VENLAFAXINE

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Synonyms
Status
Molecule Category Free-form
ATC N06AX16
UNII GRZ5RCB1QG
EPA CompTox DTXSID6023737

Structure

InChI Key PNVNVHUZROJLTJ-UHFFFAOYSA-N
Smiles COc1ccc(C(CN(C)C)C2(O)CCCCC2)cc1
InChI
InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H27NO2
Molecular Weight 277.41
AlogP 3.04
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 32.7
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 20.0
Assay Description Organism Bioactivity Reference
Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain None 90.0 nM Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain None 109.0 nM Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain None 140.0 nM
Binding affinity against norepinephrine transporter (NET) by displacement of [3H]nisoxetine in male wistar rats None 719.0 nM
Inhibition of uptake of tritiated norepinephrine (NE) into rat brain synaptosomes None 640.0 nM Inhibition of uptake of tritiated norepinephrine (NE) into rat brain synaptosomes None 760.0 nM
Inhibition of uptake of tritiated serotonin (5-HT) into rat brain synaptosomes None 210.0 nM Inhibition of uptake of tritiated serotonin (5-HT) into rat brain synaptosomes None 100.0 nM Inhibition of uptake of tritiated serotonin (5-HT) into rat brain synaptosomes None 190.0 nM
Inhibition of [3H]- DA reuptake into rat striatal synaptosomes None 360.0 nM
Inhibition of [3H]- NE reuptake into rat hippocampal synaptosomes None 138.0 nM
Inhibition of [3H]5-HT reuptake into rat frontal cortex synaptosomes None 37.0 nM
Equilibrium dissociation constant (KD) for Competitive binding between [3H]- imipramine and the compound at human transporter-hSERT None 8.9 nM
Binding affinity to the serotonin transporter (SERT) measured by displacement of [3H]paroxetine in male wistar rats None 52.0 nM
Displacement of [3H]nisoxetine from human norepinephrine transporter expressed in MDCK-Net6 cells Homo sapiens 385.0 nM
Inhibition of norepinephrine uptake at human norepinephrine transporter expressed in MDCK-Net6 cells Homo sapiens 535.0 nM
Inhibition of 5HT uptake at human SERT expressed in human JAR cells Homo sapiens 31.0 nM
Inhibition of norepinephrine uptake at rat brain norepinephrine transporter Rattus norvegicus 640.0 nM
Inhibition of 5HT uptake at rat brain SERT Rattus norvegicus 210.0 nM
Inhibition of human recombinant CYP2D6 at 5 uM assessed as blockade of O-demethylation of dextromethorphan in to dextrophan by nanoscale automated in-capillary assay Homo sapiens 0.0 %
Inhibition of [3H]5HT reuptake at rat brain frontal cortex serotonin transporter Rattus norvegicus 350.0 nM
Inhibition of human NET transfected in MDCK-Net6 cells Homo sapiens 535.0 nM
Inhibition of human SERT expressed in human JAR cells Homo sapiens 27.0 nM
Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells Homo sapiens 35.0 nM
Inhibition of norepinephrine reuptake at human NET expressed in MDCK cells Homo sapiens 581.0 nM
Analgesic activity in mouse assessed as reduction of acetic acid-induced writhing at 30 mg/kg, po Mus musculus 70.2 %
Anxiolytic activity in mouse assessed as inhibition of marble buried at 30 mg/kg, ip by marble burying test Mus musculus 82.3 %
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 7.18 nM DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 3.814 nM
Inhibition of NET None 149.0 nM
Inhibition of SERT None 20.0 nM
Displacement of [3H]-nisoxetine from Sprague-Dawley rat brain NET after 1 hr Rattus norvegicus 500.0 nM
Displacement of [3H]-citalopram from Sprague-Dawley rat brain SERT after 1 hr Rattus norvegicus 25.0 nM
Displacement of [3H]WIN35428 from human DAT transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 890.0 nM
Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 680.0 nM Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 553.0 nM
Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 20.0 nM Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 11.0 nM
Inhibition of [3H]5-HT uptake at human SERT expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay Homo sapiens 113.0 nM Inhibition of [3H]5-HT uptake at human SERT expressed in HEK293 cells preincubated for 10 mins prior to substrate addition measured after 4 mins by FLIPR assay Homo sapiens 323.59 nM
Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells at 0.1 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 56.0 %
Inhibition of norepinephrine reuptake at human NET expressed in HEK293 cells at 0.1 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 9.0 %
Inhibition of DA reuptake at human DAT expressed in HEK293 cells at 0.1 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 6.0 %
Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 36.1 nM
Inhibition of norepinephrine reuptake at human NET expressed in HEK293 cells at 1 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 37.0 %
Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells at 1 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 86.0 %
Inhibition of DA reuptake at human DAT expressed in HEK293 cells at 10 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 56.0 %
Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells at 10 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 92.0 %
Inhibition of norepinephrine reuptake at human NET expressed in HEK293 cells at 10 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 81.0 %
Inhibition of DA reuptake at human DAT expressed in HEK293 cells at 1 uM after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 16.0 %
Antidepressant activity in rat assessed as reduction in immobility time at 30 mg/kg, po by forced swimming test relative to control Rattus norvegicus 14.0 %
Binding affinity to human SERT expressed in HEK293 cells after 60 mins in presence of [3H]imipramine by liquid scintillation counting Homo sapiens 39.0 nM
Binding affinity to human NET expressed in HEK293 cells after 60 mins in presence of [3H]imipramine by liquid scintillation counting Homo sapiens 210.0 nM
Inhibition of human SERT expressed in HEK293 cells assessed as decrease in [3H]-serotonin reuptake after 10 mins by scintillation counting method Homo sapiens 20.0 nM
Inhibition of human NET expressed in MDCK cells assessed as decrease in [3H]-noradrenaline reuptake after 10 mins by scintillation counting method Homo sapiens 149.0 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 0.44 %
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 0.11 % 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 0.11 %

Related Entries

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Cross References

Resources Reference
ChEBI 9943
ChEMBL CHEMBL637
DrugBank DB00285
DrugCentral 2813
FDA SRS GRZ5RCB1QG
Human Metabolome Database HMDB0005016
Guide to Pharmacology 7321
KEGG C07187
PharmGKB PA451866
PubChem 5656
SureChEMBL SCHEMBL35154
CONTENTS