Ivacaftor

HCID 16220172

Basic information

CAS
873054-44-5
Standard SMILES
CC(C)(C)c1cc(C(C)(C)C)c(NC(=O)c2c[nH]c3ccccc3c2=O)cc1O
InChIKey
PURKAOJPTOLRMP-UHFFFAOYSA-N
Molecular formula
C24H28N2O3
Average molar mass
392.5 g/mol
Monoisotopic mass
392.20999276

Overview

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.

Names & identifiers

Preferred name
Ivacaftor
IUPAC
N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1H-quinoline-3-carboxamide
English name
Ivacaftor
Molecular formula
C24H28N2O3
Molecular weight
392.49

Names & synonyms

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
Show more names
N-(2,4-DITERT-BUTYL-5-HYDROXYPHENYL)-4-OXO-1H-QUINOLINE-3-CARBOXAMIDEIvacaftor (VX-770)N-[2,4-Bis(tert-butyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-3-quinolinecarboxamide Ivacaftor (VX-770)CS-1914IvacatoEvacaftorIvacaftor-D4
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

Database identifiers

CAS
873054-44-5
PubChem CID
16220172
DTXSID
DTXSID00236281
ChEMBL
CHEMBL2010601
ChEBI
CHEBI:66901
UNII
1Y740ILL1Z
EC Number
800-027-5
Nikkaji
J3.163.539J

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
78.4 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
29

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Solubility · 2 items

low (<0.05 µg/mL)

2.00e-03 g/L

Human Drugs · 4 items

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

Physicochemical properties

Melting point
212 · 212-215°C
Boiling point
550.4 · 550.4±50.0 °C(Predicted)
Density
1.187 · 1.187
storage temp.
Refrigerator
solubility
DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka
11.08 · 11.08±0.23(Predicted)

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

Toxicology

Drug Induced Liver Injury · 6 items

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

Safety data

wgk
WGK 3
hs_code
29333990
Signal word
Warning
Symbol(GHS)
GHS08,GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H361-H319-H315-H335

Chemistry & industry

Pharmacology

ATC Code · 3 items

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 item

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 item

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.

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 item

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.

Applications · 3 items

DescriptionIn January 2012, the US FDA approved ivacaftor for the treatment of cystic fibrosis (CF) in patients who have the G551D mutation of the CF transmembrane regulator (CFTR) and are at least 6 years old. Ivacaftor (also known as VX-770) is a CFTR potentiator that increases the open probability of CFTR, thus increasing chloride secretion particularly in the 5% of CF patients with the G551D/F508 gating/ processing mutation. Ivacaftor was discovered by medicinal chemistry optimization of a lead scaffold identified through high-throughput screening of a 228,000 compound collection. In cultured bronchial epithelial cells from a CF patient with F508del, ivacaftor increased chloride secretion (EC50=81 nM). Preparation of ivacaftor is accomplished via a multistep synthesis oftwointermediates, 4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 5-amino-di-tert-butylphenyl methyl carbonate, which are coupled using propane phosphonic acid anhydride (T3P) to afford the amide; deprotection of the phenol then provides ivacaftor.

UsesIvacaftor is used in the treatment of cystic fibrosis.

UsesIvacaftor (VX-770, Kalydeco) is a potentiator of CFTR targeting G551D-CFTR and F508del-CFTR with EC50 of 100 nM and 25 nM, respectively

Upstream & downstream products

Upstream raw materials

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海欧堃化学有限公司(QQ 39130253)021-68712331 39130253 · [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]
上海沸柏化工科技有限公司021-58955608,2250286 15921236618 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

18 records

Compound notes

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