StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

Binimetinib

HCID 10288191
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
606143-89-9
Standard-SMILES
Cn1cnc2c(F)c(Nc3ccc(Br)cc3F)c(C(=O)NOCCO)cc21
InChIKey
ACWZRVQXLIRSDF-UHFFFAOYSA-N
Summenformel
C17H15BrF2N4O3
Durchschnittliche Molmasse
441,2 g/mol
Monoisotopische Masse
440,02956

Überblick

Binimetinib is a member of the class of benzimidazoles that is 1-methyl-1H-benzimidazole which is substituted at positions 4, 5, and 6 by fluorine, (4-bromo-2-fluorophenyl)nitrilo, and N-(2-hydroxyethoxy)aminocarbonyl groups, respectively. It is a MEK1 and MEK2 inhibitor (IC50= 12 nM). Approved by the FDA for the treatment of patients with unresectable or metastatic melanoma with a BRAF V600E or V600K mutation in combination with encorafenib. It has a role as an antineoplastic agent, an apoptosis inducer and an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor. It is a member of benzimidazoles, a member of bromobenzenes, a secondary amino compound, a hydroxamic acid ester and a member of monofluorobenzenes.

Namen und Bezeichner

Bevorzugter Name
Binimetinib
IUPAC
6-(4-bromo-2-fluoroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
Englischer Name
Binimetinib
Summenformel
C17H15BrF2N4O3
Molmasse
441.23

Namen und Synonyme

Binimetinib606143-89-9MEK162ARRY-162MektoviMEK-162ARRY-4381625-[(4-Bromo-2-fluorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzimidazole-6-carboxamideNVP-MEK162ARRY 438162binimetinibumDTXSID70209422
Weitere Namen anzeigen
CS-394ARRY 162MEK162, ARRY-162Valine Impurity 34MEK162(Binimetinib)MEK162 (ARRY-438162)
181R97MR71CHEBI:1453715-[(4-bromo-2-fluorophenyl)amino]-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-1,3-benzodiazole-6-carboxamide6-[(4-bromo-2-fluorophenyl)amino]-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-1,3-benzodiazole-6-carboxamide5-((4-BROMO-2-FLUOROPHENYL)AMINO)-4-FLUORO-N-(2-HYDROXYETHOXY)-1-METHYL-1H-BENZIMIDAZOLE-6-CARBOXAMIDE6-((4-bromo-2-fluorophenyl)amino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamideRefChem:58059

Datenbank-Bezeichner

CAS
606143-89-9
PubChem CID
10288191

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,1
Polarare Oberfläche (TPSA)
88,4 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
6
Schwere Atome
27
Formalladung
0
Komplexität
521

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents

Pharmaceuticals -> Listed in ZINC15

Human Drugs · 4 Einträge

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

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
203 oC · >203oC (dec.)
Dichte
1.67 · 1.67
storage temp.
-20 °C · -20°C
Löslichkeit
Soluble in DMSO (up to at least 25 mg/ml)
pka
14.2 · 14.20±0.10(Predicted)
Aggregatzustand
solid
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.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 92.5% (37 of 40) of all reports.

Not Classified

Aggregated GHS information provided per 40 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationREACH registered substance: 5-(4-bromo-2-fluoroanilino)-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzimidazole-6-carboxamide (EC: 639-995-7)
Hazard Classes and CategoriesNot Classified

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Binimetinib

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

hs_code
2933998090

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein BindingBinimetinib is 97% bound to human plasma proteins and the blood-to-plasma ratio is 0.72.
Pharmacodynamics · 1 Eintrag

In vitro, binimetinib inhibited extracellular signal-related kinase (ERK) phosphorylation in cell-free assays as well as viability and MEK-dependent phosphorylation of BRAF-mutant human melanoma cell lines. Binimetinib also inhibited in vivo ERK phosphorylation and tumor growth in BRAF-mutant murine xenograft models. MEK is an enzyme that regulates the biosynthesis of inflammatory cytokines such as TNF, IL-6 and IL-1; therefore, binimetinib anti-tumor activity can be mediated through the interference of cytokines biosynthesis. Binimetinib and [encorafenib] target two different kinases in the RAS/RAF/MEK/ERK pathway. Compared to either drug alone, coadministration of [encorafenib] and binimetinib resulted in greater anti-proliferative activity in vitro in BRAF mutation-positive cell lines and greater anti-tumor activity with respect to tumor growth inhibition in BRAF V600E mutant human melanoma xenograft studies in mice. Additionally, the combination of binimetinib and [encorafenib] delayed the emergence of resistance in BRAF V600E mutant human melanoma xenografts in mice compared to either drug alone. In a BRAF V600E mutant NSCLC patient-derived xenograft model in mice, coadministration of [encorafenib] and binimetinib resulted in greater anti-tumor activity compared to binimetinib alone, with respect to tumor growth inhibition. Increased tumor growth delay after dosing cessation was also observed with the coadministration compared to either drug alone. Following MEKTOVI 45 mg twice daily, no clinically meaningful QT prolongation was observed.

Mechanism of Action · 1 Eintrag

Binimetinib, noncompetitive with ATP, binds reversibly to and inhibits the activity of mitogen-activated extracellular signal-regulated kinase (MEK) 1 and 2. The inhibition of MEK1/2 prevents the activation of MEK1/2-dependent effector proteins and transcription factors, resulting in the inhibition of growth factor-mediated cell signaling such as the downstream extracellular signal-related kinase (ERK) pathway. This may lead to the inhibition of tumor cell proliferation and an inhibition in the production of various inflammatory cytokines including interleukin-1, -6, and tumor necrosis factor. MEK1/2 are themselves threonine and tyrosine kinases that possess a dual specificity. They subsequently contribute critically to the activation of the RAS/RAF/MEK/ERK pathway and are typically upregulated in a number of different tumor cell types.

