Identification
- Summary
Vilazodone is an antidepressant agent used for the treatment of major depressive disorder that targets the 5-HT transporter and 5-HT1A receptors.
- Brand Names
- Viibryd
- Generic Name
- Vilazodone
- DrugBank Accession Number
- DB06684
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Vilazodone (DB06684)
- Weight
- Average: 441.5249
Monoisotopic: 441.216475133 - Chemical Formula
- C26H27N5O2
- Synonyms
- Vilazodona
- Vilazodone
- Vilazodonum
- External IDs
- EMD 515259
- EMD-515259
- EMD-68843
- SB 659746A
Pharmacology
- Indication
Vilazodone is approved for treatment of major depressive disorder.Label,1,2
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Major depressive disorder •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ASodium-dependent serotonin transporter inhibitorHumans U5-hydroxytryptamine receptor 1A agonistHumans - 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
- 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.
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Vilazodone is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Vilazodone can be increased when it is combined with Abametapir. Abatacept The metabolism of Vilazodone can be increased when combined with Abatacept. Abiraterone The metabolism of Vilazodone can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Vilazodone. - Food Interactions
- Avoid alcohol.
- Avoid St. John's Wort.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Vilazodone hydrochloride U8HTX2GK8J 163521-08-2 RPZBRGFNBNQSOP-UHFFFAOYSA-N - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Viibryd Tablet 10 mg Oral Abbvie 2018-01-31 Not applicable Canada 
Viibryd Tablet 40 mg/1 Oral Allergan, Inc. 2011-04-29 Not applicable US 
Viibryd Tablet 40 mg/1 Oral Cardinal Health 107, LLC 2011-04-29 2024-04-30 US 
Viibryd Tablet, film coated 20 mg/1 Oral Trovis Pharmaceuticals LLC 2011-04-18 2011-04-18 US Viibryd Tablet 40 mg Oral Abbvie 2018-01-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vilazodone Tablet 20 mg/1 Oral Golden State Medical Supply, Inc. 2021-01-21 2024-05-31 US Vilazodone Tablet 20 mg/1 Oral Apotex Corp 2022-06-04 Not applicable US Vilazodone Tablet 10 mg/1 Oral Golden State Medical Supply, Inc. 2021-01-21 2024-02-29 US Vilazodone Tablet 40 mg/1 Oral Golden State Medical Supply, Inc. 2021-01-21 2024-07-31 US Vilazodone Tablet 10 mg/1 Oral Apotex Corp 2022-06-04 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Viibryd Vilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg) + Vilazodone hydrochloride (40 mg) Kit; Tablet Oral Forest Laboratories Not applicable Not applicable Canada Viibryd Vilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg) Kit; Tablet Oral Abbvie 2018-07-06 2023-07-20 Canada Viibryd Vilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1) Kit Oral Allergan, Inc. 2011-04-29 2016-08-31 US Viibryd Vilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1) Kit Oral Trovis Pharmaceuticals LLC 2011-04-18 2011-04-18 US Viibryd Vilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) Kit Oral Trovis Pharmaceuticals LLC 2011-04-18 2011-04-18 US
Categories
- ATC Codes
- N06AX24 — Vilazodone
- Drug Categories
- Agents that produce hypertension
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Benzofurans
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Indoles
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Piperazines
- Psychoanaleptics
- Psychotropic Drugs
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Agonists
- Serotonin Agents
- Serotonin antagonist and reuptake inhibitors (SARIs)
- Serotonin Modulators
- Serotonin Receptor Agonists
- Chemical TaxonomyProvided by Classyfire
- 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
- 2-heteroaryl carboxamide / 3-alkylindole / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzofuran / Carbonitrile show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- N-arylpiperazine, monocarboxylic acid amide, 1-benzofurans, indoles, nitrile, N-alkylpiperazine (CHEBI:70707)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- S239O2OOV3
- CAS number
- 163521-12-8
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 1086769
- ChEBI
- 70707
- ChEMBL
- CHEMBL439849
- ZINC
- ZINC000001542113
- PDBe Ligand
- YG7
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Vilazodone
- PDB Entries
- 7lwd
- FDA label
- Download (385 KB)
- MSDS
- Download (22.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Other Healthy Controls / Major Depressive Disorder (MDD) 1 4 Completed Treatment Depression / Post Traumatic Stress Disorder (PTSD) 1 4 Completed Treatment Major Depressive Disorder (MDD) 4 4 Completed Treatment Separation Anxiety Disorder 1 4 Terminated Treatment Major Depressive Disorder (MDD) / Sexual Dysfunctions 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral Kit; tablet Oral Tablet Oral 10 mg Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Tablet Oral 20 mg Tablet Oral 40 mg/1 Tablet Oral 40 mg Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 40 mg/1 Tablet, film coated Oral 10 mg Tablet, film coated Oral 20 mg Tablet, film coated Oral 40 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7834020 Yes 2010-11-16 2022-12-05 US US8193195 Yes 2012-06-05 2022-12-05 US US8236804 Yes 2012-08-07 2022-12-05 US US8673921 Yes 2014-03-18 2022-12-05 US US5532241 No 1996-07-02 2019-09-29 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.123 mg/mL ALOGPS logP 4.21 ALOGPS logP 3.72 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 14.19 Chemaxon pKa (Strongest Basic) 8.6 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 102.29 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 129.71 m3·mol-1 Chemaxon Polarizability 50.03 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9959 Blood Brain Barrier + 0.9694 Caco-2 permeable - 0.6764 P-glycoprotein substrate Substrate 0.6362 P-glycoprotein inhibitor I Inhibitor 0.581 P-glycoprotein inhibitor II Inhibitor 0.9022 Renal organic cation transporter Non-inhibitor 0.527 CYP450 2C9 substrate Non-substrate 0.9138 CYP450 2D6 substrate Non-substrate 0.5431 CYP450 3A4 substrate Substrate 0.5983 CYP450 1A2 substrate Non-inhibitor 0.5637 CYP450 2C9 inhibitor Inhibitor 0.5397 CYP450 2D6 inhibitor Non-inhibitor 0.7021 CYP450 2C19 inhibitor Inhibitor 0.6998 CYP450 3A4 inhibitor Non-inhibitor 0.6258 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8731 Ames test Non AMES toxic 0.6088 Carcinogenicity Non-carcinogens 0.9181 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6208 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8967 hERG inhibition (predictor II) Inhibitor 0.87
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0pb9-1892200000-e80db0623de8c5d5253b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0000900000-b7296c52e92303c27b43 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00dm-0003900000-eb92ab589376718266c6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0097-0201900000-a8eee8f3f272a9b91497 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-5009700000-4eef03aa94a42392c657 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6x-0981200000-127d97e11992d536148b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-1495400000-111188bd6b56494c80b6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 238.0315313 predictedDarkChem Lite v0.1.0 [M-H]- 202.66661 predictedDeepCCS 1.0 (2019) [M+H]+ 238.2635313 predictedDarkChem Lite v0.1.0 [M+H]+ 205.02461 predictedDeepCCS 1.0 (2019) [M+Na]+ 238.2641313 predictedDarkChem Lite v0.1.0 [M+Na]+ 211.11775 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at March 19, 2008 16:49 / Updated at January 02, 2024 23:48