Chemical Component Summary

Name4-{3-chloro-4-[(cyclopropylcarbamoyl)amino]phenoxy}-7-methoxyquinoline-6-carboxamide
Synonymslenvatinib
Identifiers4-[3-chloranyl-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxy-quinoline-6-carboxamide
FormulaC21 H19 Cl N4 O4
Molecular Weight426.853
TypeNON-POLYMER
Isomeric SMILESCOc1cc2c(cc1C(=O)N)c(ccn2)Oc3ccc(c(c3)Cl)NC(=O)NC4CC4
InChIInChI=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)
InChIKeyWOSKHXYHFSIKNG-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count49
Chiral Atom Count0
Bond Count52
Aromatic Bond Count17

Drug Info: DrugBank

DrugBank IDDB09078 
NameLenvatinib
Groups
  • approved
  • investigational
DescriptionLenvatinib 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 (PDGFRα), KIT, and RET. These receptor tyrosine kinases (RTKs) located in the cell membrane play a central role in the activation of signal transduction pathways involved in the normal regulation of cellular processes, such as cell proliferation, migration, apoptosis and differentiation, and in pathogenic angiogenesis, lymphogenesis, tumour growth and cancer progression. In particular, VEGF has been identified as a crucial regulator of both physiologic and pathologic angiogenesis and increased expression of VEGF is associated with a poor prognosis in many types of cancers. Lenvatinib is indicated for the treatment of patients with locally recurrent or metastatic, progressive, radioactive iodine (RAI)-refractory differentiated thyroid cancer. Most patients with thyroid cancer have a very good prognosis with treatment (98% 5 year survival rate) involving surgery and hormone therapy. However, for patients with RAI-refractory thyroid cancer, treatment options are limited and the prognosis is poor, leading to a push for the development of more targeted therapies such as lenvatinib.
Synonyms
  • Lenvatinib mesylate
  • Lenvatinib
  • 4-{3-chloro-4-[(cyclopropylcarbamoyl)amino]phenoxy}-7-methoxyquinoline-6-carboxamide
Brand Names
  • Kisplyx
  • Lenvima
IndicationLenvatinib is indicated for the treatment of the following cancerous conditions:[L41120] **Differentiated Thyroid Cancer (DTC)** - Treatment of locally recurrent or metastatic, progressive, radioactive iodine-refractory differentiated thyroid cancer **Renal Cell Carcinoma (RCC)** - First-line treatment, in combination with [pembrolizumab], in adult patients with advanced renal cell carcinoma (RCC) - Treatment of advanced renal cell carcinoma, in combination with [everolimus], in adult patients who have previously tried ≥1 anti-angiogenic therapy **Hepatocellular Carcinoma (HCC)** - First-line treatment of patients with unresectable hepatocellular carcinoma **Endometrial Carcinoma** - Treatment of advanced endometrial carcinoma that is not microsatellite instability-high (MSI-H) or mismatch repair deficient (dMMR), in combination with [pembrolizumab], in patients who have experienced disease progression following prior systemic therapy and are not candidates for curative surgery or radiation
Categories
  • Amides
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Substrates
  • Benzene Derivatives
ATC-CodeL01EX08
CAS number417716-92-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Vascular endothelial growth factor receptor 1MVSYWDTGVLLCALLSCLLLTGSSSGSKLKDPELSLKGTQHIMQAGQTLH...unknowninhibitor
Vascular endothelial growth factor receptor 2MQSKVLLAVALWLCVETRAASVGLPSVSLDLPRLSIQKDILTIKANTTLQ...unknowninhibitor
Vascular endothelial growth factor receptor 3MQRGAALCLRLWLCLGLLDGLVSGYSMTPPTLNITEESHVIDTGDSLSIS...unknowninhibitor
Fibroblast growth factor receptor 1MWSWKCLLFWAVLVTATLCTARPSPTLPEQAQPWGAPVEVESFLVHPGDL...unknowninhibitor
Fibroblast growth factor receptor 2MVSWGRFICLVVVTMATLSLARPSFSLVEDTTLEPEEPPTKYQISQPEVY...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1289601
PubChem 9823820
ChEMBL CHEMBL1289601
ChEBI CHEBI:85994
CCDC/CSD UWEXUS