ivacaftor   

GtoPdb Ligand ID: 4342

Synonyms: Kalydeco® | VX-770
ivacaftor is an approved drug (FDA and EMA (2012))
Compound class: Synthetic organic
Comment: Ivacaftor is a cystic fibrosis transmembrane conductance regulator (CFTR) potentiator, the net effect of which is increased chloride channel opening.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: ivacaftor

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 82.19
Molecular weight 392.21
XLogP 6.93
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(c1c[nH]c2c(c1=O)cccc2)Nc1cc(O)c(cc1C(C)(C)C)C(C)(C)C
Isomeric SMILES O=C(c1c[nH]c2c(c1=O)cccc2)Nc1cc(O)c(cc1C(C)(C)C)C(C)(C)C
InChI InChI=1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)
InChI Key PURKAOJPTOLRMP-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA and EMA (2012))
IUPAC Name
N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
International Nonproprietary Names
INN number INN
9263 ivacaftor
Synonyms
Kalydeco® | VX-770
Database Links
CAS Registry No. 873054-44-5
ChEBI CHEBI:66901
ChEMBL Ligand CHEMBL2010601
DrugBank Ligand DB08820
DrugCentral Ligand 4228
GtoPdb PubChem SID 178101159
PubChem CID 16220172
RCSB PDB Ligand VX7
Search Google for chemical match using the InChIKey PURKAOJPTOLRMP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PURKAOJPTOLRMP
Search PubMed clinical trials ivacaftor
Search PubMed titles ivacaftor
Search PubMed titles/abstracts ivacaftor
Search UniChem for chemical match using the InChIKey PURKAOJPTOLRMP-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone PURKAOJPTOLRMP
Wikipedia Ivacaftor