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Also known as: 417716-92-8, E7080, 4-(3-chloro-4-(3-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamide, E7080 (lenvatinib), Lenvatinib (e7080), E-7080

Molecular Formula

C₂₁H₁₉ClN₄O₄

Molecular Weight

426.9 g/mol

InChI Key

WOSKHXYHFSIKNG-UHFFFAOYSA-N

FDA UNII

EE083865G2

Lenvatinib is a synthetic, orally available inhibitor of vascular endothelial growth factor receptor 2 (VEGFR2, also known as KDR/FLK-1) tyrosine kinase with potential antineoplastic activity. Lenvatinib blocks VEGFR2 activation by VEGF, resulting in inhibition of the VEGF receptor signal transduction pathway, decreased vascular endothelial cell migration and proliferation, and vascular endothelial cell apoptosis.

Lenvatinib is a Kinase Inhibitor. The mechanism of action of lenvatinib is as a Receptor Tyrosine Kinase Inhibitor.

1 2D Structure

CAS 417716-92-8

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[3-chloro-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxyquinoline-6-carboxamide

2.1.2 InChI

InChI=1S/C21H19ClN4O4/c1-29-19-10-17-13(9-14(19)20(23)27)18(6-7-24-17)30-12-4-5-16(15(22)8-12)26-21(28)25-11-2-3-11/h4-11H,2-3H2,1H3,(H2,23,27)(H2,25,26,28)

2.1.3 InChI Key

WOSKHXYHFSIKNG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=CC2=NC=CC(=C2C=C1C(=O)N)OC3=CC(=C(C=C3)NC(=O)NC4CC4)Cl

2.2 Other Identifiers

2.2.1 UNII

EE083865G2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(3-chloro-4-(((cyclopropylamino)carbonyl)amino)phenoxy)-7-hydroxy-6-quinolinecarboxamide

2. 4-(3-chloro-4-((cyclopropylaminocarbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide

3. 4-(3-chloro-4-(n'-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamide

4. E 7080

5. E-7080

6. E-7080 Mesylate

7. E7080

8. E7080 Mesylate

9. Er-203492-00

10. Lenvatinib Mesilate

11. Lenvatinib Mesylate

12. Lenvatinib Metabolite M2

13. Lenvatinib Methanesulfonate

14. Lenvima

15. N-(4-((6-carbamoyl-7-methoxyquinolin-4-yl)oxy)-2-chlorophenyl)-n'-cyclopropylurea Monomethanesulfonate

2.3.2 Depositor-Supplied Synonyms

1. 417716-92-8

2. E7080

3. 4-(3-chloro-4-(3-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamide

4. E7080 (lenvatinib)

5. Lenvatinib (e7080)

6. E-7080

7. E 7080

8. Er-203492-00

9. Lenvatinib Free Base

10. Unii-ee083865g2

11. 4-{3-chloro-4-[(cyclopropylcarbamoyl)amino]phenoxy}-7-methoxyquinoline-6-carboxamide

12. 4-[3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy]-7-methoxy-6-quinolinecarboxamide

13. 4-[3-chloro-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxyquinoline-6-carboxamide

14. Chembl1289601

15. Chebi:85994

16. 417716-92-8 (free Base)

17. Ee083865g2

18. 4-(3-chloro-4-(n'-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamide

19. 4-(3-chloro-4-((cyclopropylaminocarbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide

20. 4-[3-chloro-4-[[(cyclopropylamino)carbonyl]amino]phenoxy]-7-methoxy-6-quinolinecarboxamide

21. Lenvatinib [usan]

22. Lenvatinib [usan:inn]

23. Kisplyx

24. 4-(3-chloro-4-((cyclopropylcarbamoyl)amino)phenoxy)-7-methoxyquinoline-6-carboxamide

25. 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide

26. Lev

27. Lenvatinib; E7080

28. Lenvatinib [mi]

29. Lenvatinib Base- Bio-x

30. Lenvatinib [inn]

31. Lenvatinib (usan/inn)

32. Lenvatinib [who-dd]

33. Mls006011239

34. Schembl864638

35. Gtpl7426

36. Amy9240

37. Dtxsid50194605

38. Ex-a249

39. Bcpp000247

40. Hms3244a07

41. Hms3244a08

42. Hms3244b07

43. Hms3654a14

44. Bcp01799

45. Zinc3816292

46. Bdbm50331094

47. Mfcd16038644

48. Nsc755980

49. Nsc800781

50. S1164

51. Akos025401742

52. Bcp9000633

53. Ccg-264842

54. Cs-0109

55. Db09078

56. Nsc-755980

57. Nsc-800781

58. Sb16580

59. Ncgc00263198-01

60. Ncgc00263198-04

61. Ncgc00263198-07

62. Ac-25047

63. As-16203

64. Bl164616

65. Hy-10981

66. Smr004702999

67. Db-070219

68. Ft-0700727

69. Sw219259-1

70. D09919

71. 716c928

72. A825653

73. J-513372

74. Q6523413

75. Brd-k39974922-001-02-7

76. 4-[3-chloranyl-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxy-quinoline-6-carboxamide

