43-9006 Mono-p-tosylate

    35. 4-(4-(((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl)amino)phenoxy)-n-methylpyridine-2-carboxamide 4-methylbenzenesulfonate

    36. 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-n-methylpyridine-2-carboxamide 4-methylbenzenesulfonate

    37. Nexavar (tn)

    38. Nsc724772

    39. Sorafenib - Nexavar

    40. Sorafenib Tsoh Salt

    41. Mls002415564

    42. Sorafenib Tosylate [mi]

    43. Chembl1200485

    44. Dtxsid9047839

    45. Sorafenib (bay-43-9006)

    46. Hms2219e08

    47. Hms3654i09

    48. Sorafenib, P-toluenesulfonate Salt

    49. Sorafenib Tosilate [mart.]

    50. Sorafenib Tosilate [who-dd]

    51. Sorafenib Tosylate [usp-rs]

    52. Tox21_112489

    53. Hy-10201a

    54. S1040

    55. Akos015924650

    56. Akos027469919

    57. Tox21_112489_1

    58. Ac-6799

    59. Ccg-208000

    60. Cs-0164

    61. Nd-0228

    62. Sorafenib Tosylate [orange Book]

    63. Ncgc00167488-08

    64. Sorafenib Tosilate [ep Monograph]

    65. 2-pyridinecarboxamide, 4-(4-((((4-chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-n-methyl-, Mono(4-methylbenzenesulfonate)

    66. Bs164414

    67. Smr001339079

    68. Sorafenib Tosylate [usp Monograph]

    69. Sy012324

    70. Bcp0726000112

    71. Am20090612

    72. Ft-0650737

    73. Ft-0698449

    74. Sw202562-3

    75. Ec-000.2356

    76. A25518

    77. D06272

    78. S-8502

    79. 207s591

    80. Q-201729

    81. Sr-00000000529-5

    82. 2,5-dioxo-1,4-cyclohexanedicarboxylicaciddimethylester

    83. Q27122250

    84. 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-n-methylpicolinamide Tosylate

    85. 2-pyridinecarboxamide, 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-n-methyl-, 4-methylbenzenesulfonate (1:1)

    86. 4-(4-(((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl)amino)phenoxy)-n-methylpyridine-2-carboxamide 4-methylbenzenesulphonate

    87. 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-n-methylpicolinamide4-methylbenzenesulfonate

    88. 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methyl-2-pyridinecarboxamide Tosylate

    89. 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-n-methylpyridine-2-carboxamide;hydron;4-methylbenzenesulfonate

    90. 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)-amino]phenoxy}-n-methylpyridine-2-carboxamide Tosylate

    91. 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-n -methylpyridine-2-carboxamide Tosylate

    92. 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-n-methylpyridine-2-carboxamide Tosylate

    93. 4-{4-[3-(4-chloro-3-trifluoromethyl-phenyl)-ureido]-phenoxy} -pyridine-2-carboxylic Acid Methylamide-4-methylbenzenesulfonate

    94. 4-{4-[3-(4-cl-3-trifluoromethyl-phenyl)-ureido]-phenoxy}-pyridine-2-carboxylic Acid Methylamide 4-methylbenzenesulfonate

    95. 4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)-n-(5-(4-methyl-1h-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide Monomethanesulfonate

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 637.0 g/mol
    Molecular Formula C28H24ClF3N4O6S
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count6
    Exact Mass636.1057179 g/mol
    Monoisotopic Mass636.1057179 g/mol
    Topological Polar Surface Area155 Ų
    Heavy Atom Count43
    Formal Charge0
    Complexity853
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameNexavar
    PubMed HealthSorafenib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelNEXAVAR, a kinase inhibitor, is the tosylate salt of sorafenib. Sorafenib tosylate has the chemical name 4-(4-{3-[4-Chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)N2-methylpyridine-2-carboxamide 4-methylbenzenesulfonate and its structural formula is...
    Active IngredientSorafenib tosylate
    Dosage FormTablet
    RouteOral
    Strengtheq 200mg base
    Market StatusPrescription
    CompanyBayer Hlthcare

    2 of 2  
    Drug NameNexavar
    PubMed HealthSorafenib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelNEXAVAR, a kinase inhibitor, is the tosylate salt of sorafenib. Sorafenib tosylate has the chemical name 4-(4-{3-[4-Chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)N2-methylpyridine-2-carboxamide 4-methylbenzenesulfonate and its structural formula is...
    Active IngredientSorafenib tosylate
    Dosage FormTablet
    RouteOral
    Strengtheq 200mg base
    Market StatusPrescription
    CompanyBayer Hlthcare

    4.2 Drug Indication

    * Hepatocellular carcinoma:

    Nexavar is indicated for the treatment of hepatocellular carcinoma.

    * Renal cell carcinoma:

    Nexavar is indicated for the treatment of patients with advanced renal cell carcinoma who have failed prior interferon-alpha or interleukin-2 based therapy or are considered unsuitable for such therapy.

    * Differentiated thyroid carcinoma:

    Nexavar is indicated for the treatment of patients with progressive, locally advanced or metastatic, differentiated (papillary/follicular/Hrthle cell) thyroid carcinoma, refractory to radioactive iodine.

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 ATC Code

    L01EX02