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.
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fluvoxamine

fluvoxamine is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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/)

✖
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/)
References
1. Cobos EJ, Entrena JM, Nieto FR, Cendán CM, Del Pozo E. (2008)
Pharmacology and therapeutic potential of sigma(1) receptor ligands.
Curr Neuropharmacol, 6 (4): 344-66. [PMID:19587856]
2. Costa LHA, Santos BM, Branco LGS. (2020)
Can selective serotonin reuptake inhibitors have a neuroprotective effect during COVID-19?.
Eur J Pharmacol, 889: 173629. [PMID:33022271]
3. Hashimoto K. (2015)
Activation of sigma-1 receptor chaperone in the treatment of neuropsychiatric diseases and its clinical implication.
J Pharmacol Sci, 127 (1): 6-9. [PMID:25704012]
4. Inazu M, Takeda H, Ikoshi H, Sugisawa M, Uchida Y, Matsumiya T. (2001)
Pharmacological characterization and visualization of the glial serotonin transporter.
Neurochem Int, 39 (1): 39-49. [PMID:11311448]
5. Lenze EJ, Mattar C, Zorumski CF, Stevens A, Schweiger J, Nicol GE, Miller JP, Yang L, Yingling M, Avidan MS et al.. (2020)
Fluvoxamine vs Placebo and Clinical Deterioration in Outpatients With Symptomatic COVID-19: A Randomized Clinical Trial.
JAMA, 324 (22): 2292-2300. [PMID:33180097]
6. Reis G, dos Santos Moreira-Silva EA, Silva DCM, Thabane L, Milagres AC, Ferreira TS, dos Santos CVQ, de Souza Campos VH, Nogueira AMR, de Almeida APFG et al.. (2021)
Effect of early treatment with fluvoxamine on risk of emergency care and hospitalisation among patients with COVID-19: the TOGETHER randomised, platform clinical trial.
The Lancet Global Health, Epub ahead of print. DOI: 10.1016/S2214-109X(21)00448-4
7. Rosen DA, Seki SM, Fernández-Castañeda A, Beiter RM, Eccles JD, Woodfolk JA, Gaultier A. (2019)
Modulation of the sigma-1 receptor-IRE1 pathway is beneficial in preclinical models of inflammation and sepsis.
Sci Transl Med, 11 (478). [PMID:30728287]
8. Schoenichen C, Bode C, Duerschmied D. (2019)
Role of platelet serotonin in innate immune cell recruitment.
Front Biosci (Landmark Ed), 24: 514-526. [PMID:30468670]
9. Stahl SM. (2008)
The sigma enigma: can sigma receptors provide a novel target for disorders of mood and cognition?.
J Clin Psychiatry, 69 (11): 1673-4. [PMID:19200426]
10. Sukhatme VP, Reiersen AM, Vayttaden SJ, Sukhatme VV. (2021)
Fluvoxamine: A Review of Its Mechanism of Action and Its Role in COVID-19.
Front Pharmacol, 12: 652688. [PMID:33959018]
11. Tatsumi M, Groshan K, Blakely RD, Richelson E. (1997)
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.
Eur J Pharmacol, 340 (2-3): 249-58. [PMID:9537821]
12. Wu H, Denna TH, Storkersen JN, Gerriets VA. (2019)
Beyond a neurotransmitter: The role of serotonin in inflammation and immunity.
Pharmacol Res, 140: 100-114. [PMID:29953943]
13. Yu LF, Zhang HK, Gunosewoyo H, Kozikowski AP. (2012)
From α4β2 Nicotinic Ligands to the Discovery of σ1 Receptor Ligands: Pharmacophore Analysis and Rational Design.
ACS Med Chem Lett, 3 (12): 1054-1058. [PMID:23641311]