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    Bosutinib Monohydrate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Bosutinib hydrate, 918639-08-4, Ski-606 monohydrate, Bosutinib.h2o, Bosutinib (hydrate), 844zje6i55
    Molecular Formula
    C26H31Cl2N5O4
    Molecular Weight
    548.5  g/mol
    InChI Key
    BXPOSPOKHGNMEP-UHFFFAOYSA-N
    FDA UNII
    844ZJE6I55
    Bosutinib Monohydrate is the monohydrate form of bosutinib, 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.
    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;hydrate
    2.1.2 InChI
    InChI=1S/C26H29Cl2N5O3.H2O/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);1H2
    2.1.3 InChI Key
    BXPOSPOKHGNMEP-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.O
    2.2 Other Identifiers
    2.2.1 UNII
    844ZJE6I55
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Bosutinib Hydrate

    2. 918639-08-4

    3. Ski-606 Monohydrate

    4. Bosutinib.h2o

    5. Bosutinib (hydrate)

    6. 844zje6i55

    7. Bosutinib Hydrate (jan)

    8. 3-quinolinecarbonitrile, 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-, Hydrate (1:1)

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

    10. Bosutinib Hydrate [jan]

    11. Bosutinib (as Monohydrate)

    12. 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile Monohydrate

    13. 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile--water (1/1)

    14. Bosutinibhydrate

    15. Unii-844zje6i55

    16. Bosulif (tn)

    17. Schembl2887945

    18. Chebi:68533

    19. Dtxsid20238722

    20. Amy16532

    21. Bcp17036

    22. Hy-10158a

    23. Akos027326604

    24. Ac-30573

    25. Bosutinib Monohydrate [orange Book]

    26. Cs-0019907

    27. Bosutinib (as Monohydrate) [ema Epar]

    28. D09728

    29. A900109

    30. Q27137001

    31. 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl) Propoxy]-3-quinolinecarbonitrile Monohydrate

    32. 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile Monohydrate

    2.4 Create Date
    2007-02-05
    3 Chemical and Physical Properties
    Molecular Weight 548.5 g/mol
    Molecular Formula C26H31Cl2N5O4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass547.1753099 g/mol
    Monoisotopic Mass547.1753099 g/mol
    Topological Polar Surface Area83.9 Ų
    Heavy Atom Count37
    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 Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameBosulif
    PubMed HealthBosutinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Active IngredientBosutinib monohydrate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 500mg base
    Market StatusPrescription
    CompanyWyeth Pharms

    2 of 2  
    Drug NameBosulif
    PubMed HealthBosutinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Active IngredientBosutinib monohydrate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 500mg base
    Market StatusPrescription
    CompanyWyeth Pharms

    4.2 Drug Indication

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