LUMACAFTOR

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Search structure


Synonyms	Lumacaftor VRT 826809 VRT-826809 VX 809 VX-809
Status
Molecule Category	Free-form
UNII	EGP8L81APK
EPA CompTox	DTXSID30239523


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	UFSKUSARDNFIRC-UHFFFAOYSA-N
Smiles	Cc1ccc(NC(=O)C2(c3ccc4c(c3)OC(F)(F)O4)CC2)nc1-c1cccc(C(=O)O)c1
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C24H18F2N2O5
Molecular Weight	452.41
AlogP	4.75
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	5.0
Polar Surface Area	97.75
Molecular species	ACID
Aromatic Rings	3.0
Heavy Atoms	33.0

Bioactivity

Mechanism of Action	Action	Reference
Cystic fibrosis transmembrane conductance regulator stabiliser	STABILISER	FDA


Protein: Cystic fibrosis transmembrane conductance regulator Description: Cystic fibrosis transmembrane conductance regulator Organism : Homo sapiens P13569 ENSG00000001626

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8	-	12000	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9	-	32000	-	-	-
Ion channel Other ion channel Chloride channel Cystic fibrosis transmembrane conductance regulator	2570-2600	-	72800	-	-

Assay Description	Organism	Bioactivity	Reference
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	37.26 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	14.17 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.625 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.02 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.02 %

Cross References

Resources	Reference
ChEBI	90951
ChEMBL	CHEMBL2103870
DrugBank	DB09280
DrugCentral	5010
FDA SRS	EGP8L81APK
Guide to Pharmacology	7481
PharmGKB	PA166114483
PubChem	16678941
SureChEMBL	SCHEMBL377028
ZINC	ZINC000064033452

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).