Identification

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Name
Vilazodone
Accession Number
DB06684
Type
Small Molecule
Groups
Approved
Description

Vilazodone is a novel compound with combined high affinity and selectivity for the 5-hydroxytryptamine (5-HT) transporter and 5-HT(1A) receptorsLabel,2. Vilazodone may also be associated with less sexual dysfunction and weight gain3. Vilazodone was given FDA approval on January 21, 20115,2.

Structure
Thumb
Synonyms
  • Vilazodona
  • Vilazodone
  • Vilazodonum
External IDs
EMD 515259 / EMD-515259 / EMD-68843 / SB 659746A
Product Ingredients
IngredientUNIICASInChI Key
Vilazodone hydrochlorideU8HTX2GK8J163521-08-2RPZBRGFNBNQSOP-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ViibrydTablet20 mg/1OralCardinal Health2011-04-29Not applicableUs
ViibrydTablet, film coated40 mg/1OralTrovis Pharmaceuticals LLC2011-04-182011-04-18Us
ViibrydTablet40 mg/1OralAvera McKennan Hospital2015-03-102018-07-19Us69189 114020180907 15195 1fka5th
ViibrydTablet10 mgOralForest Laboratories2018-01-31Not applicableCanada
ViibrydTablet40 mg/1OralAllergan, Inc.2011-04-29Not applicableUs00456 1140 30 nlmimage10 c61de32f
ViibrydTablet, film coated20 mg/1OralTrovis Pharmaceuticals LLC2011-04-182011-04-18Us
ViibrydTablet20 mg/1OralAllergan, Inc.2011-04-29Not applicableUs00456 1120 30 nlmimage10 123d0918
ViibrydTablet, film coated10 mg/1OralTrovis Pharmaceuticals LLC2011-04-182011-04-18Us
ViibrydTablet10 mg/1OralAllergan, Inc.2011-04-29Not applicableUs
ViibrydTablet40 mgOralForest Laboratories2018-01-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1)KitOralAllergan, Inc.2011-04-29Not applicableUs
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1)KitOralTrovis Pharmaceuticals LLC2011-04-182011-04-18Us
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1)KitOralTrovis Pharmaceuticals LLC2011-04-182011-04-18Us
ViibrydVilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg)Kit; TabletOralForest LaboratoriesNot applicableNot applicableCanada
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1)KitOralAllergan, Inc.2011-04-29Not applicableUs
ViibrydVilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg) + Vilazodone hydrochloride (40 mg)Kit; TabletOralForest LaboratoriesNot applicableNot applicableCanada
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1)KitOralAllergan, Inc.2011-04-29Not applicableUs
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1)KitOralTrovis Pharmaceuticals LLC2011-04-182011-04-18Us
ViibrydVilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg) + Vilazodone hydrochloride (40 mg)Kit; TabletOralForest LaboratoriesNot applicableNot applicableCanada
ViibrydVilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1)KitOralAllergan, Inc.2011-04-29Not applicableUs
Categories
UNII
S239O2OOV3
CAS number
163521-12-8
Weight
Average: 441.5249
Monoisotopic: 441.216475133
Chemical Formula
C26H27N5O2
InChI Key
SGEGOXDYSFKCPT-UHFFFAOYSA-N
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)
IUPAC Name
5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide
SMILES
NC(=O)C1=CC2=CC(=CC=C2O1)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1

Pharmacology

Indication

Vilazodone is approved for treatment of major depressive disorderLabel,1,2.

Associated Conditions
Pharmacodynamics

Vilazodone increases serotonin levels in the brain by inhibiting the reuptake of serotonin while acting as a partial agonist on serotonin-1A receptorsLabel,1,3. Due to this activity vilazodone has sometimes been referred to as a selective partial agonist and reuptake inhibitor (SPARI)Label,3.

Mechanism of action

Vilazodone selectively inhibits serotonin reuptake in the central nervous system as well as acting as a partial agonist of 5HT-1A receptorsLabel,1. The exact mechanism for how these effects translate to its antidepressant effects are not knownLabel, though there is an association between these effects and antidepressive activity3.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
U5-hydroxytryptamine receptor 1A
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Vilazodone's bioavailability is 72% when taken with foodLabel,1.

Volume of distribution

Vilazodone's volume of distribution is unknown but largeLabel,1

Protein binding

96-99%Label,1,4.

Metabolism

Vilazodone is mainly metabolized by cytochrome P450(CYP)3A4 and also to a minor extent by CYP2C19 and CYP 2D6Label,1. Although the metabolic pathway for vilazodone has not been fully studied, a proposed mechanism for metabolism in rats was published in 20172.

Route of elimination

1% of the dose is recovered unchanged in the urine and 2% of the dose is recovered unchanged in the fecesLabel,1,4.

Half life

25 hoursLabel,1. Other studies show a half life of 24±5.2h with a single 40mg dose and 28.9±3.2h with repeated doses4.

Clearance

Clearance of vilazodone is 19.9-25.1L/h in patients with mild to moderate renal impairment compared to 26.4-26.9L/h in healthy controls4.

