LAROPIPRANT

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Synonyms
Status
Molecule Category UNKNOWN
UNII G7N11T8O78
EPA CompTox DTXSID60205756

Structure

InChI Key NXFFJDQHYLNEJK-CYBMUJFWSA-N
Smiles CS(=O)(=O)c1cc(F)cc2c3c(n(Cc4ccc(Cl)cc4)c12)[C@@H](CC(=O)O)CC3
InChI
InChI=1S/C21H19ClFNO4S/c1-29(27,28)18-10-15(23)9-17-16-7-4-13(8-19(25)26)20(16)24(21(17)18)11-12-2-5-14(22)6-3-12/h2-3,5-6,9-10,13H,4,7-8,11H2,1H3,(H,25,26)/t13-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H19ClFNO4S
Molecular Weight 435.9
AlogP 4.39
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 76.37
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Prostanoid DP receptor antagonist ANTAGONIST PubMed Other
Protein: Prostanoid DP receptor
Description: Prostaglandin D2 receptor
Organism : Homo sapiens
Q13258 ENSG00000168229
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Prostanoid receptor
- 0-4 0 1 -
Assay Description Organism Bioactivity Reference
Binding affinity to human DP receptor expressed in HEK293 cells Homo sapiens 0.57 nM Binding affinity to human DP receptor expressed in HEK293 cells Homo sapiens 0.03 nM
Binding affinity to human TP receptor expressed in HEK293 cells Homo sapiens 2.95 nM Binding affinity to human TP receptor expressed in HEK293 cells Homo sapiens 10.9 nM
Binding affinity to human EP2 receptor expressed in HEK293 cells Homo sapiens 136.0 nM
Binding affinity to human EP3 receptor expressed in HEK293 cells Homo sapiens 892.0 nM
Activity at human DP receptor in washed platelets assessed as inhibition of PGD2-induced cAMP accumulation Homo sapiens 0.09 nM
Activity at human DP receptor in platelet rich plasma assessed as inhibition of PGD2-induced cAMP accumulation Homo sapiens 4.0 nM
Activity at human TP receptor in platelet rich plasma assessed as inhibition U44619-induced platelet aggregation Homo sapiens 770.0 nM
Activity at CRTH2 receptor Homo sapiens 745.0 nM
Inhibition of PGD2-induced nasal airway resistance in sheep allergic rhinitis model at 0.03 mg/kg, iv Ovis aries 26.0 %
Inhibition of PGD2-induced nasal airway resistance in sheep allergic rhinitis model at 0.1 mg/kg, iv Ovis aries 99.0 %
Activity at sheep DP receptor by PRP assay Ovis aries 1.4 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 10.37 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 21.44 %
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 -0.02 %

Cross References

Resources Reference
ChEBI 135942
ChEMBL CHEMBL426559
DrugBank DB11629
DrugCentral 4326
FDA SRS G7N11T8O78
Guide to Pharmacology 3356
PharmGKB PA166129564
PubChem 9867642
SureChEMBL SCHEMBL991107
ZINC ZINC000003961849
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