viloxazine   Click here for help

GtoPdb Ligand ID: 11502

Synonyms: Emovit® | ICI-58,834 | ICI-58834 | Qelbree®
Approved drug
viloxazine is an approved drug (FDA (2021))
Compound class: Synthetic organic
Comment: Viloxazine was originally described as a selective norepinephrine reuptake inhibitor (NRI), principally based on its ability to potentiate noradrenergic effects. It also modulates 5-HT (serotonin) activity, via antagonistic activity at 5-HT2B and agonistic activity at 5-HT2C receptors, and it increases extracellular 5-HT levels in the prefrontal cortex (PFC) [3]. Viloxazine's chemical structure is different from conventional tri- or tetra-cyclic antidepressants. The INN stipulates a racemic mixture of enantiomers. We show the structure without specified stereochemistry to represent the mixture. The hydrocholride salt (SPN-812) was progressed by Supernus Pharmaceuticals for attention deficit hyperactivity disorder (ADHD) in children and adults.
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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 5
Topological polar surface area 39.72
Molecular weight 237.14
XLogP 1.26
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOc1ccccc1OCC1CNCCO1
Isomeric SMILES CCOc1ccccc1OCC1CNCCO1
InChI InChI=1S/C13H19NO3/c1-2-15-12-5-3-4-6-13(12)17-10-11-9-14-7-8-16-11/h3-6,11,14H,2,7-10H2,1H3
InChI Key YWPHCCPCQOJSGZ-UHFFFAOYSA-N
Bioactivity Comments
Binds to NET with a Kd of 115 nM [3]. Binding affinity for SERT is >17 μM.