Lenvatinib mesylate

Base Information

• Chemical Name: Lenvatinib mesylate
• CAS No.: 857890-39-2
• Molecular Formula: C21H19ClN4O4.CH4O3S
• Molecular Weight: 522.966
• European Community (EC) Number: 812-398-0
• UNII: 3J78384F61
• DSSTox Substance ID: DTXSID90235081
• Wikidata: Q27158839
• NCI Thesaurus Code: C48636
• ChEMBL ID: CHEMBL2105704
• Mol file: 857890-39-2.mol

Synonyms:4-(3-chloro-4-(((cyclopropylamino)carbonyl)amino)phenoxy)-7-hydroxy-6-quinolinecarboxamide;4-(3-chloro-4-((cyclopropylaminocarbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide;4-(3-chloro-4-(N'-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamide;E 7080;E-7080;E-7080 mesylate;E7080;E7080 mesylate;ER-203492-00;lenvatinib;lenvatinib mesilate;lenvatinib mesylate;lenvatinib metabolite M2;lenvatinib methanesulfonate;Lenvima;N-(4-((6-carbamoyl-7-methoxyquinolin-4-yl)oxy)-2-chlorophenyl)-N'-cyclopropylurea monomethanesulfonate

Chemical Property of Lenvatinib mesylate

Chemical Property:

• PSA: 178.32000
• LogP: 5.82090
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 522.0975980
• Heavy Atom Count: 35
• Complexity: 727

Purity/Quality:

>95% ^*data from raw suppliers

LENVATINIBMESYLATE >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=NC=CC(=C2C=C1C(=O)N)OC3=CC(=C(C=C3)NC(=O)NC4CC4)Cl.CS(=O)(=O)O
• Recent ClinicalTrials: Lenvatinib for Advanced Bone and Soft Tissue Sarcoma
• Recent EU Clinical Trials: A Phase II study of pembrolizumab, lenvatinib and chemotherapy combination in first line extensive-stage small cell lung cancer (ES-SCLC)
• Recent NIPH Clinical Trials: All case study of Lenvima Capsule
• Description: Lenvatinib mesylate (lenvatinib) is an orally available, receptor‐type tyrosine kinase inhibitor, which was developed at Eisai in 2015. It was approved by the FDA in 2015 for the treatment of differentiated thyroid cancer that is either locally recurrent, metastatic, or progressive and did not respond to radioactive iodine treatment. In May 2016, the FDA approved the drug as a combination therapy with everolimus for the treatment of advanced renal cell carcinoma. Because VEGF (and fibroblast growth factor receptors, known as FGFRs) are thought to play a role in cardiovascular signaling pathways, VEGF2R and FGFR inhibition are thought to be the mechanisms behind the primary side effect of lenvatinib mesylate, which is hypertension.
• Uses: Lenvatinib Mesylate is used in preparation of anti-human CTLA4xPD-1 bispecific antibodies for diagnosis, prevention and treatment of tumor or anemia.

Technology Process of Lenvatinib mesylate

There total 16 articles about Lenvatinib mesylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

lenvatinib (417716-92-8) + methanesulfonic acid (75-75-2,98527-29-8) → 4-[3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy]-7-methoxy-6-quinoline-carboxamide methanesulfonate (857890-39-2)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 3.66667h;

Reference yield: 92.0%

methanesulfonic acid (75-75-2,98527-29-8) + 1-{2-chloro-4-[(6-cyano-7-methoxy-quinolin-4-yl)oxy]phenyl}-3-cyclopropylurea (1882873-21-3) → 4-[3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy]-7-methoxy-6-quinoline-carboxamide methanesulfonate (857890-39-2)

Guidance literature:

In ethanol; water; at 20 ℃; Solvent; Temperature; Industrial scale;

Reference yield:

{4-[(6-carbamoyl-7-methoxy-4-quinolyl)oxy]-2-chlorophenyl}amino-carboxylic acid phenyl ester (417722-95-3) + methanesulfonic acid (75-75-2,98527-29-8) + Cyclopropylamine (765-30-0) → 4-[3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy]-7-methoxy-6-quinoline-carboxamide methanesulfonate (857890-39-2)

Guidance literature:

{4-[(6-carbamoyl-7-methoxy-4-quinolyl)oxy]-2-chlorophenyl}amino-carboxylic acid phenyl ester; Cyclopropylamine; In N,N-dimethyl acetamide; at 25 - 30 ℃;

methanesulfonic acid; at 25 - 30 ℃;

upstream raw materials:

lenvatinib

methanesulfonic acid

4?(4?amino?3?chlorophenoxy)?7?methoxyquinoline?6?carboxamide

4-Amino-3-chlorophenol hydrochloride

Refernces

• 1、 -. "Synthesis method of lenvatinib and new intermediate". Paragraph 0049; 0062-0064. . Retrieved 2020/07/24.
• 2、 -. "Method for refining Lenvatinib mesylate". Paragraph 0033-0039. . Retrieved 2020/03/02.