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Chemistry

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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

Sorafenib
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

Sorafenib

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


API Reference Price

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08-Mar-2021
31-Aug-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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Excipients by Applications

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Coating Systems & Additives

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Controlled & Modified Release

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Fillers, Diluents & Binders

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Direct Compression

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Thickeners and Stabilizers

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Disintegrants & Superdisintegrants

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Granulation

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Lubricants & Glidants

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Topical

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Co-Processed Excipients

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Film Formers & Plasticizers

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Taste Masking

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Solubilizers

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Empty Capsules

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Coloring Agents

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Vegetarian Capsules

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Rheology Modifiers

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Chewable & Orodispersible Aids

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API Stability Enhancers

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Emulsifying Agents

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Parenteral

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Surfactant & Foaming Agents

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DATA COMPILATION #PharmaFlow

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NEWS #PharmaBuzz

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Global Sales Information

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Market Place

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Patents & EXCLUSIVITIES

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REF. STANDARDS & IMPURITIES

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