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4 JDMF
9 EU WC
5 KDMF
20 NDC API
45 Listed Suppliers
$ API Reference Price

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360 FDF Dossiers, 36 FDA Orange Book, 49 Europe, 22 Canada, 196 Australia, 11 South Africa, 46 Listed Dossiers

360 FDF Dossiers
36 FDA Orange Book
49 Europe
22 Canada
196 Australia
11 South Africa
46 Listed Dossiers

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1 SPI Pharma, 2 Seqens, 2 DKSH, 3 Faran Shimi Pharmaceutical, 9 Gangwal Healthcare, 1 Nanjing Well Pharmaceutical, 1 ACG Worldwide, 3 Actylis, 5 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 8 BASF, 10 Corel Pharma Chem, 5 DFE Pharma, 1 Finar, 5 Gangwal Chemicals, 5 Ideal Cures Pvt Ltd, 1 Ingredion Pharma Solutions, 29 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 10 Microlex e.U, 2 Nomisma Healthcare, 1 Novo Excipients, 1 Pharmatrans-Sanaq, 3 Pluviaendo, 3 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 10 Roquette, 6 Seppic, 4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 10 Sigachi Industries, 2 The Dow Chemical Company, 3 Vasa Pharmachem

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3 DATA COMPILATION #PharmaFlow
44 NEWS #PharmaBuzz

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1 US Medicaid Prescriptions, 31 Finished Drug Prices, 15 Annual Reports

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1 US Medicaid Prescriptions
31 Finished Drug Prices
15 Annual Reports

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8 APIs, 7 FDF Dossiers

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8 APIs
7 FDF Dossiers

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66 US Patents, 36 US Exclusivities, 12 Health Canada Patents

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66 US Patents
36 US Exclusivities
12 Health Canada Patents

REF. STANDARDS & IMPURITIES

5 Others

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ANALYTICAL

1 BioAnalytical Methods

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1 BioAnalytical Methods

Naprod Dasatinib

Synopsis

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360

FDF Dossiers

FDA Orange Book

Europe

Canada

196

Australia

South Africa

Listed Dossiers

6DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

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News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

500,484,016

Annual Reports (USD Million)

19,219

Finished Drug Prices

157 RELATED EXCIPIENT COMPANIES

244EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 302962-49-8, Sprycel, Bms-354825, Dasatinib anhydrous, Bms 354825, Bms354825

Molecular Formula

C₂₂H₂₆ClN₇O₂S

Molecular Weight

488.0 g/mol

InChI Key

ZBNZXTGUTAYRHI-UHFFFAOYSA-N

FDA UNII

X78UG0A0RN

A pyrimidine and thiazole derived ANTINEOPLASTIC AGENT and PROTEIN KINASE INHIBITOR of BCR-ABL KINASE. It is used in the treatment of patients with CHRONIC MYELOID LEUKEMIA who are resistant or intolerant to IMATINIB.

Dasatinib anhydrous is a Kinase Inhibitor. The mechanism of action of dasatinib anhydrous is as a Protein Kinase Inhibitor, and Cytochrome P450 3A4 Inhibitor.

1 2D Structure

Dasatinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide

2.1.2 InChI

InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)

2.1.3 InChI Key

ZBNZXTGUTAYRHI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C(=CC=C1)Cl)NC(=O)C2=CN=C(S2)NC3=CC(=NC(=N3)C)N4CCN(CC4)CCO

2.2 Other Identifiers

2.2.1 UNII

X78UG0A0RN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (18f)-n-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide

2. 354825, Bms

3. Bms 354825

4. Bms-354825

5. Bms354825

6. N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide

7. Sprycel

2.3.2 Depositor-Supplied Synonyms

1. 302962-49-8

2. Sprycel

3. Bms-354825

4. Dasatinib Anhydrous

5. Bms 354825

6. Bms354825

7. Dasatinib (bms-354825)

8. Dasatinib (anhydrous)

9. N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide

10. N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide

11. N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide

12. N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide

13. Anh. Dasatinib

14. Anhydrous Dasatinib

15. Dasatinib (anh.)

16. Chembl1421

17. X78ug0a0rn

18. Chebi:49375

19. Dasatinib D8

20. Nsc732517

21. Nsc-732517

22. Nsc-759877

23. Ncgc00181129-01

24. Dsstox_cid_20979

25. Dsstox_rid_79608

26. Dsstox_gsid_40979

27. 5-thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)-1-piperazinyl)-2-methyl-4-pyrimidinyl)amino)-

