lumacaftor   Click here for help

GtoPdb Ligand ID: 7481

Synonyms: VRT-826809 | VX-809 | VX809
Approved drug PDB Ligand
lumacaftor is an approved drug (EMA & FDA (2015))
Compound class: Synthetic organic
Comment: Lumacaftor is termed a cystic fibrosis transmembrane conductance regulator (CFTR) corrector, acting to reduce mis-folding of the defective F508del mutant CFTR protein, in comparison to ivacaftor which is termed a CFTR potentiator drug. The F508del mutation is the most common cause of cystic fibrosis and accounts for approximately 60% of CF patients in Europe. Cryo-electron microscopy of CFTR-lumacaftor complexes provided insight into how the correctors operate at the molecular level, with the findings published in early 2022 by Fiedorczuk and Chen [1].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: lumacaftor

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 97.75
Molecular weight 452.12
XLogP 4.93
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES O=C(C1(CC1)c1ccc2c(c1)OC(O2)(F)F)Nc1ccc(c(n1)c1cccc(c1)C(=O)O)C
Isomeric SMILES O=C(C1(CC1)c1ccc2c(c1)OC(O2)(F)F)Nc1ccc(c(n1)c1cccc(c1)C(=O)O)C
InChI InChI=1S/C24H18F2N2O5/c1-13-5-8-19(27-20(13)14-3-2-4-15(11-14)21(29)30)28-22(31)23(9-10-23)16-6-7-17-18(12-16)33-24(25,26)32-17/h2-8,11-12H,9-10H2,1H3,(H,29,30)(H,27,28,31)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2015))
IUPAC Name Click here for help
3-[6-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3-methylpyridin-2-yl]benzoic acid
International Nonproprietary Names Click here for help
INN number INN
9449 lumacaftor
Synonyms Click here for help
VRT-826809 | VX-809 | VX809
Database Links Click here for help
CAS Registry No. 936727-05-8
ChEMBL Ligand CHEMBL2103870
DrugCentral Ligand 5010
GtoPdb PubChem SID 187051784
PubChem CID 16678941
Search Google for chemical match using the InChIKey UFSKUSARDNFIRC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UFSKUSARDNFIRC
Search PubMed clinical trials lumacaftor
Search PubMed titles lumacaftor
Search PubMed titles/abstracts lumacaftor
UniChem Compound Search for chemical match using the InChIKey UFSKUSARDNFIRC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UFSKUSARDNFIRC-UHFFFAOYSA-N
Wikipedia Lumacaftor