PRANLUKAST

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Synonyms
Status
Molecule Category UNKNOWN
ATC R03DC02
UNII TB8Z891092
EPA CompTox DTXSID3043782

Structure

InChI Key NBQKINXMPLXUET-UHFFFAOYSA-N
Smiles O=C(Nc1cccc2c(=O)cc(-c3nnn[nH]3)oc12)c1ccc(OCCCCc2ccccc2)cc1
InChI
InChI=1S/C27H23N5O4/c33-23-17-24(26-29-31-32-30-26)36-25-21(23)10-6-11-22(25)28-27(34)19-12-14-20(15-13-19)35-16-5-4-9-18-7-2-1-3-8-18/h1-3,6-8,10-15,17H,4-5,9,16H2,(H,28,34)(H,29,30,31,32)

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H23N5O4
Molecular Weight 481.51
AlogP 4.63
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 123.0
Molecular species ACID
Aromatic Rings 5.0
Heavy Atoms 36.0

Bioactivity

Mechanism of Action Action Reference
Cysteinyl leukotriene receptor 1 antagonist ANTAGONIST PubMed PubMed PubMed PubMed PubMed
Protein: Cysteinyl leukotriene receptor 1
Description: Cysteinyl leukotriene receptor 1
Organism : Homo sapiens
Q9Y271 ENSG00000173198
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 40
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family
- 7000-68000 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Leukotriene receptor
- 1-4 1 1-1 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group H Nuclear hormone receptor subfamily 1 group H member 4
15000 - - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 2970 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 2700 - - -
Assay Description Organism Bioactivity Reference
Binding affinity towards Cysteinyl leukotriene D4 receptor (cysLT1) was measured by the displacement of [3H]LTD4 radioligand Cavia porcellus 1.0 nM
Displacement of [3H]LTD4 from Cysteinyl leukotriene D4 receptor in guinea pig lung membranes Cavia porcellus 1.0 nM
In vitro binding of Cysteinyl leukotriene receptor 1 to guinea pig lung membranes Cavia porcellus 0.8 nM
Antagonism of Cysteinyl leukotriene receptor 1 from guinea pig lung membranes Cavia porcellus 0.8 nM
Inhibition of LTD4 (5 ng/site) induced vascular permeability in guinea pig skin at dose 0.3 mg/kg given perorally Cavia porcellus 74.7 %
Inhibition of LTD4 (5 ng/site) induced vascular permeability in guinea pig skin at dose 1 mg/kg given perorally Cavia porcellus 75.2 %
Inhibition of LTD4 induced increase of vascular permeability after injection of 10 ng/site at 1 uM intraperitoneally Cavia porcellus 100.0 %
Compound was tested for its ability to block antigen induced airway obstruction in guinea pig at dose 1 mg/kg at 1 hr Cavia porcellus 50.1 %
Inhibition of LTC4 induced smooth muscle contraction of guinea pig ileum Cavia porcellus 0.044 nM
Inhibition of ovalbumin-induced contraction (10 ng/mL) of guinea pig trachea at 10 uM. Cavia porcellus 80.0 %
Ability to antagonize LTD4 receptors isolated from guinea pig lung membranes Cavia porcellus 0.8 nM
In vitro blocking of extracellular calcium mobilization in human U937 cells Homo sapiens 1.0 nM
Compound was evaluated for influx of calcium mobilization in human U937 cells Homo sapiens 1.0 nM
Compound was tested for its ability to inhibit calcium influx in human U937 cells Homo sapiens 1.0 nM
Antagonist activity at CysLT1 receptor in human dU937 cells assessed as inhibition of LTD4-induced increase of calcium level treated 30 mins before LTD4 challenge Homo sapiens 0.8 nM
Antagonist activity at human CysLT1 Homo sapiens 4.3 nM
Displacement of [3H]ICI from cysteinyl leukotriene receptor 1 in Hartley guinea pig lung membrane after 30 mins by liquid scintillation counting method Cavia porcellus 0.044 nM
Inhibition of cysteinyl leukotriene receptor 1 (unknown origin) expressed in HEK293 cell membranes after 45 mins by scintillation spectrometry Homo sapiens 4.4 nM
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 3.81 %
Inhibition of recombinant human GALNS expressed in Pichia pastoris at 10 uM using 4-methylumbelliferyl-beta-D-galactopyranoside-6-sulfate as substrate measured after 18 hrs by fluorescence assay relative to control Homo sapiens 40.0 %
Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli BLR(DE3) assessed as reduction in NADPH level using L-serine, THF and NADP+ at 6.5 or 26.5 uM incubated for 5 mins by SHMT2-MTHFD coupled reaction based fluorescence assay relative to control Homo sapiens 65.5 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 34.72 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.2 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.85 %
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 0.74 % 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 0.3 % 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 0.12 % 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 0.3 % 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 0.74 % 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 0.12 %

Cross References

Resources Reference
ChEBI 94810
ChEMBL CHEMBL21333
DrugBank DB01411
DrugCentral 2237
FDA SRS TB8Z891092
Guide to Pharmacology 3634
PDB KNT
PubChem 4887
SureChEMBL SCHEMBL18058592
ZINC ZINC000001542146
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