77. N-(4-((6-carbamoyl-7-methoxyquinolin-4-yl)oxy)-2-chlorophenyl)-n'-cyclopropylurea

78. 4-[3-chloro-4-[[(cyclopropylamino)-oxomethyl]amino]phenoxy]-7-methoxy-6-quinolinecarboxamide

79. 6-quinolinecarboxamide, 4-(3-chloro-4- (((cyclopropylamino)carbonyl)amino)phenoxy)-7-methoxy-

80. 6-quinolinecarboxamide, 4-(3-chloro-4-(((cyclopropylamino)carbonyl)amino)phenoxy)- 7-methoxy-

81. 6-quinolinecarboxamide, 4-(3-chloro-4-(((cyclopropylamino)carbonyl)amino)phenoxy)-7-methoxy-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₉ClN₄O₄
Molecular Weight	426.9 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	426.1094828 g/mol
Monoisotopic Mass	426.1094828 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	634
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

Lenvatinib is indicated for the treatment of following conditions. - Treatment of locally recurrent or metastatic, progressive, radioactive iodine-refractory differentiated thyroid cancer. - Treatment of advanced renal cell carcinoma (RCC) in combination with everolimus following one prior antiangiogenic therapy. - First-line treatment of unresectable hepatocellular carcinoma (HCC).

FDA Label

Lenvima is indicated as monotherapy for the treatment of adult patients with progressive, locally advanced or metastatic, differentiated (papillary/follicular/Hrthle cell) thyroid carcinoma (DTC), refractory to radioactive iodine (RAI).

Lenvima is indicated as monotherapy for the treatment of adult patients with advanced or unresectable hepatocellular carcinoma (HCC) who have received no prior systemic therapy.

Kisplyx is indicated for the treatment of adults with advanced renal cell carcinoma (RCC):

- in combination with pembrolizumab, as first-line treatment (see section 5. 1).

- in combination with everolimus, following one prior vascular endothelial growth factor (VEGF)-targeted therapy.

Treatment of follicular thyroid cancer , Treatment of osteosarcoma, Treatment of papillary thyroid cancer

Treatment of all conditions included in the category of malignant neoplasms except haematopoietic and lymphoid tissue neoplasms, papillary thyroid cancer , follicular thyroid cancer and osteosarcoma

5 Pharmacology and Biochemistry

5.1 Pharmacology

Based on x-ray crystallography and kinetic interaction studies, lenvatinib binds to the adenosine 5'-triphosphate binding site of VEGFR2 and to a neighbouring region via a cyclopropane ring and thereby inhibits tyrosine kinase activity and associated signalling pathways.

5.2 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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LENVATINIB

5.3.2 FDA UNII

EE083865G2

5.3.3 Pharmacological Classes

Receptor Tyrosine Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]

5.4 ATC Code

L01XE

L01XE29

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

L01EX - Other protein kinase inhibitors

L01EX08 - Lenvatinib

5.5 Absorption, Distribution and Excretion

Absorption

Time to peak plasma concentration occurred from 1 to 4 hours postdose. Administration with food did not affect the extent of absorption, but decreased the rate of absorption and delayed the median Tmax from 2 hours to 4 hours.

Route of Elimination

Following administration of a radiolabeled dose, approximately 64% and 25% of the radiolabel were eliminated in the feces and urine, respectively.

5.6 Metabolism/Metabolites

Lenvatinib is metabolized by CYP3A and aldehyde oxidase.

5.7 Biological Half-Life

The terminal elimination halflife of lenvatinib is approximately 28 hours.

5.8 Mechanism of Action

Lenvatinib is a receptor tyrosine kinase (RTK) inhibitor that inhibits the kinase activities of vascular endothelial growth factor (VEGF) receptors VEGFR1 (FLT1), VEGFR2 (KDR), and VEGFR3 (FLT4). Lenvatinib also inhibits other RTKs that have been implicated in pathogenic angiogenesis, tumor growth, and cancer progression in addition to their normal cellular functions, including fibroblast growth factor (FGF) receptors FGFR1, 2, 3, and 4; the platelet derived growth factor receptor alpha (PDGFR), KIT, and RET.

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