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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

Dasatinib
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 Weight 488.0 g/mol
Molecular Formula C22H26ClN7O2S
XLogP33.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Exact Mass487.1557220 g/mol
Monoisotopic Mass487.1557220 g/mol
Topological Polar Surface Area135 Ų
Heavy Atom Count33
Formal Charge0
Complexity642
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameSprycel
PubMed HealthDasatinib (By mouth)
Drug ClassesAntineoplastic Agent, Immunological Agent
Drug LabelSPRYCEL (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 IngredientDasatinib
Dosage FormTablet
Routeoral; Oral
Strength140mg; 100mg; 50mg; 80mg; 70mg; 20mg
Market StatusPrescription
CompanyBristol Myers Squibb

2 of 2  
Drug NameSprycel
PubMed HealthDasatinib (By mouth)
Drug ClassesAntineoplastic Agent, Immunological Agent
Drug LabelSPRYCEL (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 IngredientDasatinib
Dosage FormTablet
Routeoral; Oral
Strength140mg; 100mg; 50mg; 80mg; 70mg; 20mg
Market StatusPrescription
CompanyBristol 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


L01EA02


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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20-Jan-2021
17-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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01

2024 ACI Convention
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  • fda
  • EDQM
  • WHO-GMP

Virtual BoothShandong Boyuan is a Chinese manufacturer of GMP & CEP APIs & pharmaceutical intermediates.

CAS Number : 32955-21-8

End Use API : Dasatinib

About The Company : We are one of the well-known manufacturers of key APIs & intermediates in China, with 20 years of experience & presence in 20+ countries. At Boyuan, we are comm...

Shandong Boyuan Pharmaceutical

02

2024 ACI Convention
Not Confirmed
arrow
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothShandong Boyuan is a Chinese manufacturer of GMP & CEP APIs & pharmaceutical intermediates.

CAS Number : 302964-24-5

End Use API : Dasatinib

About The Company : We are one of the well-known manufacturers of key APIs & intermediates in China, with 20 years of experience & presence in 20+ countries. At Boyuan, we are comm...

Shandong Boyuan Pharmaceutical

03

2024 ACI Convention
Not Confirmed
arrow
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothShandong Boyuan is a Chinese manufacturer of GMP & CEP APIs & pharmaceutical intermediates.

CAS Number : 302964-08-5

End Use API : Dasatinib

About The Company : We are one of the well-known manufacturers of key APIs & intermediates in China, with 20 years of experience & presence in 20+ countries. At Boyuan, we are comm...

Shandong Boyuan Pharmaceutical

04

2024 ACI Convention
Not Confirmed
arrow
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothShandong Boyuan is a Chinese manufacturer of GMP & CEP APIs & pharmaceutical intermediates.

CAS Number : 302964-02-9

End Use API : Dasatinib

About The Company : We are one of the well-known manufacturers of key APIs & intermediates in China, with 20 years of experience & presence in 20+ countries. At Boyuan, we are comm...

Shandong Boyuan Pharmaceutical

05

2024 ACI Convention
Not Confirmed
arrow
2024 ACI Convention
Not Confirmed
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CAS Number : 863127-76-8

End Use API : Dasatinib

About The Company : Chengdu Yazhong Bio-pharmaceutical Co., Ltd., founded in 2002, is a leading company with plant extracts, APIs and medical intermediates. Our company is equipped...

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06

2024 ACI Convention
Not Confirmed
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2024 ACI Convention
Not Confirmed
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CAS Number : 302964-08-5

End Use API : Dasatinib

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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07

2024 ACI Convention
Not Confirmed
arrow
2024 ACI Convention
Not Confirmed
arrow

CAS Number : 302964-02-9

End Use API : Dasatinib

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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08

2024 ACI Convention
Not Confirmed
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2024 ACI Convention
Not Confirmed
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CAS Number : 302964-08-5

End Use API : Dasatinib

About The Company : Hunan Ouya Biological Company locates at Changsha National Biomedical Base; we are pharmaceutical manufacturer with integrated R&D, production and individual sa...

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09

2024 ACI Convention
Not Confirmed
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2024 ACI Convention
Not Confirmed
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CAS Number : 302964-24-5

End Use API : Dasatinib

About The Company : Hunan Ouya Biological Company locates at Changsha National Biomedical Base; we are pharmaceutical manufacturer with integrated R&D, production and individual sa...

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10

2024 ACI Convention
Not Confirmed
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2024 ACI Convention
Not Confirmed
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CAS Number : 353-83-3

End Use API : Dasatinib

About The Company : At Infinium Pharmachem Pvt. Ltd., we are well focused to Iodine chemistry & this is the only core area of ours. We are working as CRAMS, but our domain is very ...

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