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    Bosutinib

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

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    2D Structure
    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

    2D Structure

    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 Weight 530.4 g/mol
    Molecular Formula C26H29Cl2N5O3
    XLogP35.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count9
    Exact Mass529.1647452 g/mol
    Monoisotopic Mass529.1647452 g/mol
    Topological Polar Surface Area82.9 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity734
    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 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 ClassesAntineoplastic Agent
    Active IngredientBosutinib monohydrate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 500mg base
    Market StatusPrescription
    CompanyWyeth 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.