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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: vilazodone

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
References
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]