Zugehörige Reaktionen

2
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 591120
HRID 591120als Produktuspto-grants-2016_01
Reaktionsgleichung von HRID 1048839
HRID 1048839als Produktuspto-grants-2016_07

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID
DTXSID70209422
ChEMBL
CHEMBL3187723
ChEBI
CHEBI:145371
UNII
181R97MR71
EC Number
639-995-7
Nikkaji
J3.336.515B
InChI
InChI=1S/C17H15BrF2N4O3/c1-24-8-21-16-13(24)7-10(17(26)23-27-5-4-25)15(14(16)20)22-12-3-2-9(18)6-11(12)19/h2-3,6-8,22,25H,4-5H2,1H3,(H,23,26)
InChIKey
ACWZRVQXLIRSDF-UHFFFAOYSA-N
SMILES
C1N(C)C2=CC(C(NOCCO)=O)=C(NC3=CC=C(Br)C=C3F)C(F)=C2N=1
Biological Half-LifeThe mean (CV%) terminal half-life (t1/2) of binimetinib is 3.5 hours (28.5%).
Metabolism/Metabolites · 1 Eintrag

The primary metabolic pathway is glucuronidation with UGT1A1 contributing up to 61% of the binimetinib metabolism. Other pathways of binimetinib metabolism include N-dealkylation, amide hydrolysis, and loss of ethane-diol from the side chain. The active metabolite M3 produced by CYP1A2 and CYP2C19 represents 8.6% of the binimetinib exposure. Following a single oral dose of 45 mg radiolabeled binimetinib, approximately 60% of the circulating radioactivity AUC in plasma was attributable to binimetinib.

Absorption, Distribution and Excretion · 4 Einträge

The pharmacokinetics of binimetinib was studied in healthy subjects and patients with solid tumors. After twice-daily dosing, the accumulation is 1.5-fold and the coefficient of variation (CV%) of the area under the concentration-time curve (AUC) is <40% at steady state. The systemic exposure of binimetinib is approximately dose proportional. After oral administration, at least 50% of the binimetinib dose was absorbed with a median time to maximum concentration (Tmax) of 1.6 hours. The administration of a single dose of binimetinib 45 mg with a high-fat, high-calorie meal (consisting of approximately 150 calories from protein, 350 calories from carbohydrate, and 500 calories from fat) in healthy subjects had no effect on binimetinib exposure.

Following a single oral dose of 45 mg radiolabeled binimetinib in healthy subjects, 62% (32% unchanged) of the administered dose was recovered in the feces while 31% (6.5% unchanged) was recovered in the urine.

The geometric mean (CV%) of the apparent volume of distribution of binimetinib is 92 L (45%).

The apparent clearance (CL/F) of binimetinib is is 20.2 L/h (24%).

Anwendungen

VerwendenMEK 162 is a MEK1/2 inhibitor allowing it to be a effective anti-cancer medication.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

methyl 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1H-benzo[d]imidazole-6-carboxylate4-Bromo-2-fluoro-1-iodobenzene(5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazol-6-yl)(1H-imidazol-1-yl)methanonepotassium 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylateMethyl 5-aMino-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylateMethyl 4-aMino-3-fluoro-2-((2-fluorophenyl)aMino)-5-nitrobenzoateMethyl 4-amino-2,3-difluoro-5-nitrobenzoate5-((4-broMo-2-fluorophenyl)aMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylic acid5-((4-bromo-2-fluorophenyl)amino)-N-(2-(tert-butoxy)ethoxy)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxamide2-Fluoranilin

Anbieter100 Anbieter

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
上海策嵘生物科技有限公司[email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
江苏南创化学与生命健康研究院有限公司15720605021 · [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]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
Advanced chemblocks inc650-6922368 650-6922368;650-6922368 · [email protected]
武汉瑞立升科技发展有限公司27-027-83314682 13554138826 · [email protected]
学研惠(武汉)科技有限公司15727060112 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
济南精合医药科技有限公司0531-88811783 · [email protected]
大赛璐药物手性技术(上海)有限公司021-50460086-9 15921403865 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
南京世洲生物科技有限公司13675144456 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
北京奥秘佳得医药科技有限公司+86-13522808617 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
广州市慈铭生物科技有限公司020-38082199,29065168,38082986,29878298,29866629,4000192398
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
上海楼岚生物科技有限公司021-52996696,15000506266 15000506266
上海泽涵生物医药科技有限公司021-61350663 13052117465 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
斯派螺(武汉)药物研发有限公司[email protected]
Hangzhou Proserre Chemical Co.,Ltd.+86-571-86088112 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
上海德欣致远生物技术有限公司021-58088081 18317173152 · [email protected]
上海润栖医药科技有限公司021-38751876 15000076078 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
武汉市承天精细化工有限公司18164098996 · [email protected]
Target molecule Corp.857-239-0968 · [email protected]
上海珀法姆医药科技有限公司+86 18721201413 · [email protected]
沧州恩科医药科技有限公司0317-5296180 15533709196 · [email protected]
成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
成都同创源医药科技有限公司028-83379370 13880556291 · [email protected]