Toxicity

There is a lack of clinical studies of vilazodone in pregnancyLabel. Animal studies have shown the effects on offspring to be reduced fetal weight, increased mortality, delayed maturation, and decreased fertility in adulthood at doses well above the maximum recommended human doseLabel. Clinical cases of fetal and neonatal exposure to SSRIs and SNRIs have lead to a number of complications including respiratory distress, seizures, and temperature instabilityLabel. It is not know whether vilazodone is excreted in the breast milk of nursing mothers but animal studies show this is the case for ratsLabel. The risk and benefit of breast feeding while taking vilazodone for mother and child must be considered before a decision is madeLabel. Safety and effectiveness in pediatric patients has not been established in clinical trials though antidepressants are associated with an increased risk of suicidal thought and behaviour in patients under 24 yearsLabel. Clinical studies in geriatric patients showed to significant difference in response to vilazodone compared to younger patientsLabel. Geriatric patients should be started at a lower dose and titrated to an effective dose as they are more likely to have other comorbiditiesLabel. Dosage adjustments are not necessary for patients of different genders or with reduced hepatic and renal functionLabel.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Vilazodone is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Vilazodone is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Vilazodone.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Vilazodone.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Vilazodone.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Vilazodone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Vilazodone.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Vilazodone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Vilazodone.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Vilazodone.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Caution taking vilazodone with foods/herbal product with antiplatelet/anticoagulant properties
  • Gingko bilboa, ginger, garlic, green tea, licorice, horseradish

References

General References
  1. Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [PubMed:22346333]
  2. Chavan BB, Kalariya PD, Tiwari S, Nimbalkar RD, Garg P, Srinivas R, Talluri MVNK: Identification and characterization of vilazodone metabolites in rats and microsomes by ultrahigh-performance liquid chromatography/quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom. 2017 Dec 15;31(23):1974-1984. doi: 10.1002/rcm.7982. [PubMed:28875544]
  3. 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. [PubMed:23578403]
  4. Boinpally R, Alcorn H, Adams MH, Longstreth J, Edwards J: Pharmacokinetics of vilazodone in patients with mild or moderate renal impairment. Clin Drug Investig. 2013 Mar;33(3):199-206. doi: 10.1007/s40261-013-0061-5. [PubMed:23417352]
  5. FDA Drug Approval Package: Vilazodone [Link]
External Links
Human Metabolome Database
HMDB0015637
KEGG Drug
D09698
PubChem Compound
6918314
PubChem Substance
175427083
ChemSpider
5293518
BindingDB
50151982
ChEBI
70707
ChEMBL
CHEMBL439849
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vilazodone
ATC Codes
N06AX24 — Vilazodone
AHFS Codes
  • 28:16.04.24 — Serotonin Modulators
FDA label
Download (385 KB)
MSDS
Download (22.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
2CompletedPreventionMemory Disturbances1
2CompletedTreatmentMajor Depressive Disorder (MDD)2
2CompletedTreatmentMarijuana Dependence1
3CompletedTreatmentGeneralized Anxiety Disorder (GAD)2
3CompletedTreatmentMajor Depressive Disorder (MDD)7
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedTreatmentDepression / Post Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentMajor Depressive Disorder (MDD)4
4CompletedTreatmentSeparation Anxiety Disorder1
4TerminatedTreatmentMajor Depressive Disorder (MDD) / Sexual Dysfunctions1
4WithdrawnTreatmentAnxiety / Comorbidity / Major Depressive Disorder (MDD)1
Not AvailableCompletedTreatmentMenopausal Hot Flushes1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableUnknown StatusTreatmentSocial Anxiety Disorder (SAD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitOral
Kit; tabletOral
TabletOral10 mg
TabletOral10 mg/1
TabletOral20 mg
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral40 mg
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7834020No2010-11-162022-06-05Us
US8193195No2012-06-052022-06-05Us
US8236804No2012-08-072022-06-05Us
US8673921No2014-03-182022-06-05Us
US5532241No1996-07-022019-09-29Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.123 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
Polarizability50.03 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9959
Blood Brain Barrier+0.9694
Caco-2 permeable-0.6764
P-glycoprotein substrateSubstrate0.6362
P-glycoprotein inhibitor IInhibitor0.581
P-glycoprotein inhibitor IIInhibitor0.9022
Renal organic cation transporterNon-inhibitor0.527
CYP450 2C9 substrateNon-substrate0.9138
CYP450 2D6 substrateNon-substrate0.5431
CYP450 3A4 substrateSubstrate0.5983
CYP450 1A2 substrateNon-inhibitor0.5637
CYP450 2C9 inhibitorInhibitor0.5397
CYP450 2D6 inhibitorNon-inhibitor0.7021
CYP450 2C19 inhibitorInhibitor0.6998
CYP450 3A4 inhibitorNon-inhibitor0.6258
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8731
Ames testNon AMES toxic0.6088
CarcinogenicityNon-carcinogens0.9181
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6208 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8967
hERG inhibition (predictor II)Inhibitor0.87
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
N-arylpiperazines
Alternative Parents
3-alkylindoles / Benzofurans / 2-heteroaryl carboxamides / Furoic acid and derivatives / Dialkylarylamines / N-alkylpiperazines / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds
show 10 more
Substituents
N-arylpiperazine / 3-alkylindole / Benzofuran / Indole / Indole or derivatives / 2-heteroaryl carboxamide / Furoic acid or derivatives / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Aralkylamine
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, monocarboxylic acid amide, 1-benzofurans, indoles, nitrile, N-alkylpiperazine (CHEBI:70707)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin: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 t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [PubMed:22346333]
  2. 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. [PubMed:12183683]
  3. 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. [PubMed:15507223]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
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. [PubMed: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. [PubMed:15507223]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase 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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [PubMed:22346333]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase 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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [PubMed:22346333]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [PubMed:22346333]

Drug created on March 19, 2008 10:49 / Updated on August 21, 2019 23:47