vilazodone   Click here for help

GtoPdb Ligand ID: 7427

Synonyms: EMD-515259 | EMD-68-843 | SB-659746-A | Viibryd®
Approved drug
vilazodone is an approved drug (FDA (2011))
Compound class: Synthetic organic
Comment: Note that the USAN (United States Adopted Name) refers to the hydrochloride salt which has PubChem CID 6918313.
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View more information in the IUPHAR Pharmacology Education Project: vilazodone

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 102.29
Molecular weight 441.22
XLogP 3.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#Cc1ccc2c(c1)c(CCCCN1CCN(CC1)c1ccc3c(c1)cc(o3)C(=O)N)c[nH]2
Isomeric SMILES N#Cc1ccc2c(c1)c(CCCCN1CCN(CC1)c1ccc3c(c1)cc(o3)C(=O)N)c[nH]2
InChI InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)
InChI Key SGEGOXDYSFKCPT-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT1A receptor Primary target of this compound Hs Agonist Partial agonist 9.7 pKi - 1
pKi 9.7 (Ki 2x10-10 M) [1]
Description: Binding of vilazodone to human 5-HT1A receptors against [3H]8-OH-DPAT (DPAT)
5-HT1A receptor Primary target of this compound Hs Agonist Partial agonist 9.5 pIC50 - 2
pIC50 9.5 (IC50 3x10-10 M) [2]
D3 receptor Hs Agonist Agonist 7.2 pIC50 - 2
pIC50 7.2 (IC50 7.1x10-8 M) [2]
5-HT4 receptor Hs Agonist Agonist 6.6 pIC50 - 2
pIC50 6.6 (IC50 2.52x10-7 M) [2]
H1 receptor Hs Agonist Agonist 6.5 pIC50 - 2
pIC50 6.5 (IC50 3.17x10-7 M) [2]
D2 receptor Hs Agonist Agonist 6.2 pIC50 - 2
pIC50 6.2 (IC50 6.66x10-7 M) [2]
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 8.8 – 9.3 pIC50 - 1-2
pIC50 8.8 – 9.3 (IC50 1.58x10-9 – 5x10-10 M) [1-2]