NEFAZODONE

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Synonyms
Status
Molecule Category Free-form
ATC N06AX06
UNII 59H4FCV1TF
EPA CompTox DTXSID2023357

Structure

InChI Key VRBKIVRKKCLPHA-UHFFFAOYSA-N
Smiles CCc1nn(CCCN2CCN(c3cccc(Cl)c3)CC2)c(=O)n1CCOc1ccccc1
InChI
InChI=1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H32ClN5O2
Molecular Weight 470.02
AlogP 3.55
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 10.0
Polar Surface Area 55.53
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 33.0
Assay Description Organism Bioactivity Reference
Equilibrium dissociation constant (KD) for Competitive binding between [3H]WIN-35428 and the compound at human transporter-hDAT None 360.0 nM
Equilibrium dissociation constant (KD) for Competitive binding between [3H]- nisoxatine and the compound at human Norepinephrine transporter None 360.0 nM
Inhibition of [3H]- NE reuptake into rat hippocampal synaptosomes None 570.0 nM
Inhibition of [3H]5-HT reuptake into rat frontal cortex synaptosomes None 137.0 nM
Equilibrium dissociation constant (KD) for Competitive binding between [3H]- imipramine and the compound at human transporter-hSERT None 200.0 nM
Binding affinity to 5HT1A receptor None 158.49 nM
Binding affinity to SERT None 290.0 nM
Binding affinity to 5-HT2A None 5.8 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 12.0 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 61.4 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 61.5 %
Time dependent inhibition of CYP3A4 in human liver microsomes Homo sapiens 15.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 31.97 nM
Binding affinity to rat 5HT1A receptor Rattus norvegicus 52.0 nM
Binding affinity to rat 5HT2A receptor Rattus norvegicus 7.0 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 17.25 %
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 -0.01 % 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 -0.01 %

Cross References

Resources Reference
ChEBI 7494
ChEMBL CHEMBL623
DrugBank DB01149
DrugCentral 1890
FDA SRS 59H4FCV1TF
Human Metabolome Database HMDB0015280
Guide to Pharmacology 7247
KEGG C07256
PharmGKB PA450603
PubChem 4449
SureChEMBL SCHEMBL35089
ZINC ZINC000000538065
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