ALOSETRON

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Synonyms
Status
Molecule Category Free-form
ATC A03AE01
UNII 13Z9HTH115
EPA CompTox DTXSID6044278

Structure

InChI Key JSWZEAMFRNKZNL-UHFFFAOYSA-N
Smiles Cc1[nH]cnc1CN1CCc2c(c3ccccc3n2C)C1=O
InChI
InChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H18N4O
Molecular Weight 294.36
AlogP 2.41
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 53.92
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 22.0
Assay Description Organism Bioactivity Reference
Binding affinity to human HT3A receptor Homo sapiens 0.5 nM
Inhibition of human CYP3A4 Homo sapiens 600.0 nM
Binding affinity to human 5HT3A receptor Homo sapiens 0.5 nM
Inhibition of human CYP3A4 Homo sapiens 600.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 100.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 64.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT3 radioligand binding (ligand: [3H] GR-65630) None 1.164 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT3 radioligand binding (ligand: [3H] GR-65630) None 0.262 nM
DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 604.7 nM
Displacement of [9-methyl-3H]BRL-43694 from human 5-HT3A receptor after overnight incubation by scintillation proximity assay Homo sapiens 0.5 nM
Inhibition of CYP3A4 (unknown origin) Homo sapiens 600.0 nM
Inhibition of 5-HT induced-bradycardia in ICR mouse von Bezold-Jarisch reflex model at 1 mg/kg, po after 60 mins relative to control Mus musculus 95.0 %
Radioligand Binding Assay: The relative affinity of the various compounds for the human 5-HT3 receptor was measured in a radioligand binding assay, using a scintillation proximity assay (SPA) format. Test compounds were dissolved to 10 mM in 100% DMSO, then serially diluted at 10x assay concentrations in 100% DMSO in 96-well polypropylene plates and further diluted to 4x assay concentrations with the assay buffer. Samples were incubated in 50 mM Tris-HCl, pH 7.5, 3 mM MgCl2, 1 mM EDTA and 10% DMSO with 10 nM [9-methyl-3H]BRL-43694 (Perkin Elmer), 3 ug of human 5-HT3 receptor membranes (Perkin Elmer) and 0.5 mg/mL SPA beads (WGA PVT, Amersham Biosciences) in a final volume of 0.2 mL. Binding reactions were set up in wells of PicoPlates-96 (Perkin Elmer) by adding consecutively 50 uL of each competing compound or buffer, SPA beads, the radioligand and 5-HT3 receptor membranes. After an overnight incubation at room temperature on a Nutator mixer, plates were centrifuged for 15 min at 1,500 rpm. Homo sapiens 0.5 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 7.0 %
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 0.03 % 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 0.03 %

Cross References

Resources Reference
ChEBI 253342
ChEMBL CHEMBL1110
DrugBank DB00969
DrugCentral 129
FDA SRS 13Z9HTH115
Human Metabolome Database HMDB0015104
Guide to Pharmacology 2296
PDB S7Y
PharmGKB PA164745502
PubChem 2099
SureChEMBL SCHEMBL631
ZINC ZINC000013537284
CONTENTS