Compound: Ivacaftor
SMILES: O=c1c(C(=O)Nc2c(cc(C(C)(C)C)c(c2)O)C(C)(C)C)c[nH]c3c1cccc3
InChIKey: PURKAOJPTOLRMP-UHFFFAOYSA-N
Synonyms: Ivacaftor, 873054-44-5, VX-770, Kalydeco, N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide, ivacaftorum, 1Y740ILL1Z, CHEBI:66901, DTXSID00236281, ORKAMBI COMPONENT IVACAFTOR, SYMKEVI COMPONENT IVACAFTOR, TRIKAFTA COMPONENT IVACAFTOR, 3-Quinolinecarboxamide, N-(2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl)-1,4-dihydro-4-oxo-, 3-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-carboxamide, N-[2,4-Bis(1,1-dimethylethyl)-5-hydroxyphenyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide, RefChem:58494, DTXCID00158772, R07AX02, Elexacaftor, Tezacaftor, and Ivacaftor, 800-027-5, Ivacaftor (VX-770), N-[2,4-Bis(tert-butyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxo-3-quinolinecarboxamide, VX 770, Ivacaftor-d18, 1413431-05-6, MFCD17171361, N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1H-quinoline-3-carboxamide, s1144, Ivacaftor (4-tertbutyl-d9) (Major), Kalydeco (TN), Ivacaftor [USAN], Ivacaftor [USAN:INN], UNII-1Y740ILL1Z, VX7, IVACAFTOR [INN], IVACAFTOR [MI], Ivacaftor (USAN/INN), IVACAFTOR [VANDF], IVACAFTOR [WHO-DD], MLS006011119, SCHEMBL351373, SCHEMBL417309, GTPL4342, orb1305294, IVACAFTOR [ORANGE BOOK], VX-770, Ivacaftor, Kalydeco, CHEMBL2010601, SCHEMBL29357389, SCHEMBL29379239, EX-A441, PURKAOJPTOLRMP-UHFFFAOYSA-N, HMS3654E10, HMS3744K05, HMS5079A11, NGC43107, BDBM50032693, EBC-11412, AKOS015994762, AKOS032950001, N-(2,4-ditert-butyl-5-hydroxy-phenyl)-4-oxo-1H-quinoline-3-carboxamide, CCG-268562, CS-0497, DB08820, EX-7211, LE-0002, SB16815, compound 48 [PMID: 25441013], NCGC00242480-01, NCGC00242480-03, AC-28324, DA-54489, FI143182, HY-13017, SMR004702900, SY067891, NS00009974, SW219620-1, D09916, AB01565806_02, EN300-7400944, F468426, Q6095693, BRD-K52818472-001-02-2, Z2146566713, Cystic Fibrosis Transmembrane Conductance Regulator Potentiator, N-(5-hydroxy-2,4-ditert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide, N-(2,4-ditert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide, N-(5-Hydroxy-2,4-bis(2-methyl-2-propanyl)phenyl]-4-oxo-1,4-dihydro-3-quinolinecarboxamide, N-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide, 1134822-00-6
Theoretical properties:
molecular_formula: C24H28N2O3
molecular_weight: 392.5 g/mol
exact_mass: 392.20999276 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 29
topological_polar_surface_area: 78.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 212-215
solubility: low (<0.05 µg/mL)
Descriptions:
{"pubchem": "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.", "chebi": "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-<em>tert</em>-butylphenol. Used for the treatment of cystic fibrosis.", "chembl": "IVACAFTOR is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Ivacaftor is a medication used to treat cystic fibrosis in people with certain mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) gene (primarily the G551D mutation), who account for 4\u20135% cases of cystic fibrosis. It is also included in combination medications, lumacaftor/ivacaftor, tezacaftor/ivacaftor, and elexacaftor/tezacaftor/ivacaftor which are used to treat people with cystic fibrosis.\nIvacaftor was approved by the US Food and Drug Administration (FDA) in January 2012. The combination drug lumacaftor/ivacaftor was approved by the FDA in July 2015. Ivacaftor, and the combination elexacaftor/tezacaftor/ivacaftor, are both on the World Health Organization's List of Essential Medicines.\nCystic fibrosis is caused by any one of several defects in the CFTR protein, which regulates fluid flow within cells and affects the components of sweat, digestive fluids, and mucus. One such defect is the G551D mutation, in which the amino acid glycine (G) in position 551 is replaced with aspartic acid (D).  G551D is characterized by a dysfunctional CFTR protein on the cell surface.  In the case of G551D, the protein is trafficked to the correct area, the epithelial cell surface, but once there the protein  cannot transport chloride through the channel. Ivacaftor, a CFTR potentiator, improves the transport of chloride through the ion channel by binding to the channels directly to induce a non-conventional mode of gating which in turn increases the probability that the channel is open.\n\n"}