fluvoxamine   Click here for help

GtoPdb Ligand ID: 7189

Synonyms: Luvox® | U-23000
Approved drug PDB Ligand Immunopharmacology Ligand
fluvoxamine is an approved drug (FDA (1994))
Compound class: Synthetic organic
Comment: Fluvoxamine is an antidepressant belonging to the selective serotonin reuptake inhibitor (SSRI) drug group.
Marketed formulations may contain fluvoxamine maleate (PubChem CID 9560989).

SARS-CoV-2 and COVID-19: Evidence that is emerging from randomised, placebo-controlled clinical trials [6] suggests that fluvoxamine may offer potential as a therapuetic for non-hospitalised COVID-19 patients. Multiple fluvoxamine mechanisms of action may be at play [10], and much remains to clarified about the patients who would benefit most, efficacy in infections with different SARS-CoV-2 variants, and whether fluvoxamine's effect occurs in addition to the benefit demonstrated by other therapies.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: fluvoxamine

fluvoxamine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 56.84
Molecular weight 318.16
XLogP 3.24
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCCO/N=C(/c1ccc(cc1)C(F)(F)F)\CCCCOC
Isomeric SMILES NCCO/N=C(/c1ccc(cc1)C(F)(F)F)\CCCCOC
InChI InChI=1S/C15H21F3N2O2/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18/h5-8H,2-4,9-11,19H2,1H3/b20-14+
InChI Key CJOFXWAVKWHTFT-XSFVSMFZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to treat major depressive episodes and obsessive compulsive disorder (OCD).

SARS-CoV-2 and COVID-19: The potential of fluvoxamine has been evaluated in symptomatic COVID-19 outpatients, with preliminary signs of benefit [5]. Fluvoxamine is propsed to modulate the effects of peripheral serotonin on systemic inflammation [12] in COVID-19 [2]. It may also have a beneficial effect via regulation of platelet-derived serotonin's role in recruiting innate immune cells (that express 5-HT receptors) to sites of inflammation [8].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
SSRIs increase serotonin levels at post-synaptic sites by inhibiting the pre-synaptic transporter, SERT (SLC6A4), normally involved in serotonin re-uptake. This enhances serotonergic neurotransmission with the clinical outcomes being improved mood and decreased anxiety. See the DrugBank link for further details.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04342663 A Double-blind, Placebo-controlled Clinical Trial of Fluvoxamine for Symptomatic Individuals With COVID-19 Infection Phase 2 Interventional Washington University School of Medicine The preliminary signs of efficacy observed in this study (reduction in chance of clinical deterioration over 15 days in treatment arm) would need to be followed up in larger scale RCTs with a longer follow-up timescale. 5
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com