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).
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2D Structure
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Physico-chemical Properties
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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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Canonical SMILES NCCON=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
Bioactivity Comments
Fluvoxamine has high affinity for the σ1 receptor and appears to act as a receptor agonist [1,3].
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
SERT Primary target of this compound Hs Inhibitor Inhibition 8.7 pKd - 9
pKd 8.7 (Kd 2.2x10-9 M) [9]
SERT Rn Inhibitor Inhibition 8.2 pKi - 4
pKi 8.2 (Ki 6.5x10-9 M) [4]
Description: Inhibition of [3]5-HT uptake into rat astrocyte cultures.
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
sigma non-opioid intracellular receptor 1 Hs None Binding 7.4 pKi - 8,11
pKi 7.4 (Ki 3.6x10-8 M) [8,11]
Description: Binding affinity.