ivacaftor   Click here for help

GtoPdb Ligand ID: 4342

Synonyms: Kalydeco® | VX-770
Approved drug PDB Ligand
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.
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View more information in the IUPHAR Pharmacology Education Project: ivacaftor

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA and EMA (2012))
IUPAC Name Click here for help
N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9263 ivacaftor
Synonyms Click here for help
Kalydeco® | VX-770
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-5678956
Reactome Reaction Reactome logo R-HSA-5678992, R-HSA-5679000
Other databases
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
UniChem Compound Search for chemical match using the InChIKey PURKAOJPTOLRMP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PURKAOJPTOLRMP-UHFFFAOYSA-N
Wikipedia Ivacaftor