LIXIVAPTAN

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Synonyms
Status
Molecule Category UNKNOWN
UNII 8F5X4B082E
EPA CompTox DTXSID00168472

Structure

InChI Key PPHTXRNHTVLQED-UHFFFAOYSA-N
Smiles Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1
InChI
InChI=1S/C27H21ClFN3O2/c1-17-8-9-19(29)13-23(17)26(33)30-20-10-11-22(24(28)14-20)27(34)32-16-21-6-4-12-31(21)15-18-5-2-3-7-25(18)32/h2-14H,15-16H2,1H3,(H,30,33)

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H21ClFN3O2
Molecular Weight 473.94
AlogP 6.05
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 54.34
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 34.0

Bioactivity

Mechanism of Action Action Reference
Vasopressin V2 receptor antagonist ANTAGONIST PubMed PubMed Wikipedia
Protein: Vasopressin V2 receptor
Description: Vasopressin V2 receptor
Organism : Homo sapiens
P30518 ENSG00000126895
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Vasopressin and oxytocin receptor
- 1-91 - 2-90 -
Assay Description Organism Bioactivity Reference
In vitro inhibition of [3H]- AVP binding to V1a receptor from human platelet membrane None 230.0 nM
Displacement of (Phe-3,4,5 [3H]-) AVP from isolated rat hepatic V1a receptor Rattus norvegicus 82.0 nM
In vitro inhibition of [3H]AVP binding to human V2 receptor from murine fibroblast cell line (LV2) None 1.2 nM
Displacement of P[3H]-AVP from isolated rat kidney medullary V2 receptor Rattus norvegicus 0.5 nM
Inhibition of 1 nM AVP-induced cAMP accumulation in cells expressing human vasopressin V2 receptor None 23.0 nM
Inhibition of [3H]AVP binding to recombinant human vasopressin V2 receptor None 2.3 nM
Binding affinity towards human V1a receptors None 150.0 nM
In vitro binding affinity to human V1a receptor Homo sapiens 230.0 nM
Inhibition of [3H]Arg-vasopressin binding to recombinant human vasopressin V1a receptor Homo sapiens 150.0 nM
Inhibition of [3H]AVP binding to recombinant human vasopressin V1a receptor Homo sapiens 44.0 nM
In vitro binding affinity for rat V1a receptor Rattus norvegicus 340.0 nM
Inhibition of [3H]AVP binding to Dawley rat hepatic vasopressin V1a receptor. None 410.0 nM
In vitro binding affinity to human V2 receptor Homo sapiens 1.2 nM
Displacement of [3H]AVP from human vasopressin V2-receptor expressed in murine fibroblast cell (LV2) membranes Homo sapiens 1.2 nM
Inhibition of [3H]Arg-vasopressin binding to recombinant human vasopressin V2 receptor Homo sapiens 5.0 nM
Inhibitory activity of the human V2 receptor was assessed by the accumulation of cAMP in transfected HEK293 cells. None 5.0 nM Inhibitory activity of the human V2 receptor was assessed by the accumulation of cAMP in transfected HEK293 cells. None 91.0 nM
Inhibition of AVP mediated activation of human vasopressin V2 receptor expressed in HEK293 cells Homo sapiens 90.0 nM
Binding affinity to rat V2 receptor Rattus norvegicus 2.3 nM
Inhibition of [3H]AVP binding to Dawley rat kidney medullary vasopressin V2 receptor. None 2.3 nM
Displacement of [3H]AVP from vasopressin receptor (V1a) from human platelet membranes. Homo sapiens 230.0 nM
Displacement of (Phe-3,4,5-H) Vasopressin from V1a receptor from rat liver membranes. Rattus norvegicus 340.0 nM
Displacement of [3H]AVP from human V2 receptor expressed in murine fibroblast cell line (LV2) membranes Homo sapiens 1.2 nM
Displacement of [3H]AVP from vasopressin V2 receptor of rat kidney medulla. Rattus norvegicus 2.3 nM
Inhibitory concentration against [3H]AVP binding to human vasopressin V1a receptor Homo sapiens 180.0 nM
Inhibition of [3H]-AVP binding to human V2 receptor Homo sapiens 1.0 nM
Displacement of [3H]AVP from human vasopressin V2 receptor expressed in mouse LV2 cells Homo sapiens 1.2 nM
Displacement of [3H]manning ligand from human vasopressin V1a receptor expressed in CHO cells Homo sapiens 124.0 nM
Displacement of [3H]oxytocin from human oxytocin receptor expressed in CHO cells Homo sapiens 519.0 nM
Displacement of [3H]Arg-vasopressin from human recombinant vasopressin V1a receptor expressed in HEK293 cells Homo sapiens 150.0 nM
Displacement of [3H]Arg-vasopressin from human recombinant vasopressin V2 receptor expressed in HEK293 cells Homo sapiens 5.0 nM
Antagonist activity at human vasopressin V2 receptor expressed in HEK293 cells assessed as inhibition of Arg-vasopressin-induced cAMP levels Homo sapiens 91.0 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 -5.49 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 29.92 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.91 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -6.12 %
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 0.09 % 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 1.31 % 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 1.31 % 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 -0.12 %

Cross References

Resources Reference
ChEMBL CHEMBL49429
DrugBank DB06666
FDA SRS 8F5X4B082E
Guide to Pharmacology 2238
PubChem 172997
SureChEMBL SCHEMBL1649340
ZINC ZINC000000600399
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