vilazodone   Click here for help

GtoPdb Ligand ID: 7427

Synonyms: EMD-515259 | EMD-68-843 | SB-659746-A | Viibryd®
Approved drug PDB Ligand
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
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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)
1. Dawson LA, Watson JM. (2009)
Vilazodone: a 5-HT1A receptor agonist/serotonin transporter inhibitor for the treatment of affective disorders.
CNS Neurosci Ther, 15 (2): 107-17. [PMID:19499624]
2. Heinrich T, Böttcher H, Gericke R, Bartoszyk GD, Anzali S, Seyfried CA, Greiner HE, Van Amsterdam C. (2004)
Synthesis and structure--activity relationship in a class of indolebutylpiperazines as dual 5-HT(1A) receptor agonists and serotonin reuptake inhibitors.
J Med Chem, 47 (19): 4684-92. [PMID:15341484]
3. Hughes ZA, Starr KR, Langmead CJ, Hill M, Bartoszyk GD, Hagan JJ, Middlemiss DN, Dawson LA. (2005)
Neurochemical evaluation of the novel 5-HT1A receptor partial agonist/serotonin reuptake inhibitor, vilazodone.
Eur J Pharmacol, 510 (1-2): 49-57. [PMID:15740724]
4. Zhu XY, Etukala JR, Eyunni SV, Setola V, Roth BL, Ablordeppey SY. (2012)
Benzothiazoles as probes for the 5HT1A receptor and the serotonin transporter (SERT): a search for new dual-acting agents as potential antidepressants.
Eur J Med Chem, 53: 124-32. [PMID:22520153]