28. Dasatinibum

29. Bms-354825 Hydrate

30. 5-thiazolecarboxamide, N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-

31. Smr002529551

32. Cas-302962-49-8

33. 302962-49-8 Pound Not863127-77-9

34. Dasatinib [usan:inn]

35. Unii-x78ug0a0rn

36. Bms Dasatinib

37. 1n1

38. Kinome_3650

39. Dasatinib (jan/inn)

40. Dasatinib [inn]

41. Dasatinib [mi]

42. N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide

43. Sprycel (bristol Meyers)

44. Dasatinib [who-dd]

45. Schembl8226

46. Dasatinib,bms-354825

47. Mls003915609

48. Mls004774145

49. Mls006010904

50. Dasatinib - Bms-354825

51. Gtpl5678

52. Dtxsid4040979

53. Bdbm13216

54. Cid_3062316

55. Ex-a401

56. 5-thiazolecarboxamide, Monohydrate

57. Bcpp000263

58. Hms2043n05

59. Hms3244a05

60. Hms3244a06

61. Hms3244b05

62. Hms3265c19

63. Hms3265c20

64. Hms3265d19

65. Hms3265d20

66. Hms3654k05

67. Hms3744c11

68. Pharmakon1600-01502275

69. Bcp01797

70. Zinc3986735

71. Tox21_112736

72. Mfcd11046566

73. Nsc759877

74. Nsc800087

75. S1021

76. Akos015902363

77. Tox21_112736_1

78. Bcp9000589

79. Bms 345825

80. Ccg-264779

81. Cs-0100

82. Db01254

83. Gs-6548

84. Nsc-800087

85. Sb17284

86. Ncgc00181129-02

87. Ncgc00181129-03

88. Ncgc00181129-05

89. Ncgc00181129-06

90. Ncgc00181129-07

91. Ncgc00181129-12

92. Ncgc00181129-14

93. Ncgc00181129-22

94. Ncgc00481571-01

95. 2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)-n-(2-chloro-6-methylphenyl)thiazole-5-carboxamide

96. Ac-22749

97. Bcb03_000715

98. Bms 35482513

99. Hy-10181

100. N-(2-chloro-6-methyl-phenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methyl-pyrimidin-4-yl]amino]thiazole-5-carboxamide

101. Am20080877

102. D5949

103. Ft-0650671

104. Sw208076-5

105. Ec-000.2122

106. D-3307

107. D03658

108. Ab01273956-01

109. Ab01273956-02

110. Ab01273956_03

111. Ar-270/43507994

112. Q419940

113. Sr-00000000554

114. Q-101345

115. Sr-00000000554-5

116. Brd-k49328571-001-05-1

117. Brd-k49328571-001-07-7

118. Bms-354825;bms354825;bms 354825

119. Z2786158251

120. N-(2-chloro-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl}amino)-1,3-thiazole-5-carboxamide

121. N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₆ClN₇O₂S
Molecular Weight	488.0 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	487.1557220 g/mol
Monoisotopic Mass	487.1557220 g/mol
Topological Polar Surface Area	135 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	642
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Sprycel
PubMed Health	Dasatinib (By mouth)
Drug Classes	Antineoplastic Agent, Immunological Agent
Drug Label	SPRYCEL (dasatinib) is a kinase inhibitor. The chemical name for dasatinib is N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide, monohydrate. The molecular formula is C22H26ClN7O2...
Active Ingredient	Dasatinib
Dosage Form	Tablet
Route	oral; Oral
Strength	140mg; 100mg; 50mg; 80mg; 70mg; 20mg
Market Status	Prescription
Company	Bristol Myers Squibb

2 of 2
Drug Name	Sprycel
PubMed Health	Dasatinib (By mouth)
Drug Classes	Antineoplastic Agent, Immunological Agent
Drug Label	SPRYCEL (dasatinib) is a kinase inhibitor. The chemical name for dasatinib is N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide, monohydrate. The molecular formula is C22H26ClN7O2...
Active Ingredient	Dasatinib
Dosage Form	Tablet
Route	oral; Oral
Strength	140mg; 100mg; 50mg; 80mg; 70mg; 20mg
Market Status	Prescription
Company	Bristol Myers Squibb

4.2 Drug Indication

For the treatment of adults with chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia with resistance or intolerance to prior therapy. Also indicated for the treatment of adults with Philadelphia chromosome-positive acute lymphoblastic leukemia with resistance or intolerance to prior therapy.

