Vilazodone

Vilazodone
Clinical data
Pronunciation/vɪˈlæzədn/
vi-LAZ-ə-dohn
Trade namesViibryd
Other namesEMD-68843; SB-659746A
AHFS/Drugs.comMonograph
MedlinePlusa611020
License data
Routes of
administration
By mouth
Drug classSerotonin modulator
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability72% (oral, with food)
MetabolismLiver via CYP3A4
Elimination half-life25 hours
ExcretionFaecal and renal
Identifiers
  • 5-(4-[4-(5-Cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H27N5O2
Molar mass441.535 g·mol−1
3D model (JSmol)
  • N#Cc5ccc4[nH]cc(CCCCN3CCN(c2ccc1oc(C(N)=O)cc1c2)CC3)c4c5
  • 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) Y
  • Key:SGEGOXDYSFKCPT-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Vilazodone, sold under the brand name Viibryd among others, is a medication used to treat major depressive disorder. It is classified as a serotonin modulator and is taken by mouth.

Common side effects include nausea, diarrhea, and trouble sleeping. Serious side effects may include increased suicidal thoughts or actions in those under the age of 25, serotonin syndrome, bleeding, mania, pancreatitis, and syndrome of inappropriate antidiuretic hormone secretion (SIADH). Vilazodone may cause less emotional blunting than typical selective serotonin reuptake inhibitors (SSRIs) and serotonin–norepinephrine reuptake inhibitors (SNRIs). A withdrawal syndrome may occur if the dose is rapidly decreased. Use during pregnancy and breastfeeding is not generally recommended. It is in the serotonin modulator class of medications and is believed to work both as an SSRI and activator of the 5-HT1A receptor.

Vilazodone was approved for medical use in the United States in 2011 and in Canada in 2018. In 2019, it was the 334th most commonly prescribed medication in the United States, with more than 900 thousand prescriptions. The drug lost patent protection in June 2022 for adults and in July 2023 for pediatrics. Generic versions have been approved by the US Food and Drug Administration.