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Ivacaftor

HCID 178798247
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Grundinformationen

CAS
1413431-22-7
Standard-SMILES
CC(C)(C)c1cc(C(C)(C)C)c(NC(=O)c2c[nH]c3ccccc3c2=O)cc1O
InChIKey
PURKAOJPTOLRMP-UHFFFAOYSA-N
Summenformel
C24H28N2O3
Durchschnittliche Molmasse
392,5 g/mol

Überblick

Ivacaftor is an aromatic amide obtained by formal condensation of the carboxy group of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid with the amino group of 5-amino-2,4-di-tert-butylphenol. Used for the treatment of cystic fibrosis. It has a role as a CFTR potentiator and an orphan drug. It is a quinolone, a monocarboxylic acid amide, a member of phenols and an aromatic amide.

Namen und Bezeichner

Bevorzugter Name
Ivacaftor
IUPAC
N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1H-quinoline-3-carboxamide
Englischer Name
Ivacaftor-d19
Summenformel
C24H28N2O3
Molmasse
392.5

Namen und Synonyme

Ivacaftor873054-44-5VX-770KalydecoN-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamideivacaftorum1Y740ILL1ZCHEBI:669013-Quinolinecarboxamide, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-DTXSID00236281ORKAMBI COMPONENT IVACAFTORSYMKEVI COMPONENT IVACAFTOR
Weitere Namen anzeigen
Ivacaftor-d19Ivacaftor-D19Q: What is Ivacaftor-D19 Q: What is the CAS Number of Ivacaftor-D19N-[2,4-bis[1,1-di(methyl-d3)ethyl-2,2,2-d3]-5-hydroxyphenyl-3d]-1,4-dihydro-4-oxo-3-quinolinecarboxamide
TRIKAFTA COMPONENT IVACAFTOR3-Quinolinecarboxamide, N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-1,4-dihydro-4-oxo-N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamideN-[2,4-Bis(1,1-dimethylethyl)-5-hydroxyphenyl]-4-oxo-1,4-dihydroquinoline-3-carboxamideRefChem:58494DTXCID00158772R07AX02Elexacaftor, Tezacaftor, and Ivacaftor

Datenbank-Bezeichner

CAS
1413431-22-7

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
78,4 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
4
Schwere Atome
29
Formalladung
0
Komplexität
671

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Solubility · 2 Einträge

low (<0.05 µg/mL)

2.00e-03 g/L

Human Drugs · 4 Einträge

Breast Feeding; Lactation; Milk, Human; Chloride Channel Agonists; Cystic Fibrosis Transmembrane Conductance Regulator Protein Modulator; CFTR Protein Modulator

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point212-215
Physical DescriptionSolid
Dissociation Constants11.08, 1.5

Physikochemische Eigenschaften

storage temp.

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 · 5 Einträge

This chemical does not meet GHS hazard criteria for 50% (3 of 6) of reports.

Warning

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Ivacaftor

vLess-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

R07AX30

R - Respiratory system

QR - Respiratory system

Protein BindingAbout 99% of ivacaftor is bound to plasma proteins, primarily to alpha 1-acid glycoprotein and albumin.
Pharmacodynamics · 1 Eintrag

The use of Ivacaftor has been shown to both improve CF symptoms and modulate underlying disease pathology. This is achieved by potentiating the channel opening probability (or gating) of CFTR protein in patients with impaired gating mechanisms. This is in contrast to [DB09280], another CF medication, that functions by preventing misfolding of the CFTR protein and thereby results in increased processing and trafficking of mature protein to the cell surface. Results from clinical trials indicated that treatment with ivacaftor results in improved lung function, reduced chance of experiencing a pulmonary exacerbation, reduced sweat chloride, increased weight gain, and improvements in CF symptoms and quality of life. When combined with tezacaftor, significant improvements in lung function have been observed in clinical studies. Ivacaftor was not found to increase the QTc interval in a clinically significant manner. Although ivacaftor given alone has not shown any significant improvements in patients with the delta-F508 mutation, it has shown significant improvements (>10% increase in FEV1 from baseline) in lung function for the following mutations: E56K, P67L, R74W, D110E, D110H, R117C, R117H, G178R, E193K, L206W, R347H, R352Q, A455E, S549N, S549R, G551D, G551S, D579G, S945L, S977F, F1052V, K1060T, A1067T, G1069R, R1070Q, R1070W, F1074L, D1152H, G1244E, S1251N, S1255P, D1270N, and G1349. This list was expanded by the FDA in May 2017 from 10 to 33 to accommodate more rare mutations. It is important to note that this drug may cause an increase in liver transaminases (ALT, AST). Ensure to assess liver transaminases before the initiation of treatment, every 3 months during the first year of administration, followed by every year thereafter.

