CHEBI:90951 - lumacaftor

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ChEBI Name lumacaftor
ChEBI ID CHEBI:90951
Definition An aromatic amide obtained by formal condensation of the carboxy group of 1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxylic acid with the aromatic amino group of 3-(6-amino-3-methylpyridin-2-yl)benzoic acid. Used for the treatment of cystic fibrosis.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H18F2N2O5
Net Charge 0
Average Mass 452.408
Monoisotopic Mass 452.118
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)
InChIKey UFSKUSARDNFIRC-UHFFFAOYSA-N
SMILES C1(C(NC2=CC=C(C(=N2)C3=CC(=CC=C3)C(O)=O)C)=O)(C4=CC5=C(C=C4)OC(O5)(F)F)CC1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): CFTR potentiator
A membrane transport modulator that restores the chloride ion transport ability of defective cystic fibrosis transmembrane conductance regulator (CFTR) genes.
Application(s): orphan drug
Any drug that has been developed specifically for treatment of a rare medical condition, the condition itself being known as an orphan disease.
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ChEBI Ontology
Outgoing lumacaftor (CHEBI:90951) has role CFTR potentiator (CHEBI:66902)
lumacaftor (CHEBI:90951) has role orphan drug (CHEBI:71031)
lumacaftor (CHEBI:90951) is a aromatic amide (CHEBI:62733)
lumacaftor (CHEBI:90951) is a benzodioxoles (CHEBI:38298)
lumacaftor (CHEBI:90951) is a benzoic acids (CHEBI:22723)
lumacaftor (CHEBI:90951) is a cyclopropanes (CHEBI:51454)
lumacaftor (CHEBI:90951) is a organofluorine compound (CHEBI:37143)
lumacaftor (CHEBI:90951) is a pyridines (CHEBI:26421)
Incoming Orkambi (CHEBI:90950) has part lumacaftor (CHEBI:90951)
IUPAC Name
3-(6-{[1-(2,2-difluoro-2H-1,3-benzodioxol-5-yl)cyclopropane-1-carbonyl]amino}-3-methylpyridin-2-yl)benzoic acid
INN Source
lumacaftor ChemIDplus
Synonyms Sources
VRT 826809 ChemIDplus
VRT-826809 ChemIDplus
VX 809 ChemIDplus
VX-809 ChemIDplus
Database Links Databases
5010 DrugCentral
D10134 KEGG DRUG
Lumacaftor Wikipedia
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Registry Numbers Types Sources
12892616 Reaxys Registry Number Reaxys
936727-05-8 CAS Registry Number ChemIDplus
936727-05-8 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
24771136 PubMed citation Europe PMC
24973281 PubMed citation Europe PMC
25981758 PubMed citation Europe PMC
26071414 PubMed citation Europe PMC
26416827 PubMed citation Europe PMC
26417173 PubMed citation Europe PMC
26492939 PubMed citation Europe PMC
26506855 PubMed citation Europe PMC
26510034 PubMed citation Europe PMC
26510035 PubMed citation Europe PMC
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26718821 PubMed citation Europe PMC
Last Modified
22 February 2017