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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:41 UTC
HMDB IDHMDB15637
Secondary Accession NumbersNone
Metabolite Identification
Common NameVilazodone
DescriptionVilazodone is a novel compound with combined high affinity and selectivity for the 5-hydroxytryptamine (5-HT) transporter and 5-HT(1A) receptors. It has been shown to be equally efficacious as other antidepressants with similar gastrointestinal side effects and possibly with reduced sexual side effects and weight gain. Vilazodone is an antidepressant agent that can used as an alternative for patients who cannot tolerate therapy with other antidepressant classes such as selective serotonin reuptake inhibitors or serotonin norepinephrine reuptake inhibitors. Treatment should be titrated towards the target dose, which is 40mg per day.
Structure
Thumb
Synonyms
ValueSource
VilazodonaChEBI
VilazodonumChEBI
SB 659746aHMDB
Chemical FormulaC26H27N5O2
Average Molecular Weight441.5249
Monoisotopic Molecular Weight441.216475133
IUPAC Name5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide
Traditional Namevilazodone
CAS Registry Number163521-12-8
SMILES
NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1
InChI Identifier
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 KeyInChIKey=SGEGOXDYSFKCPT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Indole or derivatives
  • Indole
  • Benzofuran
  • Dialkylarylamine
  • Benzonitrile
  • Aralkylamine
  • N-alkylpiperazine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Furan
  • Tertiary aliphatic amine
  • Tertiary amine
  • Primary carboxylic acid amide
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidepressants
  • Selective Serotonin Reuptake Inhibitors (SSRIs)
  • Serotonin Agonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.23e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.71 m3·mol-1ChemAxon
Polarizability50.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06684
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06684
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06684
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5293518
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVilazodone
NuGOwiki LinkHMDB15637
Metagene LinkHMDB15637
METLIN IDNot Available
PubChem Compound6918314
PDB IDNot Available
ChEBI ID412971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [12183683 ]
  2. 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. [17351874 ]
  3. 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. [19499624 ]
  4. 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. [21323263 ]
  5. Traynor K: Vilazodone approved for major depression. Am J Health Syst Pharm. 2011 Mar 1;68(5):366. doi: 10.2146/news110009. [21330672 ]
  6. 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. [21527122 ]
  7. 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. [22935936 ]
  8. 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. [23578403 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. 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. [12183683 ]
  2. Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [15507223 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165
References
  1. 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. [12183683 ]
  2. Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [15507223 ]