Mechanism of Action · 1 Eintrag

A wide variety of CFTR mutations correlate to the Cystic Fibrosis phenotype and are associated with differing levels of disease severity. The most common mutation, affecting approximately 70% of patients with CF worldwide, is known as F508del-CFTR or delta-F508 (ΔF508), in which a deletion in the amino acid phenylalanine at position 508 results in impaired production of the CFTR protein, thereby causing a significant reduction in the amount of ion transporter present on cell membranes. Ivacaftor as monotherapy has failed to show a benefit for patients with delta-F508 mutations, most likely due to an insufficient amount of protein available at the cell membrane for interaction and potentiation by the drug. The next most common mutation, G551D, affecting 4-5% of CF patients worldwide is characterized as a missense mutation, whereby there is sufficient amount of protein at the cell surface, but opening and closing mechanisms of the channel are altered. Ivacaftor is indicated for the management of CF in patients with this second type of mutation, as it binds to and potentiates the channel opening ability of CFTR proteins on the cell membrane. Ivacaftor exerts its effect by acting as a potentiator of the CFTR protein, an ion channel involved in the transport of chloride and sodium ions across cell membranes of the lungs, pancreas, and other organs. Alterations in the CFTR gene result in altered production, misfolding, or function of the protein and consequently abnormal fluid and ion transport across cell membranes. Ivacaftor improves CF symptoms and underlying disease pathology by potentiating the channel open probability (or gating) of CFTR protein in patients with impaired CFTR gating mechanisms. The overall level of ivacaftor-mediated CFTR chloride transport is dependent on the amount of CFTR protein at the cell surface and how responsive a particular mutant CFTR protein is to ivacaftor potentiation.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
ChEMBL
CHEMBL2010601
ChEBI
CHEBI:66901
UNII
1Y740ILL1Z
EC Number
800-027-5
Nikkaji
J3.163.539J
-20 °C · Store at -20°C
Löslichkeit
Acetonitrile:Methanol (1:1): soluble,DMSO: soluble
Aggregatzustand
A solid
Biological Half-LifeIn a clinical study, the apparent terminal half-life was approximately 12 hours following a single dose of ivacaftor. One source mentions the half-life ranges from 12 to 14 hours.
Metabolism/Metabolites · 1 Eintrag

Ivacaftor is extensively metabolized in humans. In vitro and clinical studies indicate that ivacaftor is primarily metabolized by CYP3A. From this metabolism, the major formed metabolites are M1 and M6. M1 is considered pharmacologically active even though it just presents approximately one-sixth the effect of the parent compound ivacaftor. On the other hand, M6 is not considered pharmacologically active as it represents less than one-fiftieth of the effect of the parent compound.

FDA Pharmacological Classification · 6 Einträge

1Y740ILL1Z

IVACAFTOR

Established Pharmacologic Class [EPC] - Cystic Fibrosis Transmembrane Conductance Regulator Potentiator

Mechanisms of Action [MoA] - Chloride Channel Activation Potentiators

Mechanisms of Action [MoA] - Cytochrome P450 2C9 Inhibitors

Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors

MeSH Pharmacological ClassificationA class of drugs that stimulate chloride ion influx through cell membrane channels.
Absorption, Distribution and Excretion · 4 Einträge

Ivacaftor is well absorbed in the gastrointestinal tract. Following administration of ivacaftor with fat-containing foods, peak plasma concentrations were reached at 4 hours (Tmax) with a maximum concentration (Cmax) of 768 ng/mL and AUC of 10600 ng * hr/mL. It is recommended that ivacaftor is taken with fat-containing foods as they increase absorption by approximately 2.5- to 4-fold.

After oral administration, ivacaftor is mainly eliminated in the feces after metabolic conversion and this elimination represents 87.8% of the dose. From the total eliminated dose, the metabolites M1 and M6 account for the majority of the eliminated dose, being 22% for M1 and 43% for M6. Ivacaftor shows negligible urinary excretion as the unchanged drug.

After oral administration of 150 mg every 12 hours for 7 days to healthy volunteers in a fed state, the mean (±SD) for apparent volume of distribution was 353 (122) L.

The CL/F (SD) for the 150 mg dose was 17.3 (8.4) L/hr in healthy subjects.

Cellular LocationsMembrane
Anwendungen · 1 Eintrag

BeschreibungIvacaftor-d19 is intended for use as an internal standard for the quantification of ivacaftor by GC- or LC-MS. Ivacaftor is an orally bioavailable potentiator of the cystic fibrosis transmembrane conductance regulator (CFTR) that improves chloride transport. It increases the forskolin-induced CFTR-mediated epithelial current in cells expressing the G551D missense mutation associated with severe cystic fibrosis by approximately 4-fold (EC50 = 100 nM) but has no effect on current in the absence of forskolin. Ivacaftor increases chloride secretion in cultured human cystic fibrosis bronchial epithelial cells carrying the G551D mutation on one allele and the common ΔF508 processing mutation on the other allele. It binds CFTR directly and leads to CFTR channel opening via an ATP-independent mechanism. Formulations containing ivacaftor have been used in the treatment of cystic fibrosis in patients carrying one or more mutations in the CFTR gene.

Anbieter7 Anbieter

济南百隆化学有限公司[email protected] · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
山东大有药物研发有限公司[email protected] 15165037910 · [email protected]
上海稳同科技有限公司02151600108 13062666369 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
TLC梯尔希(南京)药物研发有限公司18012923235 · [email protected]