RUPATADINE

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Synonyms
Status
Molecule Category UNKNOWN
ATC R06AX28
UNII 2AE8M83G3E
EPA CompTox DTXSID00166534

Structure

InChI Key WUZYKBABMWJHDL-UHFFFAOYSA-N
Smiles Cc1cncc(CN2CCC(=C3c4ccc(Cl)cc4CCc4cccnc43)CC2)c1
InChI
InChI=1S/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H26ClN3
Molecular Weight 415.97
AlogP 5.63
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 2.0
Polar Surface Area 29.02
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 30.0

Bioactivity

Mechanism of Action Action Reference
Histamine H1 receptor antagonist ANTAGONIST PubMed PubMed
Protein: Platelet activating factor receptor
Description: Platelet-activating factor receptor
Organism : Homo sapiens
P25105 ENSG00000169403
Protein: Histamine H1 receptor
Description: Histamine H1 receptor
Organism : Homo sapiens
P35367 ENSG00000196639
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) PAF receptor
- 3700 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 4 - 4 -
Assay Description Organism Bioactivity Reference
Tested for concentration required to inhibit H1 histamine -induced guinea pig ileum contraction Cavia porcellus 3.9 nM
Tested at 10 (mg/kg) intravenous dose for percent inhibition of the arterial blood pressure in normotensive rats caused by histamine Rattus norvegicus 89.0 %
Inhibitory concentration against histamine H1 receptor Homo sapiens 3.9 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 72.14 %
Displacement of [3H]mepyramine from N-terminal HA-tagged H1R (unknown origin) expressed in HEK293T cells measured after 4 hrs by microbeta scintillation counting method Homo sapiens 3.981 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.59 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.831 %
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 8.73 % 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 0.75 % 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 8.73 % 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 0.75 %

Related Entries

Cross References

Resources Reference
ChEBI 135673
ChEMBL CHEMBL91397
DrugBank DB11614
DrugCentral 2413
FDA SRS 2AE8M83G3E
Human Metabolome Database HMDB0240234
Guide to Pharmacology 10103
PharmGKB PA165107052
PubChem 133017
SureChEMBL SCHEMBL27703
ZINC ZINC000000598829
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