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    Zykadia

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Ldk378, 1032900-25-6, Zykadia, Ldk-378, Nvp-ldk378-nx, Ldk 378
    Molecular Formula
    C28H36ClN5O3S
    Molecular Weight
    558.1  g/mol
    InChI Key
    VERWOWGGCGHDQE-UHFFFAOYSA-N
    FDA UNII
    K418KG2GET
    Ceritinib is an orally available inhibitor of the receptor tyrosine kinase activity of anaplastic lymphoma kinase (ALK) with antineoplastic activity. Upon administration, ceritinib binds to and inhibits wild-type ALK kinase, ALK fusion proteins and ALK point mutation variants. Inhibition of ALK leads to both the disruption of ALK-mediated signaling and the inhibition of cell growth in ALK-overexpressing tumor cells. ALK belongs to the insulin receptor superfamily and plays an important role in nervous system development. ALK dysregulation and gene rearrangements are associated with a variety of tumor cell types.
    Ceritinib is a Kinase Inhibitor. The mechanism of action of ceritinib is as a Tyrosine Kinase Inhibitor, and Cytochrome P450 3A Inhibitor, and Cytochrome P450 2C9 Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-chloro-2-N-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyphenyl)-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine
    2.1.2 InChI
    InChI=1S/C28H36ClN5O3S/c1-17(2)37-25-15-21(20-10-12-30-13-11-20)19(5)14-24(25)33-28-31-16-22(29)27(34-28)32-23-8-6-7-9-26(23)38(35,36)18(3)4/h6-9,14-18,20,30H,10-13H2,1-5H3,(H2,31,32,33,34)
    2.1.3 InChI Key
    VERWOWGGCGHDQE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=C(C=C1C2CCNCC2)OC(C)C)NC3=NC=C(C(=N3)NC4=CC=CC=C4S(=O)(=O)C(C)C)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    K418KG2GET
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-chloro-n2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-n4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

    2. Ldk378

    3. Zykadia

    2.3.2 Depositor-Supplied Synonyms

    1. Ldk378

    2. 1032900-25-6

    3. Zykadia

    4. Ldk-378

    5. Nvp-ldk378-nx

    6. Ldk 378

    7. 5-chloro-n2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-n4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine

    8. Ceritinib (ldk378)

    9. Ceritinib(ldk378)

    10. K418kg2get

    11. Nvp-ldk-378-nx

    12. Chembl2403108

    13. Chebi:78432

    14. 5-chloro-2-n-(5-methyl-4-piperidin-4-yl-2-propan-2-yloxyphenyl)-4-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine

    15. 2,4-pyrimidinediamine, 5-chloro-n4-(2-((1-methylethyl)sulfonyl)phenyl)-n2-(5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl)-

    16. 5-chloro-2-n-[5-methyl-4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl]-4-n-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine

    17. 5-chloro-n~2~-[5-methyl-4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl]-n~4~-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine

    18. 5-chloro-n2-(5-methyl-4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl)-n4-(2-(propane-2-sulfonyl)phenyl)pyrimidine-2,4-diamine

    19. 5-chloro-n2-[2-isopropoxy-5-methyl-4-(4-piperidyl)phenyl]-n4-(2-isopropylsulfonylphenyl)pyrimidine-2,4-diamine

    20. 5-chloro-n4-[2-[(1-methylethyl)sulfonyl]phenyl]-n2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-2,4-pyrimidinediamine

    21. 5-chloro-n4-[2-[(1methylethyl)sulfonyl]phenyl]-n2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-2,4-pyrimidinediamine;5-chloro-n4-[2-[(1methylethyl)sulfonyl]phenyl]-n2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-2,4-pyrimidinediamine

    22. Ceritinib [usan:inn]

    23. Unii-k418kg2get

    24. Ceritinibum

    25. Ceritinib[mi]

    26. 5-chloro-n2-[5-methyl-4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl]-n4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine

    27. Zykadia (tn)

    28. Ldk378 Certinib

    29. Ceritinib; Ldk378

    30. Ldk378(ceritinib)

    31. Ceritinib [inn]

    32. Ceritinib [jan]

    33. Eritinib (ldk378)

    34. Ceritinib [mi]

    35. Ceritinib [usan]

    36. Ceritinib [vandf]

    37. Ceritinib [who-dd]

    38. Ceritinib (jan/usan/inn)

    39. Gtpl7397

    40. Schembl1014329

    41. Ceritinib [orange Book]

    42. Dtxsid10725373

    43. Ex-a187

    44. Hms3652h22

    45. Hms3673i17

    46. Hms3747a11

    47. Amy10314

    48. Bcp07611

    49. Bdbm50436850

    50. Mfcd26142648

    51. Nsc776422

    52. Nsc777193

    53. Nsc800072

    54. Zinc96272772

    55. Akos025396438

    56. Ccg-264762

    57. Cs-1406

    58. Db09063

    59. Gs-6356

    60. Nsc-776422

    61. Nsc-777193

    62. Nsc-800072

    63. Sb16490

    64. Compound 15b [pmid 23742252]

    65. Ncgc00351603-10

    66. Ncgc00351603-13

    67. Ncgc00351603-15

    68. Ac-27469

    69. Hy-15656

    70. Ft-0697208

    71. S7083

    72. Sw219725-1

    73. D10551

    74. A852144

    75. J-690011

    76. Q21011233

    77. N-{2-methyl-5-[(methylamino)methyl]phenyl}-4-[(4-phenyl-2-quinazolinyl)amino]benzamide

    78. 4mk

    79. 5-chloro-n(2)-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-n(4)-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine

