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Quizartinib

Quizartinib

Synopsis, Chemistry

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Also known as: 950769-58-1, Ac220, Quizartinib (ac220), Ac-220, Ac 220, Quizartinib hcl

Molecular Formula

C₂₉H₃₂N₆O₄S

Molecular Weight

560.7 g/mol

InChI Key

CVWXJKQAOSCOAB-UHFFFAOYSA-N

FDA UNII

7LA4O6Q0D3

Quizartinib is an orally available small molecule with potential antineoplastic activity. Quizartinib selectively inhibits class III receptor tyrosine kinases, including FMS-related tyrosine kinase 3 (FLT3/STK1), colony-stimulating factor 1 receptor (CSF1R/FMS), stem cell factor receptor (SCFR/KIT), and platelet derived growth factor receptors (PDGFRs), resulting in inhibition of ligand-independent leukemic cell proliferation and apoptosis. Mutations in FLT3, resulting in constitutive activation, are the most frequent genetic alterations in acute myeloid leukemia (AML) and occur in approximately one-third of AML cases.

1 2D Structure

Quizartinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl]urea

2.1.2 InChI

InChI=1S/C29H32N6O4S/c1-29(2,3)25-17-26(33-39-25)32-27(36)30-20-6-4-19(5-7-20)22-18-35-23-9-8-21(16-24(23)40-28(35)31-22)38-15-12-34-10-13-37-14-11-34/h4-9,16-18H,10-15H2,1-3H3,(H2,30,32,33,36)

2.1.3 InChI Key

CVWXJKQAOSCOAB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)C1=CC(=NO1)NC(=O)NC2=CC=C(C=C2)C3=CN4C5=C(C=C(C=C5)OCCN6CCOCC6)SC4=N3

2.2 Other Identifiers

2.2.1 UNII

7LA4O6Q0D3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ac220 Compound

2.3.2 Depositor-Supplied Synonyms

1. 950769-58-1

2. Ac220

3. Quizartinib (ac220)

4. Ac-220

5. Ac 220

6. Quizartinib Hcl

7. Ac010220

8. Quizartinib Freebase

9. Ac 010220

10. Asp-2689

11. 1-(5-(tert-butyl)isoxazol-3-yl)-3-(4-(7-(2-morpholinoethoxy)benzo[d]imidazo[2,1-b]thiazol-2-yl)phenyl)urea

12. 7la4o6q0d3

13. Chembl576982

14. N-(5-tert-butylisoxazol-3-yl)-n'-{4-[7-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea

15. Chebi:90217

16. 950769-58-1 (free Base)

17. Ac-010220

18. 1132827-21-4 (hcl)

19. 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-{7-[2-(morpholin-4-yl)ethoxy]imidazo[2,1-b][1,3]benzothiazol-2-yl}phenyl)urea

20. 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-[6-(2-morpholin-4-ylethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl]urea

21. N-(5-tert-butyl-isoxazol-3-yl)-n'-{4-[7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea Dihydrochloride

22. Chembl2386811

23. 1-(5-(tert-butyl)isoxazol-3-yl)-3-(4-(7-(2-morpholinoethoxy)-benzo[d]imidazo[2,1-b]thiazol-2-yl)phenyl)urea

24. N-(5-(1,1-dimethylethyl)isoxazol-3-yl)-n'-(4-(7-(2-(morpholin-4-yl)ethoxy)imidazo(2,1- B)benzothiazol-2-yl)phenyl)urea

25. N-(5-(1,1-dimethylethyl)isoxazol-3-yl)-n'-(4-(7-(2-(morpholin-4-yl)ethoxy)imidazo(2,1-b)benzothiazol-2-yl)phenyl)urea

26. Urea, N-(5-(1,1-dimethylethyl)-3-isoxazolyl)-n'-(4-(7-(2-(4-morpholinyl)ethoxy) Imidazo(2,1-b)benzothiazol-2-yl)phenyl)-

