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Chemistry

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Also known as: 380843-75-4, Ski-606, Bosutinib (ski-606), Ski 606, Bosulif, Ski606

Molecular Formula

C₂₆H₂₉Cl₂N₅O₃

Molecular Weight

530.4 g/mol

InChI Key

UBPYILGKFZZVDX-UHFFFAOYSA-N

FDA UNII

5018V4AEZ0

Bosutinib is a synthetic quinolone derivative and dual kinase inhibitor that targets both Abl and Src kinases with potential antineoplastic activity. Unlike imatinib, bosutinib inhibits the autophosphorylation of both Abl and Src kinases, resulting in inhibition of cell growth and apoptosis. Because of the dual mechanism of action, this agent may have activity in resistant CML disease, other myeloid malignancies and solid tumors. Abl kinase is upregulated in the presence of the abnormal Bcr-abl fusion protein which is commonly associated with chronic myeloid leukemia (CML). Overexpression of specific Src kinases is also associated with the imatinib-resistant CML phenotype.

Bosutinib is a Kinase Inhibitor. The mechanism of action of bosutinib is as a Bcr-Abl Tyrosine Kinase Inhibitor.

1 2D Structure

Bosutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile

2.1.2 InChI

InChI=1S/C26H29Cl2N5O3/c1-32-6-8-33(9-7-32)5-4-10-36-25-13-21-18(11-24(25)35-3)26(17(15-29)16-30-21)31-22-14-23(34-2)20(28)12-19(22)27/h11-14,16H,4-10H2,1-3H3,(H,30,31)

2.1.3 InChI Key

UBPYILGKFZZVDX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)CCCOC2=C(C=C3C(=C2)N=CC(=C3NC4=CC(=C(C=C4Cl)Cl)OC)C#N)OC

2.2 Other Identifiers

2.2.1 UNII

5018V4AEZ0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ski-606

2. Ski606

2.3.2 Depositor-Supplied Synonyms

1. 380843-75-4

2. Ski-606

3. Bosutinib (ski-606)

4. Ski 606

5. Bosulif

6. Ski606

7. 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile

8. 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

9. 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile

10. Bosutinib (usan)

11. Bosutinib [usan]

12. Sk-606

13. 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-3-quinolinecarbonitrile

14. Bosutinib Isomer 1

15. Chembl288441

16. 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile

17. 4-(2,4-dichloro-5-methoxyphenylamino)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile

18. Chebi:39112

19. 5018v4aez0

20. Ski-606)

21. Bosutinib (as Monohydrate)

22. Bosutinib [usan:inn]

23. Ncgc00241107-01

24. Unii-5018v4aez0

25. Mfcd07367846

26. Bosutinib,ski-606

27. Bosutinib [inn]

28. Bosutinib (ski606)

29. Bosutinib [mi]

30. Bosutinib [vandf]

31. Pf-5208763

32. Bosutinib - Ski-606

33. Bosutinib [mart.]

34. Ec 700-455-1

35. Bosutinib [who-dd]

36. Mls006011212

37. Schembl158390

38. Amy266

39. Bdbm4552

40. Gtpl5710

41. Bosutinib, >=98% (hplc)

42. Dtxsid10861568

43. Ex-a391

44. Bcpp000318

45. Hms2043a22

46. Hms3244a03

47. Hms3244a04

48. Hms3244b03

49. Hms3651c03

50. Hms3672k11

51. Hms3743e09

52. 2-pyridin-2-ylethylacetate

53. K00615a

54. Bcp01782

55. Nsc765694

56. Nsc799367

57. Sk 606

58. Zinc22448983

59. Akos015902521

60. Ac-2413

61. Bcp9000446

62. Ccg-208129

63. Cs-0118

64. Db06616

65. Nsc-765694

66. Nsc-799367

67. Pb30881

68. Ncgc00241107-03

69. Ncgc00241107-05

70. 4-(2,4-dichloro-5-methoxy-anilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile

71. As-11064

72. Hy-10158

73. Smr002530350

74. Ft-0656231

75. S1014

76. Ski606; Ski 606; Sk-i606

77. Sw220197-1

78. A25014

79. D03252

80. Ab01565836_03

81. 843b754

82. Q894611

83. Sr-01000941572

84. J-519931

85. Q-200745

86. Sr-01000941572-1

87. Brd-k99964838-001-01-0

88. Brd-k99964838-001-06-9

89. 3-quinolinecarbonitrile, 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-

