Vilazodone (CHEM022352)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:29:32 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022352
Identification
Common NameVilazodone
ClassSmall Molecule
DescriptionA 1-benzofuran that is 5-(piperazin-1-yl}-1-benzofuran-2-carboxamide having a (5-cyanoindol-3-yl)butyl group attached at position N-4 on the piperazine ring. Used for the treatment of major depressive disorder.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
VilazodonaChEBI
VilazodonumChEBI
SB 659746aHMDB
HCL, VilazodoneHMDB
Hydrochloride, vilazodoneHMDB
2-Benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)HMDB
ViibrydHMDB
Vilazodone HCLHMDB
Vilazodone hydrochlorideHMDB
5-(4-(4-(5-Cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamideHMDB
Chemical FormulaC26H27N5O2
Average Molecular Mass441.525 g/mol
Monoisotopic Mass441.216 g/mol
CAS Registry Number163521-12-8
IUPAC Name5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide
Traditional Namevilazodone
SMILESNC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1
InChI IdentifierInChI=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 KeySGEGOXDYSFKCPT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • 3-alkylindole
  • Benzofuran
  • Indole
  • Indole or derivatives
  • 2-heteroaryl carboxamide
  • Furoic acid or derivatives
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aralkylamine
  • N-alkylpiperazine
  • Substituted pyrrole
  • Benzenoid
  • Furan
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Primary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP4.21ALOGPS
logP3.72ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.19ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.71 m³·mol⁻¹ChemAxon
Polarizability50.02 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-1892200000-e80db0623de8c5d5253bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0100900000-419df74d78f3394907e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0211900000-fc5409d02ddc3a074e29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ard-0930000000-ca1734ab642c796bbcafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-709b81c1b5cb6d2d8c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-1009600000-913d3342fc1dba5181aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9341100000-d9863664c2546f78ac6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-fb0afc1a6de498c1d581Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0201900000-7049e2907cdc39ce7fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pba-0931100000-c3a86c8646e2eb2feac2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0004900000-f0610bc45efeb8e8cd19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5006900000-70aadc301ad860239f5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-5598400000-9ca429b67adcdbb9ca8bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06684
HMDB IDHMDB0015637
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVilazodone
Chemspider ID5293518
ChEBI ID70707
PubChem Compound ID6918314
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19284933
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19499624
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19764890
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21323263
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21527122
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21672888
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21699273
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21738107
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21869687
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21951984
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22013560
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22106941
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22171584
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22284853
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22339643
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22414078
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22536068
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22860155
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22927207
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22935937
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22970859
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23033234
23. Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7.
24. de Paulis T: Drug evaluation: Vilazodone--a combined SSRI and 5-HT1A partial agonist for the treatment of depression. IDrugs. 2007 Mar;10(3):193-201.
25. Dawson LA, Watson JM: Vilazodone: a 5-HT1A receptor agonist/serotonin transporter inhibitor for the treatment of affective disorders. CNS Neurosci Ther. 2009 Summer;15(2):107-17.
26. Howland RH: Vilazodone: another novel atypical antidepressant drug. J Psychosoc Nurs Ment Health Serv. 2011 Mar;49(3):19-22. doi: 10.3928/02793695-20110203-98. Epub 2011 Feb 16.
27. Traynor K: Vilazodone approved for major depression. Am J Health Syst Pharm. 2011 Mar 1;68(5):366. doi: 10.2146/news110009.
28. Khan A, Cutler AJ, Kajdasz DK, Gallipoli S, Athanasiou M, Robinson DS, Whalen H, Reed CR: A randomized, double-blind, placebo-controlled, 8-week study of vilazodone, a serotonergic agent for the treatment of major depressive disorder. J Clin Psychiatry. 2011 Apr;72(4):441-7. doi: 10.4088/JCP.10m06596.
29. Dopheide JA: Vilazodone's comparative merits yet to be demonstrated. Am J Health Syst Pharm. 2012 Sep 15;69(18):1549. doi: 10.2146/ajhp110570.
30. Wang SM, Han C, Lee SJ, Patkar AA, Masand PS, Pae CU: A review of current evidence for vilazodone in major depressive disorder. Int J Psychiatry Clin Pract. 2013 Aug;17(3):160-9. doi: 10.3109/13651501.2013.794245. Epub 2013 May 29.