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

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 CDK toolkit. 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
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.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1994))
IUPAC Name Click here for help
2-[(E)-[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine
International Nonproprietary Names Click here for help
INN number INN
3879 fluvoxamine
Synonyms Click here for help
Luvox® | U-23000
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9679783
Reactome Reaction Reactome logo R-HSA-9679780
Other databases
CAS Registry No. 54739-18-3
ChEBI CHEBI:5138
ChEMBL Ligand CHEMBL814
DrugBank Ligand DB00176
DrugCentral Ligand 1230
GtoPdb PubChem SID 178103764
PubChem CID 5324346
RCSB PDB Ligand FVX
Search Google for chemical match using the InChIKey CJOFXWAVKWHTFT-XSFVSMFZSA-N
Search Google for chemicals with the same backbone CJOFXWAVKWHTFT
Search PubMed clinical trials fluvoxamine
Search PubMed titles fluvoxamine
Search PubMed titles/abstracts fluvoxamine
UniChem Compound Search for chemical match using the InChIKey CJOFXWAVKWHTFT-XSFVSMFZSA-N
UniChem Connectivity Search for chemical match using the InChIKey CJOFXWAVKWHTFT-XSFVSMFZSA-N
Wikipedia Fluvoxamine