Capmatinib

HCID 25145656

Grundinformationen

CAS
1029712-80-8
Standard-SMILES
CNC(=O)c1ccc(-c2cnc3ncc(Cc4ccc5ncccc5c4)n3n2)cc1F
InChIKey
LIOLIMKSCNQPLV-UHFFFAOYSA-N
Summenformel
C23H17FN6O
Durchschnittliche Molmasse
412,4 g/mol
Monoisotopische Masse
412,14478738

Überblick

Capmatinib is a member of the class of imidazotriazines that is imidazo[1,2-b][1,2,4]triazine substituted by 3-fluoro-4-(methylcarbamoyl)phenyl and quinolin-6-ylmethyl groups at positions 2 and 7, respectively. It is a c-Met receptor tyrosine kinase inhibitor used for the treatment of non-small cell lung cancer with MET exon 14 skipping mutation. It has a role as an antineoplastic agent, a hepatotoxic agent, an apoptosis inducer and a c-Met tyrosine kinase inhibitor. It is a secondary carboxamide, a member of benzamides, a member of quinolines, an imidazotriazine and a member of monofluorobenzenes.

Namen und Bezeichner

Bevorzugter Name
Capmatinib
IUPAC
2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide
Englischer Name
Capmatinib
Summenformel
C23H17FN6O
Molmasse
412.42

Namen und Synonyme

capmatinib1029712-80-8INCB28060INC-2802-fluoro-N-methyl-4-(7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl)benzamideINCB-28060NVP-INC280-NXINCB 28060NVP-INC280TY34L4F9OZ2-fluoro-N-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamideINCB-28060 FREE BASE
Weitere Namen anzeigen
INC280INC280602-Fluoro-N-Methyl-4-(7-quinolin-6-ylMethyl-iMidazo[1,2-b][1,2,4] triazin-2-yl)-benzaMideNC280CS-192Karma for,
DTXSID901455952-fluoro-N-methyl-4-{7-[(quinolin-6-yl)methyl]imidazo[1,2-b][1,2,4]triazin-2-yl}benzamide2-fluoro-N-methyl-4-(7-(quinolin-6-ylmethyl)imidazo(1,2-b)(1,2,4)triazin-2-yl)benzamidecapmatinibum2-fluoro-N-methyl-4-(7-((quinolin-6-yl)methyl)imidazo(1,2-b)(1,2,4)triazin-2-yl)benzamideRefChem:57919DTXCID4068086INCB028060

Datenbank-Bezeichner

CAS
1029712-80-8
PubChem CID
25145656
DTXSID
DTXSID90145595
ChEMBL
CHEMBL3188267
ChEBI
CHEBI:231693
UNII
TY34L4F9OZ
EC Number
813-241-9
Nikkaji
J3.320.942H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,9
Polarare Oberfläche (TPSA)
85,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
4
Schwere Atome
31

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 2 Einträge

Breast Feeding; Lactation; Milk, Human; Enzyme Inhibitors; Protein Kinase Inhibitors; Signal Transduction Inhibitors

EMA approved medicines: Human medicine

Physikochemische Eigenschaften

Schmelzpunkt
250 °C · >250°C (dec.)
Dichte
1.4 · 1.40
Dampfdruck
0 · 0-0Pa at 20-25℃
storage temp.
-20 °C · -20°C Freezer, Under inert atmosphere
Löslichkeit
DMSO (Slightly), Methanol (Slightly)
pka
13.82 · 13.82±0.46(Predicted)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P264, P270, P273, P280, P301+P316, P318, P319, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 8 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 19-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34794
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

In the prelicensure clinical trials of capmatinib in patients with solid tumors harboring MET mutations, liver test abnormalities were frequent although usually self-limited and mild. Some degree of ALT elevations arose in 39% of capmatinib treated patients and were above 5 times the upper limit of normal (ULN) in 7%. In these trials that enrolled 373 patients, capmatinib was discontinued early due to increased AST or ALT in only 1% of patients. The liver test abnormalities had a median onset of 2 months after initiation of therapy. While serum aminotransferase elevations were occasionally quite high (5 to 20 times upper limit of normal), there were no accompanying elevations in serum bilirubin and no patient developed clinically apparent liver injury with jaundice. The product label for capmatinib recommends monitoring for routine liver tests before, at 2-week intervals during the first 3 months of therapy, and monthly thereafter as clinically indicated. However, since its approval and more wide-spread clinical use, there have been several reports of acute liver injury with jaundice in patients receiving capmatinib. The onset is after 6 to 8 weeks, and the clinical pattern is hepatocellular with features resembling severe acute viral hepatitis. Immune allergic and autoimmune features are not common, and recovery occurs typically within 2 to 3 months, but at least one fatal incident has been reported. Strikingly, most cases have occurred shortly after previous chemotherapy with a checkpoint inhibitor (within 2 to 4 months of the last dose). A similar frequent occurrence of liver injury following recent use of checkpoint inhibitors has been reported with other kinase inhibitors (sotorasib, crizotinib, osimertinib). These findings suggest that capmatinib not be started within 4 months of the last dose of a checkpoint inhibitor.

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 · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingPlasma protein binding is approximately 96% and is independent of drug serum concentration.
Pharmacodynamics · 1 Eintrag

Capmatinib inhibits the overactivity of c-Met, a receptor tyrosine kinase encoded by the _MET_ proto-oncogene. Mutations in _MET_ are involved in the proliferation of many cancers, including non-small cell lung cancer (NSCLC). Capmatinib may cause photosensitivity reactions in patients following ultraviolet (UV) exposure - patients undergoing therapy with capmatinib should be advised to use sunscreen and protective clothing to limit exposure to UV radiation. Instances of interstitial lung disease/pneumonitis, which can be fatal, occurred in patients being treated with capmatinib. Patients presenting with signs or symptoms of lung disease (e.g. cough, dyspnea, fever) should have capmatinib immediately withheld, and capmatinib should be permanently discontinued if no other feasible causes of the lung-related symptoms are identified.

Mechanism of Action · 1 Eintrag

Aberrant activation of c-Met has been documented in many cancers, including non-small cell lung cancer (NSCLC). Mutations that result in the skipping of _MET_ exon 14 lead to the formation of a mutant c-Met with a missing regulatory domain - these mutant proteins have a reduced ability to negatively regulate, leading to a pathological increase in their downstream activity. Capmatinib inhibits the phosphorylation of both wild-type and mutant variants of c-Met triggered by the binding of its endogenous ligand, hepatocyte growth factor - in doing so, it prevents c-Met-mediated phosphorylation of downstream signaling proteins, as well as the proliferation and survival of c-Met-dependent tumor cells.

Biological Half-LifeThe elimination half-life is 6.5 hours.
Metabolism/MetabolitesCapmatinib undergoes metabolism primarily via CYP3A4 and aldehyde oxidase. Specific biotransformation pathways and metabolic products have yet to be elucidated.
Anwendungen · 2 Einträge

BeschreibungCapmatinib is a competitive inhibitor with very potent and selective activity against MET compared to other kinases.

Verwenden2-Fluoro-N-methyl-4-(7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl)benzamide is used in the preparation of a combination formulation with allosteric SHP2 inhibitor TNO155. Used in treatment of non-small cell lung cancer with specific mutations (those that lead to mesenchymal-epithelial transition or MET exon 14 skipping).

Anbieter100 Anbieter

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海波以尔化工有限公司[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]

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