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Ceritinib

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Chemistry

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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

Ceritinib

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 Formula	C₂₈H₃₆ClN₅O₃S
Molecular Weight	558.1 g/mol
XLogP3	6.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	557.2227389 g/mol
Monoisotopic Mass	557.2227389 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	835
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 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.

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