    80. 5-chloro-n2-(2-isopropoxy-5-methyl-4-piperidin-4-yl-phenyl)-n4-[2-(propane-2-sulfonyl)-phenyl]-pyrimidine-2,4-diamine

    81. 5-chloro-n2-(5-methyl-4-(piperidin-4-yl)-2-(propan-2-yloxy)phenyl)-n4-(2-(propane-2- Sulfonyl)phenyl)pyrimidine-2,4-diamine

    82. 5-chloro-n4-(2-((1-methylethyl)sulfonyl)phenyl)-n2-(5-methyl-2-(1-methylethoxy)-4- (piperidin-4-yl)phenyl)pyrimidine-2,4-diamine

    83. Ceritinib;5-chloro-n2-[2-isopropoxy-5-methyl-4-(4-piperidyl)phenyl]-n4-(2-isopropylsulfonylphenyl)pyrimidine-2,4-diamine;ceritinib

    84. N-{2-[(5-chloro-2-{[2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl]amino}pyrimidin-4-yl)amino]phenyl}propane-2-sulfonamide

    2.4 Create Date
    2012-07-16
    3 Chemical and Physical Properties
    Molecular Weight 558.1 g/mol
    Molecular Formula C28H36ClN5O3S
    XLogP36.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count9
    Exact Mass557.2227389 g/mol
    Monoisotopic Mass557.2227389 g/mol
    Topological Polar Surface Area114 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity835
    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 Indication

    Ceritinib is a kinase inhibitor indicated for the treatment of patients with anaplastic lymphoma kinase (ALK)-positive metastatic non-small cell lung cancer (NSCLC) who have progressed on or are intolerant to crizotinib. This indication is approved under accelerated approval based on tumor response rate and duration of response. An improvement in survival or disease-related symptoms has not been established. Continued approval for this indication may be contingent upon verification and description of clinical benefit in confirmatory trials.

    FDA Label

    Zykadia is indicated for the treatment of adult patients with anaplastic lymphoma kinase (ALK) positive advanced non small cell lung cancer (NSCLC) previously treated with crizotinib.

    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 FDA Pharmacological Classification
    5.2.1 Active Moiety
    CERITINIB
    5.2.2 FDA UNII
    K418KG2GET
    5.2.3 Pharmacological Classes
    Cytochrome P450 3A Inhibitors [MoA]; Kinase Inhibitor [EPC]; Tyrosine Kinase Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]
    5.3 ATC Code

    L01XE

    L01XE28

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01ED - Anaplastic lymphoma kinase (alk) inhibitors

    L01ED02 - Ceritinib

    5.4 Absorption, Distribution and Excretion

    Absorption

    After oral administration of ceritinib, peak concentrations were achieved after approximately 4 to 6 hours.

    Route of Elimination

    Following oral administration of a single 750 mg radiolabeled ceritinib dose, 92.3% of the administered dose was recovered in the feces (with 68% as unchanged parent compound) while 1.3% of the administered dose was recovered in the urine.

    Volume of Distribution

    The apparent volume of distribution (Vd/F) is 4230 L following a single 750 mg dose.

    Clearance

    The geometric mean apparent clearance (CL/F) of ceritinib was lower at steady-state (33.2 L/h) after 750 mg daily dosing than after a single 750 mg dose (88.5 L/h).

    5.5 Metabolism/Metabolites

    In vitro studies demonstrated that CYP3A was the major enzyme involved in the metabolic clearance of ceritinib. Following oral administration of a single 750 mg radiolabeled ceritinib dose, ceritinib as the parent compound was the main circulating component (82%) in human plasma.

    5.6 Biological Half-Life

    The terminal half life is 41 hours.

    5.7 Mechanism of Action

    Ceritinib inhibits Anaplastic lymphoma kinase (ALK) also known as ALK tyrosine kinase receptor or CD246 (cluster of differentiation 246), which is an enzyme that in humans is encoded by the ALK gene. About 4-5% of NSCLCs have a chromosomal rearrangement that generates a fusion gene between EML4 (echinoderm microtubule-associated protein-like 4) and ALK (anaplastic lymphoma kinase), which results in constitutive kinase activity that contributes to carcinogenesis and seems to drive the malignant phenotype. Ceritinib exerts its therapeutic effect by inhibiting autophosphorylation of ALK, ALK-mediated phosphorylation of the downstream signaling protein STAT3, and proliferation of ALK-dependent cancer cells. Ceritinib has been shown to inhibit in vitro proliferation of cell lines expressing EML4-ALK and NPM-ALK fusion proteins and demonstrated dose-dependent inhibition of EML4-ALK-positive NSCLC xenograft growth in mice and rats.