Lenvatinib Mesylate

Lenvatinib Mesylate (E7080 mesylate) is a first-line anticancer agent approved for the treatment of unresectable hepatocellular carcinoma, thyroid cancer, and metastatic renal cell carcinoma. As an oral multikinase inhibitor, Lenvatinib Mesylate targets VEGFR1–3, FGFR1–4, PDGFRα, and other receptor tyrosine kinases involved in tumor angiogenesis and proliferation. Lenvatinib Mesylate has also been designated as an orphan drug for the treatment of various types of thyroid cancer that do not respond to radioiodine. In pharmaceutical quality control, Lenvatinib Mesylate reference standards are used for analytical method development, method validation (AMV), and quality control (QC) applications. The bifurcated hydrogen bonds between adjacent urea groups in the Lenvatinib Mesylate molecular structure contribute to its unique physicochemical properties.

 

Product Parameters

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Parameter	Specification
Product Name	Lenvatinib Mesylate
CAS Number	857890-39-2
Molecular Formula	C₂₂H₂₃ClN₄O₇S
Molecular Weight	522.96 g/mol
Melting Point	>220 °C (dec.)
Appearance	White to off-white solid
Storage Condition	–20 °C Freezer

 

Application

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Lenvatinib mesylate is a multi-target tyrosine kinase inhibitor that may exert therapeutic effects against various cancers. Eisai is therefore conducting further studies on lenvatinib's efficacy in other malignancies, including hepatocellular carcinoma, non-small cell lung cancer, melanoma, breast cancer, lymphoma, and ovarian cancer. According to PharmaDex data retrieval, there are 62 clinical trial studies related to lenvatinib. In July 2017, Eisai submitted an application for the approval of lenvatinib as a first-line treatment for advanced hepatocellular carcinoma to both the U.S. FDA and the European Medicines Agency. Clinical trials have demonstrated that lenvatinib demonstrates superior efficacy compared to the current standard-of-care agent sorafenib in the treatment of intermediate-to advanced-stage hepatocellular carcinoma.

 

Bioactivity

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Lenvatinib mesylate (E7080) is a synthetic, orally active inhibitor of tyrosine kinases that targets vascular endothelial growth factor receptors (VEGFR1–3), fibroblast growth factor receptors (FGFR1–4), platelet-derived growth factor receptor (PDGFRα), stem cell factor receptor (Kit/c-Kit), and rearranged receptor tyrosine kinase (RET/c-RET). Lenvatinib mesylate exhibits potent antitumor activity.

 

Synthetic Route

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Synthesis of 4-[3-chloro-4-(cyclopropylamino-carbonyl)amino-phenoxy]-7-methoxy-6-quinolinformamide methanesulfonate. At 20°C to 35°C, dissolve 4-[3-chloro-4-(cyclopropylamino-carbonyl)amino-phenoxy]-7-methoxy-6-quinolinformamide (23.0 kg) in a mixture of methanesulfonic acid (5.44 kg) and acetic acid (150 L). Add methanesulfonic acid (777 g) to the solution, filter at 35°C or lower, and wash the filtrate with acetic acid (11.5 L). Adjust the filtrate temperature to 25°C–45°C, add 1-propanol (46.0 L) and seed crystals (230 g), then gradually add 1-propanol (161 L) and 23% isopropyl acetate (115 L). Cool the mixture to 15°C–25°C, filter to collect crystals, and wash them with a mixture of 1-propanol and isopropyl acetate (1-propanol concentration: 33 v/v%). Mix the wet crystals with ethanol (173 L) and stir for 3 hours at 20°C–60°C. Filter to obtain crystals, wash with ethanol, and dry under reduced pressure at 80°C or lower, yielding 4-[3-chloro-4-(cyclopropylamino-carbonyl)amino-phenoxy]-7-methoxy-6-quinolinformamide methanesulfonate (27.5 kg, yield: 94%).

 

Contact Us

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Looking for a reliable source of Lenvatinib Mesylate for your oncology API manufacturing or analytical development program? Contact Cosperpharm today for pricing, documentation, and technical support.