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    Chemistry

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    Also known as: 388082-77-7, Tykerb, Tykerb ditosylate, Lapatinib (gw-572016) ditosylate, Tyverb, Lapatinib (ditosylate)
    Molecular Formula
    C43H42ClFN4O10S3
    Molecular Weight
    925.5  g/mol
    InChI Key
    UWYXLGUQQFPJRI-UHFFFAOYSA-N
    FDA UNII
    4WK72K94MC
    Lapatinib Ditosylate
    A quinazoline derivative that inhibits EPIDERMAL GROWTH FACTOR RECEPTOR and HER2 (RECEPTOR, ERBB-2) tyrosine kinases. It is used for the treatment of advanced or metastatic breast cancer, where tumors overexpress HER2.
    1 2D Structure

    Lapatinib Ditosylate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine;4-methylbenzenesulfonic acid
    2.1.2 InChI
    InChI=1S/C29H26ClFN4O4S.2C7H8O3S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19;2*1-6-2-4-7(5-3-6)11(8,9)10/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35);2*2-5H,1H3,(H,8,9,10)
    2.1.3 InChI Key
    UWYXLGUQQFPJRI-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)S(=O)(=O)O.CC1=CC=C(C=C1)S(=O)(=O)O.CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    4WK72K94MC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gw 282974x

    2. Gw 572016

    3. Gw-282974x

    4. Gw-572016

    5. Gw282974x

    6. Gw572016

    7. Lapatinib

    8. N-(3-chloro-4-(((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-methylsulfonyl)ethyl)amino)methyl) -2-furyl)-4-quinazolinamine

    9. Tykerb

    2.3.2 Depositor-Supplied Synonyms

    1. 388082-77-7

    2. Tykerb

    3. Tykerb Ditosylate

    4. Lapatinib (gw-572016) Ditosylate

    5. Tyverb

    6. Lapatinib (ditosylate)

    7. N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)quinazolin-4-amine Bis(4-methylbenzenesulfonate)

    8. 388082-78-8

    9. Lapatinib Ditosylate Anhydrous

    10. 4wk72k94mc

    11. 388082-77-7 (ditosylate)

    12. Bis(4-methylbenzene-1-sulfonic Acid); N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-amine

    13. Gw-572016

    14. 4-quinazolinamine, N-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-, Bis(4-methylbenzenesulfonate)

    15. N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)quinazolin-4-amine Ditosylate

    16. Sr-05000001472

    17. N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine;4-methylbenzenesulfonic Acid

    18. S1028

    19. Unii-4wk72k94mc

    20. Gw 572016f

    21. Gw-572016 Ditosylate

    22. Lapatinib Ditosylate,tykerb

    23. Schembl93590

    24. Quinazolin-4-amine Ditosylate

    25. Chembl1201183

    26. Dtxsid60959606

    27. Hms3265i13

    28. Hms3265i14

    29. Hms3265j13

    30. Hms3265j14

    31. Hms3654e07

    32. Hy-50898a

    33. Mfcd09264195

    34. Akos015888607

    35. Ac-5247

    36. Ccg-264661

    37. Cs-0831

    38. Gs-3661

    39. Db-119273

    40. Ft-0670728

    41. Lapatinib Ditoluenesulfonate Anhydrous

    42. Sw199101-4

    43. Ec-000.2339

    44. Lapatinib Ditosylate Anhydrous [who-dd]

    45. Gw 572016 Ditosylate;gw-572016 Ditosylate

    46. Lapatinib Ditoluenesulfonate Anhydrous [mi]

    47. Sr-05000001472-2

    48. Sr-05000001472-5

    49. Q27260601

    50. Z1692482592

    51. 4-methylbenzene-1-sulfonic Acid--n-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-[5-({[2-(methanesulfonyl)ethyl]amino}methyl)furan-2-yl]quinazolin-4-amine (2/1)

    52. 4-quinazolinamine, N-(3-chloro-4-((3-fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-, 4-methylbenzenesulfonate (1:2)

    53. N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)quinazolin-4-amine Bis(4-methylbenzenesulfona

    54. N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl) Ethylamino)methyl)furan-2-yl)quinazolin-4-amine Ditosylate

    55. N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylamino)methyl)furan-2-yl)quinazolin-4-amine Ditosylate

    56. N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-2-furyl]

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 925.5 g/mol
    Molecular Formula C43H42ClFN4O10S3
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count13
    Exact Mass924.1735629 g/mol
    Monoisotopic Mass924.1735629 g/mol
    Topological Polar Surface Area240 Ų
    Heavy Atom Count62
    Formal Charge0
    Complexity1100
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameTykerb
    PubMed HealthLapatinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelLapatinib is a small molecule and a member of the 4-anilinoquinazoline class of kinase inhibitors. It is present as the monohydrate of the ditosylate salt, with chemical name N-(3-chloro-4-{[(3-fluorophenyl)methyl]oxy}phenyl)-6-[5-({[2-(methylsulfony...
    Active IngredientLapatinib ditosylate
    Dosage FormTablet
    RouteOral
    Strengtheq 250mg base
    Market StatusPrescription
    CompanySmithkline Beecham

    2 of 2  
    Drug NameTykerb
    PubMed HealthLapatinib (By mouth)
    Drug ClassesAntineoplastic Agent
    Drug LabelLapatinib is a small molecule and a member of the 4-anilinoquinazoline class of kinase inhibitors. It is present as the monohydrate of the ditosylate salt, with chemical name N-(3-chloro-4-{[(3-fluorophenyl)methyl]oxy}phenyl)-6-[5-({[2-(methylsulfony...
    Active IngredientLapatinib ditosylate
    Dosage FormTablet
    RouteOral
    Strengtheq 250mg base
    Market StatusPrescription
    CompanySmithkline Beecham

    4.2 Drug Indication

    Tyverb is indicated for the treatment of patients with breast cancer , whose tumours overexpress HER2 (ErbB2):

    - in combination with capecitabine for patients with advanced or metastatic disease with progression following prior therapy, which must have included anthracyclines and taxanes and therapy with trastuzumab in the metastatic setting;

    - in combination with trastuzumab for patients with hormone-receptor-negative metastatic disease that has progressed on prior trastuzumab therapy or therapies in combination with chemotherapy;

    - in combination with an aromatase inhibitor for post-menopausal women with hormone-receptor-positive metastatic disease, not currently intended for chemotherapy. The patients in the registration study had not previously been treated with trastuzumab or an aromatase inhibitor. No data are available on the efficacy of this combination relative to trastuzumab in combination with an aromatase inhibitor in this patient population.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    5.2 ATC Code

    L01EH01

    API Reference Price

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    26-Apr-2021
    29-Aug-2024
    KGS
    overview
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