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
References
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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. 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]
7. 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]
8. 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]
9. 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]
10. 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]
11. 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]