90. 3-quinolinecarbonitrile, 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methyl-1-piperazinyl)propoxy)-

91. 4-(2,4-dichloro-5-methoxy-phenylamino)-6-methoxy-7-[3-(4-methyl-piperazin-1-yl)propoxy]quinoline-3-carbonitrile

92. Ski-606;4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile

2.4 Create Date

2006-01-30

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₉Cl₂N₅O₃
Molecular Weight	530.4 g/mol
XLogP3	5.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	529.1647452 g/mol
Monoisotopic Mass	529.1647452 g/mol
Topological Polar Surface Area	82.9 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	734
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 1
Drug Name	<a class="pubchem-internal-link multiple-CIDs" href="/compound/Bosulif">Bo
PubMed Health	<a class="pubchem-internal-link CID-5328940" href="/compound/Bosutinib"
Drug Classes	Antineoplastic Agent
Active Ingredient	Bosutinib monohydrate
Dosage Form	Tablet
Route	Oral
Strength	eq 100mg base; eq 500mg base
Market Status	Prescription
Company	Wyeth Pharms

4.2 Drug Indication

Treatment of chronic, accelerated, or blast phase Philadelphia chromosome-positive (Ph+) chronic myelogenous leukemia (CML) with resistance or intolerance to prior therapy in adult patients.

FDA Label

Bosulif is indicated for the treatment of adult patients with:

- newlydiagnosed chronic phase (CP) Philadelphia chromosome-positive chronic myelogenous leukaemia (Ph+ CML).

- CP, accelerated phase (AP), and blast phase (BP) Ph+ CML previously treated with one or more tyrosine kinase inhibitor(s) [TKI(s)] and for whom imatinib, nilotinib and dasatinib are not considered appropriate treatment options.

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Active Moiety

BOSUTINIB

5.1.2 FDA UNII

5018V4AEZ0

5.1.3 Pharmacological Classes

Kinase Inhibitor [EPC]; Bcr-Abl Tyrosine Kinase Inhibitors [MoA]

5.2 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EA - Bcr-abl tyrosine kinase inhibitors

L01EA04 - Bosutinib

5.3 Absorption, Distribution and Excretion

Absorption

Food increase the exposure of bosutinib. Tmax, single dose, cancer patients, fed-state = 4-6 hours; After 15 daily doses of bosutinib 500 mg with food in CML patients, the pharmacokinetic parameters are as follows: Cmax = 200 ng/mL; AUC = 3650 ngh/mL

Route of Elimination

When given a single oral dose, 91.3% of the dose was recovered in feces and 3% of the dose recovered in urine.

Volume of Distribution

Apparent volume of distribution = 6080 1230 L.

Clearance

Mean clearance (CL/F), single oral dose, fed-state = 189 L/h

5.4 Metabolism/Metabolites

Bosutinib is primarily metabolized by CYP3A4. The major circulating metabolites identified in plasma are oxydechlorinated (M2) bosutinib (19% of parent exposure) and N-desmethylated (M5) bosutinib (25% of parent exposure), with bosutinib N-oxide (M6) as a minor circulating metabolite. All the metabolites were deemed inactive.

5.5 Biological Half-Life

Terminal phase elimination half-life, single oral dose, fed-state = 22.5 hours

5.6 Mechanism of Action

Bosutinib is a tyrosine kinase inhibitor. Although it is able to inhibit several tyrosine kinases such as Src, Lyn, and Hck, which are members of the Src-family of kinases, its primary target is the Bcr-Abl kinase. The Bcr-Abl gene is a chimeric oncogene created from the fusion of the breakpoint-cluster (Bcr) gene and Abelson (Abl) tyrosine gene. This chromosomal abnormality results in the formation of what is commonly known as the Philadelphia chromosome or Philadelphia translocation. The Bcr-Abl gene expresses a particular kinase that promotes the progression of CML. A decrease in the growth and size of the CML tumour has been observed following administration of bosutinib. Bosutinib did not inhibit the T315I and V299L mutant cells.

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