27. Ac220 Compound

28. Ac220,quizartinib

29. Quizartinib [usan]

30. Quizartinib [usan:inn]

31. Quizartinibum

32. Unii-7la4o6q0d3

33. 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-(4-(7-(2-(morpholin-4-yl)ethoxy)imidazo(2,1-b)(1,3)benzothiazol-2-yl)phenyl)urea

34. N-(5-tert-butylisoxazol-3-yl)-n'-(4-(7-(2-(morpholin-4-yl)ethoxy)imidazo(2,1-b)(1,3)benzothiazol-2-yl)phenyl)urea

35. N-(5-tert-butylisoxazol-3-yl)-n'-[4-[7-[2-(morpholin-4-yl)ethoxy]imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl]urea

36. Quizartinib, 95%

37. Quizartinib, Ac220

38. Quizartinib, Free Base

39. Ac220 - Quizartinib

40. Quizartinib [mi]

41. Quizartinib; Plx3397

42. Quizartinib [inn]

43. Quizartinib (usan/inn)

44. Quizartinib, Ac010220

45. Schembl72923

46. Quizartinib [who-dd]

47. Mls006011240

48. Gtpl5658

49. Dtxsid70241746

50. Bcpp000443

51. Hms3244k09

52. Hms3244k10

53. Hms3244l09

54. Hms3265g09

55. Hms3265g10

56. Hms3265h09

57. Hms3265h10

58. Hms3654j20

59. Hms3743g21

60. Bcp02224

61. Bdbm50300690

62. Mfcd18074524

63. Nsc756647

64. Nsc799659

65. Nsc800857

66. S1526

67. Zinc43204002

68. Akos015891557

69. Bcp9000223

70. Ccg-264906

71. Cs-0211

72. Db12874

73. Nsc-756647

74. Nsc-799659

75. Nsc-800857

76. Sb16610

77. Ncgc00242493-01

78. Ncgc00242493-02

79. Ncgc00242493-07

80. As-16178

81. Hy-13001

82. Smr004703000

83. Ft-0687630

84. Sw218131-2

85. D09955

86. J-524214

87. Q7272714

88. Brd-k93918653-001-01-4

89. 3-(5-tert-butyl-1,2-oxazol-3-yl)-1-(4-{10-[2-(morpholin-4-yl)ethoxy]-7-thia-2,5-diazatricyclo[6.4.0.0^{2,6}]dodeca-1(12),3,5,8,10-pentaen-4-yl}phenyl)urea

90. N-(5-tert-butyl-isoxazol-3-yl)-n''-{4-[7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea

91. N-(5-tert-butyl-isoxazol-3-yl)-n'-(4-(7-(2-(morpholin-4-ylethoxy)imidazo(2,1-b) (1,3)benzothiazol-2-yl)phenyl)urea

92. N-(5-tert-butyl-isoxazol-3-yl)-n'-{4-[7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b][1,3]benzothiazol-2-yl]phenyl}urea

93. N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-n'-[4-[7-[2-(4-morpholinyl)ethoxy]imidazo[2,1-b]benzothiazol-2-yl]phenyl]urea

2.4 Create Date

2008-09-08

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₂N₆O₄S
Molecular Weight	560.7 g/mol
XLogP3	5.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	8
Exact Mass	560.22057470 g/mol
Monoisotopic Mass	560.22057470 g/mol
Topological Polar Surface Area	134 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	849
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 Indication

Treatment of acute myeloid leukaemia.

Treatment of acute myeloid leukaemia

5 Pharmacology and Biochemistry

5.1 Pharmacology

In preclinical studies, Quizartinib demonstrated dose-dependent activity and favorable drug-like profiles in bioavailability, pharmacokinetics, cytochrome P450 (CYP) liability, and absorption, distribution, metabolism, excretion (ADME).

5.2 ATC Code

L01XE

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EX - Other protein kinase inhibitors

L01EX11 - Quizartinib

5.3 Mechanism of Action

Quizartinib potently inhibits FLT3, a kinase that is mutated in approximately one-third of acute myeloid leukemia cases, and patients with FLT3 mutations are less responsive to traditional therapies.