DULOXETINE

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Synonyms
Status
Molecule Category Free-form
ATC N06AX21
UNII O5TNM5N07U
EPA CompTox DTXSID6048385

Structure

InChI Key ZEUITGRIYCTCEM-KRWDZBQOSA-N
Smiles CNCC[C@H](Oc1cccc2ccccc12)c1cccs1
InChI
InChI=1S/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H19NOS
Molecular Weight 297.42
AlogP 4.63
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 21.26
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Ability to inhibit [3H]WIN-35428 binding to cloned human dopamine (DA) transporter Homo sapiens 240.0 nM
Ability to inhibit the reuptake of dopamine at human dopamine transporter None 240.0 nM
Ability to inhibit the reuptake of NE at human norepinephrine transporter None 7.5 nM
Ability to inhibit [3H]nisoxetine binding to cloned human norepinephrine (NE) transporter Homo sapiens 7.45 nM
Inhibition of dopamine uptake into rat synaptosomes Rattus norvegicus 370.0 nM
Inhibition of norepinephrine uptake into rat synaptosomes Rattus norvegicus 16.0 nM
Inhibition of serotonin uptake into rat synaptosomes Rattus norvegicus 4.6 nM
Ability to inhibit [3H]paroxetine binding to cloned human serotonin (5-HT) transporter Homo sapiens 0.79 nM
Ability to inhibit the reuptake of 5-HT at human serotonin transporter None 0.8 nM
Binding affinity for Dopamine transporter None 240.0 nM
Binding affinity for Norepinephrine transporter None 7.5 nM
Binding affinity for 5-hydroxytryptamine transporter None 0.8 nM
Inhibition constant against dopamine transporter Homo sapiens 370.0 nM
Inhibition constant against serotonin transporter Homo sapiens 4.6 nM
Inhibition constant against norepinephrine transporter Homo sapiens 16.0 nM
Inhibition of [3H]5-HT reuptake at 5HT transporter in HEK293 cells Homo sapiens 6.0 nM
Inhibition of [3H]NA reuptake at NA transporter in HEK293 cells Homo sapiens 19.0 nM
Inhibition of [3H]DA reuptake at DA transporter in HEK293 cells Homo sapiens 870.0 nM
Inhibition of [3H]5-HT uptake at 5HT transporter expressed in HEK293 cells Homo sapiens 6.0 nM
Inhibition of [3H]NA uptake at NA transporter expressed in HEK293 cells Homo sapiens 19.0 nM
Inhibition of DA transporter expressed in HEK293 cells Homo sapiens 870.0 nM
Inhibition of [3H]5-HT from human SERT expressed in HEK293 cells Homo sapiens 6.0 nM
Inhibition of [3H]NA from human NET expressed in HEK293 cells Homo sapiens 19.0 nM
Inhibition of [3H]DA from human DAT expressed in HEK293 cells Homo sapiens 870.0 nM
Inhibition of human NET Homo sapiens 8.9 nM
Inhibition of human SERT Homo sapiens 6.6 nM
Inhibition of human DAT Homo sapiens 660.0 nM
Inhibition of [3H]citalopram uptake at human 5HTT expressed in HEK293 cells Homo sapiens 5.0 nM
Inhibition of [3H]nisoxetine reuptake at human NET expressed in HEK293 cells Homo sapiens 45.0 nM
Inhibition of [3H]dopamine reuptake at human DAT expressed in HEK293 cells Homo sapiens 435.0 nM
Displacement of Levo[ring-2,5,6-3H]norepinephrine from human cloned NET expressed in HEK293 cells by microplate scintillation counter Homo sapiens 8.9 nM
Displacement of [alpha,beta-3H(N)]-5-hydroxytryptamine from human cloned SERT expressed in HEK293 cells by microplate scintillation counter Homo sapiens 6.6 nM
Displacement of 3,4-[ring-2,5,6-3H]dihydroxyphenylethylamine from human cloned DAT expressed in HEK293 cells by microplate scintillation counter Homo sapiens 660.0 nM
Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells Homo sapiens 4.0 nM
Inhibition of serotonin uptake at human SERT expressed in human JAR cells Homo sapiens 3.0 nM
Inhibition of norepinephrine uptake at human NET expressed in MDCK cells Homo sapiens 4.0 nM
Inhibition of serotonin uptake at human SERT expressed in JAR cells Homo sapiens 3.0 nM
Displacement of [125I]RTI55 from DAT in Sprague-dawley rat striatum by liquid scintillation spectrophotometry Rattus norvegicus 370.0 nM
Displacement of [3H]nisoxetine from Sprague-dawley rat NET by liquid scintillation spectrophotometry Rattus norvegicus 16.0 nM
Displacement of [3H]citalopram from SERT in Sprague-dawley rat frontal cortex by liquid scintillation spectrophotometry Rattus norvegicus 4.6 nM
Inhibition of [3H]NA uptake at human NET expressed in HEK293 cells Homo sapiens 5.0 nM
Inhibition of [3H]5-HT uptake at human 5HTT expressed in HEK293 cells Homo sapiens 4.0 nM
Inhibition of [3H]DA uptake at human DAT expressed in HEK293 cells Homo sapiens 590.0 nM
