IVACAFTOR

Search structure
Trade Names:
Synonyms:
Status: Approved (2012)
Entry Type: Small molecule
Molecule Category: Parent
ATC: R07AX02
UNII: 1Y740ILL1Z

Structure
InChI Key PURKAOJPTOLRMP-UHFFFAOYSA-N
Smile CC(C)(C)c1cc(C(C)(C)C)c(NC(=O)c2c[nH]c3ccccc3c2=O)cc1O
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H28N2O3
Molecular Weight 392.5
AlogP 5.08
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 82.19
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
POSITIVE MODULATOR Cystic fibrosis transmembrane conductance regulator positive modulator DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Other ion channel Chloride channel Cystic fibrosis transmembrane conductance regulator
3-1300 - - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Cystic Fibrosis 4 D003550 ClinicalTrials
Bronchitis, Chronic 2 D029481 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Kartagener Syndrome 2 D007619 ClinicalTrials
Liver Diseases 1 D008107 ClinicalTrials
Sinusitis 0 D012852 ClinicalTrials

Related Entries

Scaffolds

Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Headache 23.9
Gastrointestinal disorders Oropharyngeal pain 22.0
Infections and infestations Upper respiratory tract infection 22.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 20.2
Gastrointestinal disorders Oropharyngeal pain
Nervous system disorders Headache 17.0
Nervous system disorders Headache
Respiratory, thoracic and mediastinal disorders Nasal congestion 16.0
Infections and infestations Upper respiratory tract infection 16.0
Gastrointestinal disorders Abdominal pain 15.6
Gastrointestinal disorders Gastrointestinal pain 15.6
Respiratory, thoracic and mediastinal disorders Nasal congestion
Infections and infestations Nasopharyngitis 14.7
Infections and infestations Upper respiratory tract infection
Skin and subcutaneous tissue disorders Dermatitis 12.8
Gastrointestinal disorders Diarrhoea 12.8
Skin and subcutaneous tissue disorders Rash 12.8
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Nausea 11.9
Infections and infestations Nasopharyngitis
Gastrointestinal disorders Nausea
Skin and subcutaneous tissue disorders Dermatitis 10.0
Gastrointestinal disorders Nausea 10.0
Skin and subcutaneous tissue disorders Rash 10.0
Gastrointestinal disorders Diarrhoea
Cardiac disorders Dizziness 9.17
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Rash
Infections and infestations Rhinitis 6.0
Musculoskeletal and connective tissue disorders Arthralgia 5.0
Cardiac disorders Dizziness 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Cardiac disorders Dizziness

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Respiratory, thoracic and mediastinal disorders
21.91
Infections and infestations
16.48
Gastrointestinal disorders
9.92
General disorders and administration site conditions
8.63
Investigations
6.71
Nervous system disorders
4.67
Surgical and medical procedures
4.03
Cardiac disorders
3.64
Injury, poisoning and procedural complications
3.54
Skin and subcutaneous tissue disorders
3.05
Psychiatric disorders
2.92
Vascular disorders
2.77

Cross References

Resources Reference
CAS NUMBER 873054-44-5
ChEBI 66901
ChEMBL CHEMBL2010601
DrugBank DB08820
DrugCentral 4228
EPA CompTox DTXSID00236281
FDA SRS 1Y740ILL1Z
Human Metabolome Database HMDB0015705
Guide to Pharmacology 4342
PDB VX7
PharmGKB PA165950341
PubChem 16220172
SureChEMBL SCHEMBL351373
ZINC ZINC000052509463
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