Lenvatinib
Grundinformationen
- CAS
417716-92-8- Standard-SMILES
COc1cc2nccc(Oc3ccc(NC(=O)NC4CC4)c(Cl)c3)c2cc1C(N)=O- InChIKey
WOSKHXYHFSIKNG-UHFFFAOYSA-N- Summenformel
- C21H19ClN4O4
- Durchschnittliche Molmasse
- 426,9 g/mol
- Monoisotopische Masse
- 426,10948277
Überblick
Lenvatinib is a member of the class of quinolines that is the carboxamide of 4-{3-chloro-4-[(cyclopropylcarbamoyl)amino]phenoxy}-7-methoxyquinoline-6-carboxylic acid. A multi-kinase inhibitor and orphan drug used (as its mesylate salt) for the treatment of various types of thyroid cancer that do not respond to radioiodine. It has a role as an antineoplastic agent, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor, a fibroblast growth factor receptor antagonist, a vascular endothelial growth factor receptor antagonist and an orphan drug. It is a member of phenylureas, a member of quinolines, a monocarboxylic acid amide, an aromatic ether, a member of cyclopropanes, an aromatic amide and a member of monochlorobenzenes. It is a conjugate base of a lenvatinib(1+).
Namen und Bezeichner
- Bevorzugter Name
- Lenvatinib
- IUPAC
- 4-[3-chloro-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxyquinoline-6-carboxamide
- Englischer Name
- Lenvatinib
- Summenformel
- C21H19ClN4O4
- Molmasse
- 426.85
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
417716-92-8- PubChem CID
- 9823820
- DTXSID
DTXSID50194605- ChEMBL
CHEMBL1289601- ChEBI
CHEBI:85994- UNII
- EE083865G2
- EC Number
- 970-217-1
- Nikkaji
- J2.624.265G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,8
- Polarare Oberfläche (TPSA)
- 116 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 634
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors; Tyrosine Kinase Inhibitors
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
Physikochemische Eigenschaften
- Schmelzpunkt
- 216 °C · >216°C (dec.)
- Siedepunkt
- 627.2 · 627.2±55.0 °C(Predicted)
- Dichte
- 1.46 · 1.46
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Soluble in DMSO (up to 20 mg/ml)
- Aggregatzustand
- solid
- pka
- 13.09 · 13.09±0.70(Predicted)
- Farbe
- White
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- 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)
- InChIKey
- WOSKHXYHFSIKNG-UHFFFAOYSA-N
- SMILES
- N1C2C(=CC(C(N)=O)=C(OC)C=2)C(OC2=CC=C(NC(NC3CC3)=O)C(Cl)=C2)=CC=1
- CAS Datenbank
- 417716 · 417716-92-8
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Toxikologische Informationen
Hepatotoxicity
In large clinical trials of lenvatinib, elevations in serum aminotransferase levels were common, occurring in 52% of patients. Values greater than 5 times the upper limit of normal (ULN), however, occurred in only 3% to 5% of recipients. Serum alkaline phosphatase elevations were also common occurring in 28% of patients and were above 3 times ULN in 2%. In addition, fatal hepatic failure was reported in 3 of 1160 patients treated in preregistration clinical trials and another patient developed symptomatic but self-limited acute hepatitis with jaundice. The degree of relatedness of these events to lenvatinib therapy, however, was not defined. In the product label for lenvatinib, serum ALT, AST and alkaline phosphatase elevations are listed as adverse reactions, and acute hepatitis is mentioned as a rare occurrence. Monitoring of serum enzymes before, every 2 weeks for 2 months and monthly thereafter during treatment is recommended with dose reduction or discontinuation depending upon the degree and persistence of the abnormalities.
Adverse Effects
The most frequently observed adverse reactions of lenvatinib (≥30% of patients) include hypertension, fatigue, diarrhea, myalgia/arthralgia, reduced appetite, reduced body weight, stomatitis, headache, nausea, vomiting, abdominal pain, dysphonia, proteinuria, palmar-plantar erythrodysesthesia/hand-foot syndrome. Hypertension is one of the most common adverse effects of lenvatinib and is more prominent in subjects aged older than 75. During the phase III SELECT trials for radioactive iodine-refractory DIC, patients from the treatment group reported fistula formation causing bleeding from the tumor. Adverse effects from therapy should be managed supportively with dosing adjustments and discontinuation of treatment if necessary. Other reported adverse effects include the following. The description of severe adverse events includes:
Toxicity Summary
Fetal harm was observed in animal trials during the administration of lenvatinib at a dosage below the recommended range. No reproductive studies have been conducted to analyze the toxicity in humans. Pregnant women should be counseled and advised of possible toxicity to the fetus. Lenvatinib may be present during lactation, and halting breastfeeding is recommended for 1 week following the last dosage.
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L01XE29
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Pharmacodynamics
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.
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 (PDGFRα), KIT, and RET.
FDA Pharmacological Classification
EE083865G2
LENVATINIB
Established Pharmacologic Class [EPC] - Kinase Inhibitor
Mechanisms of Action [MoA] - Receptor Tyrosine Kinase Inhibitors
Lenvatinib is a Kinase Inhibitor. The mechanism of action of lenvatinib is as a Receptor Tyrosine Kinase Inhibitor.
LENVATINIB
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that inhibit PROTEIN KINASES.
Absorption, Distribution and Excretion
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.
Following administration of a radiolabeled dose, approximately 64% and 25% of the radiolabel were eliminated in the feces and urine, respectively.
Anwendungen
BeschreibungLenvatinib is an inhibitor of the receptor tyrosine kinases VEGF receptor 2 (VEGFR2) and VEGFR3 (IC50s = 4 and 5.2 nM, respectively). It also inhibits the related kinases VEGFR1, FGFR1, PDGFRα, PDGFRβ and Kit (IC50s = 22, 46, 51, 39, and 100 nM, respectively). Lenvatinib (30 mg/kg, twice per day) reduces tumor growth in an H146 small cell lung cancer mouse xenograft model and induces tumor regression when administered at a dose of 100 mg/kg twice per day. Formulations containing lenvatinib have been used in the treatment of differentiated thyroid cancer, renal cell carcinoma, and hepatocellular carcinoma.
VerwendenE7080 (Lenvatinib) is a multi-target inhibitor of VEGFR2 and VEGFR3 with IC50 of 4 nM and 5.2 nM, respectively.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter100 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A member of the class of quinolines that is the carboxamide of 4-{3-chloro-4-[(cyclopropylcarbamoyl)amino]phenoxy}-7-methoxyquinoline-6-carboxylic acid. A multi-kinase inhibitor and orphan drug used (as its mesylate salt) for the treatment of various types of thyroid cancer that do not respond to radioiodine.
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