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    Lenvatinib

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    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

    2D Structure

    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 Weight 426.9 g/mol
    Molecular Formula C21H19ClN4O4
    XLogP32.8
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count6
    Exact Mass426.1094828 g/mol
    Monoisotopic Mass426.1094828 g/mol
    Topological Polar Surface Area116 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity634
    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

    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

    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.