FLUOXETINE HYDROCHLORIDE

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Synonyms
Status
Molecule Category Salt-form
UNII I9W7N6B1KJ
EPA CompTox DTXSID7020635

Structure

InChI Key GIYXAJPCNFJEHY-UHFFFAOYSA-N
Smiles CNCCC(Oc1ccc(C(F)(F)F)cc1)c1ccccc1.Cl
InChI
InChI=1S/C17H18F3NO.ClH/c1-21-12-11-16(13-5-3-2-4-6-13)22-15-9-7-14(8-10-15)17(18,19)20;/h2-10,16,21H,11-12H2,1H3;1H

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H19ClF3NO
Molecular Weight 345.79
AlogP 4.44
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 21.26
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Serotonin transporter inhibitor INHIBITOR PubMed PubMed DailyMed
Protein: Serotonin transporter
Description: Sodium-dependent serotonin transporter
Organism : Homo sapiens
P31645 ENSG00000108576
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 72 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 150 - 1 44
Assay Description Organism Bioactivity Reference
Displacement of [3H]citalopram from serotonin transporter in Sprague-Dawley rat brain after 1 hr by liquid scintillation counting Rattus norvegicus 2.0 nM
Displacement of [3H]WIN 35428 from dopamine transporter in Sprague-Dawley rat brain after 1 hr by liquid scintillation counting Rattus norvegicus 784.0 nM
Displacement of [3H]nisoxetine from norepinephrine transporter in Sprague-Dawley rat frontal cortex after 1 hr by liquid scintillation counting Rattus norvegicus 473.0 nM
Selectivity ratio of Ki for dopamine transporter in Sprague-Dawley rat brain to Ki for serotonin transporter in Sprague-Dawley rat brain Rattus norvegicus 392.0 nM
Displacement of [3H]Citalopram from human SERT by liquid scintillation counting Homo sapiens 1.1 nM
Binding affinity to human 5HT2C receptor by radioligand displacement assay Homo sapiens 72.0 nM
Inhibition of human SERT expressed in HEK293 cells assessed as inhibition of serotonin reuptake after 30 mins by fluorescence assay Homo sapiens 150.0 nM
Inhibition of human DAT expressed in HEK293 cells assessed as inhibition of dopamine reuptake at 0.1 uM after 15 mins by fluorescence assay Homo sapiens 5.8 %
Inhibition of human NET expressed in HEK293 cells assessed as inhibition of noradrenaline reuptake at 0.1 uM after 15 mins by fluorescence assay Homo sapiens 4.7 %
Inhibition of human SERT expressed in HEK293 cells assessed as inhibition of serotonin reuptake at 0.1 uM after 15 mins by fluorescence assay Homo sapiens 44.0 %
Antidepressant activity in Mus musculus (mouse) assessed as decrease in immobility at 15 mg/kg, ip measured after 30 min by despair swim test Mus musculus 58.59 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 15.46 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.53 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 3.44 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 11.84 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 17.55 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.79 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -8.4 %
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 8.64 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.847 %
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 1.83 % 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 1.83 %
Inhibition of LPS-induced nitric oxide production in human BV-2 cells at 10 uM measured after 24 hrs by Griess reagent assay relative to control Homo sapiens 31.2 %

Cross References

Resources Reference
ChEBI 145458
ChEMBL CHEMBL1201082
FDA SRS I9W7N6B1KJ
SureChEMBL SCHEMBL33384
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