FDA Label

Sprycel is indicated for the treatment of paediatric patients with:

newly diagnosed Philadelphia chromosome-positive chronic myelogenous leukaemia in chronic phase (Ph+ CML CP) or Ph+ CML CP resistant or intolerant to prior therapy including imatinib. newly diagnosed Ph+ acute lymphoblastic leukaemia (ALL) in combination with chemotherapy.

Sprycel is indicated for the treatment of adult patients with:

- newly diagnosed Philadelphia-chromosome-positive (Ph+) chronic myelogenous leukaemia (CML) in the chronic phase;

- chronic, accelerated or blast phase CML with resistance or intolerance to prior therapy including imatinib mesilate;

- Ph+ acute lymphoblastic leukaemia (ALL) and lymphoid blast CML with resistance or intolerance to prior therapy.

Sprycel is indicated for the treatment of paediatric patients with:

- newly diagnosed Ph+ CML in chronic phase (Ph+ CML-CP) or Ph+ CML-CP resistant or intolerant to prior therapy including imatinib.

Treatment of Philadelphia-chromosome (BCR-ABL translocation)-positive acute lymphoblastic leukaemia, Treatment of Philadelphia-chromosome (BCR-ABL translocation)-positive chronic myeloid leukaemia

Dasatinib Accord is indicated for the treatment of adult patients with:

Ph+ acute lymphoblastic leukaemia (ALL) with resistance or intolerance to prior therapy.

Dasatinib Accord is indicated for the treatment of paediatric patients with:

newly diagnosed Ph+ ALL in combination with chemotherapy.

Dasatinib Accordpharma is indicated for the treatment of adult patients with:

newly diagnosed Philadelphia chromosome positive (Ph+) chronic myelogenous leukaemia (CML) in the chronic phase.

chronic, accelerated or blast phase CML with resistance or intolerance to prior therapy including imatinib.

Ph+ acute lymphoblastic leukaemia (ALL) and lymphoid blast CML with resistance or intolerance to prior therapy.

Dasatinib Accordpharma is indicated for the treatment of paediatric patients with:

newly diagnosed Ph+ CML in chronic phase (Ph+ CML-CP) or Ph+ CML-CP resistant or intolerant to prior therapy including imatinib.

newly diagnosed Ph+ ALL in combination with chemotherapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dasatinib is an oral dual BCR/ABL and Src family tyrosine kinase inhibitor

5.2 MeSH Pharmacological Classification

Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

DASATINIB ANHYDROUS

5.3.2 FDA UNII

X78UG0A0RN

5.3.3 Pharmacological Classes

Kinase Inhibitor [EPC]; Protein Kinase Inhibitors [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]

5.4 ATC Code

L01EA02

L01XE06

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

L01EA - Bcr-abl tyrosine kinase inhibitors

L01EA02 - Dasatinib

5.5 Absorption, Distribution and Excretion

Route of Elimination

Dasatinib is extensively metabolized in humans, primarily by the cytochrome P450 enzyme 3A4. Elimination is primarily via the feces.

Volume of Distribution

2505 L

5.6 Metabolism/Metabolites

Dasatinib is extensively metabolized in humans, primarily by the cytochrome P450 enzyme 3A4

5.7 Biological Half-Life

The overall mean terminal half-life of dasatinib is 3-5 hours.

5.8 Mechanism of Action

Dasatinib, at nanomolar concentrations, inhibits the following kinases: BCR-ABL, SRC family (SRC, LCK, YES, FYN), c-KIT, EPHA2, and PDGFRβ. Based on modeling studies, dasatinib is predicted to bind to multiple conformations of the ABL kinase. In vitro, dasatinib was active in leukemic cell lines representing variants of imatinib mesylate sensitive and resistant disease. Dasatinib inhibited the growth of chronic myeloid leukemia (CML) and acute lymphoblastic leukemia (ALL) cell lines overexpressing BCR-ABL. Under the conditions of the assays, dasatinib was able to overcome imatinib resistance resulting from BCR-ABL kinase domain mutations, activation of alternate signaling pathways involving the SRC family kinases (LYN, HCK), and multi-drug resistance gene overexpression.

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