Lenvatinib

HCID 9823820

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

Lenvatinib417716-92-8E7080E-7080E 7080ER-203492-00Kisplyx4-{3-Chloro-4-[(Cyclopropylcarbamoyl)amino]phenoxy}-7-Methoxyquinoline-6-Carboxamide4-[3-chloro-4-(cyclopropylcarbamoylamino)phenoxy]-7-methoxyquinoline-6-carboxamideEE083865G2CHEBI:85994DTXSID50194605
Weitere Namen anzeigen
LenvimaLenvatinib (E7080)Lenvatinib-d4methyl 4-(4-amino-3-chlorophenoxy)-7-methoxyquinoline-6-carboxylate4-(3-chloro-4-(3-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamideCS-384E7081)Lenvatini
4-(3-chloro-4-(N'-cyclopropylureido)phenoxy)-7-methoxyquinoline-6-carboxamide4-(3-chloro-4-((cyclopropylaminocarbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide4-(3-CHLORO-4-((CYCLOPROPYLCARBAMOYL)AMINO)PHENOXY)-7-METHOXYQUINOLINE-6-CARBOXAMIDE6-QUINOLINECARBOXAMIDE, 4-(3-CHLORO-4-(((CYCLOPROPYLAMINO)CARBONYL)AMINO)PHENOXY)-7-METHOXY-lenvatinibum4-(3-chloro-4-(cyclopropylcarbamoylamino)phenoxy)-7-methoxyquinoline-6-carboxamide6-Quinolinecarboxamide, 4-[3-chloro-4-[[(cyclopropylamino)carbonyl]amino]phenoxy]-7-methoxy-RefChem:58936

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 3 Einträge

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

Dissociation Constants5.05

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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

Hazard Classes and CategoriesRepr. 2 (50%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

L01XE29

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingIn vitro binding of lenvatinib to human plasma proteins ranged from 98% to 99%.
Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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.

Biological Half-LifeThe terminal elimination half­life of lenvatinib is approximately 28 hours.
Metabolism/MetabolitesLenvatinib is metabolized by CYP3A and aldehyde oxidase.
Anwendungen · 2 Einträge

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.

Anbieter100 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
安礼特(上海)医药科技有限公司18109805911 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
上海波以尔化工有限公司[email protected]
Ergänzende Hinweise · 1 Eintrag

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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