Inhibition of SERT None 0.5012 nM
Inhibition of NET None 7.943 nM
Inhibition of DAT None 251.19 nM
Displacement of [3H]5HT from human 5HT transporter expressed in HEK293 cells by scintillation counting Homo sapiens 5.0 nM
Displacement of [3H]noradrenaline from human NET receptor expressed in HEK293 cells by scintillation counting Homo sapiens 45.0 nM
Displacement of [3H]dopamine from human DAT receptor expressed in HEK293 cells by scintillation counting Homo sapiens 435.0 nM
Inhibition of human NET transfected in MDCK-Net6 cells Homo sapiens 4.0 nM
Inhibition of human SERT expressed in human JAR cells Homo sapiens 3.0 nM
Displacement of [3H]citalopram from human SERT expressed in HEK293 cells by scintillation proximity assay Homo sapiens 5.0 nM
Displacement of [3H]nisoxetine from human NET expressed in HEK293 cells by scintillation proximity assay Homo sapiens 45.0 nM
Displacement of [3H]dopamine from human DAT expressed in HEK293 cells by scintillation proximity assay Homo sapiens 435.0 nM
Displacement of [3H]nisoxetine from rat NET in rat cerebral cortex Rattus norvegicus 3.0 nM
Inhibition of rat NET Rattus norvegicus 3.9 nM
Inhibition of human NET Homo sapiens 5.97 nM
Antinociceptive activity in rat assessed reduction formalin-induced hind paw acute pain at 10 mg/kg, ip Rattus norvegicus 49.0 %
Displacement of [3H]WIN35428 from human recombinant DAT transfected in HEK293 cell membrane Homo sapiens 316.23 nM
Inhibition of human recombinant SERT expressed in HEK293 cells assessed as inhibition of [3H]5HT reuptake Homo sapiens 0.3162 nM
Inhibition of human recombinant NET expressed in HEK293 cells assessed as inhibition of [3H]NE reuptake Homo sapiens 1.585 nM
Inhibition of [3H]5-HT reuptake at SERT in rat brain synaptosomes at 10 uM Rattus norvegicus 89.5 %
Inhibition of [3H]NE reuptake at NET in rat brain synaptosomes at 10 uM Rattus norvegicus 81.4 %
Displacement of [3H]-nisoxetine from Sprague-Dawley rat brain NET after 1 hr Rattus norvegicus 1.24 nM
Displacement of [3H]-citalopram from Sprague-Dawley rat brain SERT after 1 hr Rattus norvegicus 0.082 nM
Displacement of [3H]WIN35428 from human DAT transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 484.0 nM
Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 29.0 nM Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 6.7 nM
Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 2.3 nM Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after 3 hrs by Wallac counting analysis Homo sapiens 0.24 nM
Inhibition of human SERT expressed in HEK293 cells at incubated for 15 mins by neurotransmitter reuptake assay Homo sapiens 10.4 nM
Inhibition of human NET expressed in HEK293 cells at incubated for 15 mins by neurotransmitter reuptake assay Homo sapiens 515.0 nM
Inhibition of human DAT expressed in HEK293 cells at incubated for 15 mins by neurotransmitter reuptake assay Homo sapiens 977.0 nM
Inhibition of human recombinant CYP3A4 incubated for 5 mins by fluorescence assay Homo sapiens 440.0 nM
Inhibition of serotonin reuptake at human SERT expressed in HEK293 cells after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 10.4 nM
Inhibition of norepinephrine reuptake at human NET expressed in HEK293 cells after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 515.0 nM
Inhibition of DA reuptake at human DAT expressed in HEK293 cells after 15 mins by fluorescence neurotransmitter transporter assay Homo sapiens 977.0 nM
Inhibition of recombinant human CYP3A4 preincubated for 5 mins before fluorescent substrate addition by fluorescence assay Homo sapiens 440.0 nM
Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli BLR(DE3) assessed as reduction in NADPH level using L-serine, THF and NADP+ at 6.5 or 26.5 uM incubated for 5 mins by SHMT2-MTHFD coupled reaction based fluorescence assay relative to control Homo sapiens 83.8 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.22 %
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 6.99 % 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 6.99 %

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Slovakia
Slovenia

Cross References

Resources Reference
ChEBI 36795
ChEMBL CHEMBL1175
DrugBank DB00476
DrugCentral 972
FDA SRS O5TNM5N07U
Human Metabolome Database HMDB0014619
Guide to Pharmacology 202
PDB 29E
PharmGKB PA10066
PubChem 60835
SureChEMBL SCHEMBL8291
ZINC ZINC000001536779
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