Vilazodone

Molecular structure of vilazodone
3D representation of a vilazodone molecule
Clinical data
Pronunciation	/vɪˈlæzədoʊn/ vi-LAZ-ə-dohn
Trade names	Viibryd
Other names	EMD-68843; SB-659746A
AHFS/Drugs.com	Monograph
MedlinePlus	a611020
License data	US DailyMed: Vilazodone
Routes of administration	By mouth
Drug class	Serotonin modulator[1]
ATC code	N06AX24 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[2] CA: ℞-only[3][4] US: ℞-only[5]
Pharmacokinetic data
Bioavailability	72% (oral, with food)[5]
Metabolism	Liver viaCYP3A4[5]
Eliminationhalf-life	25 hours[5]
Excretion	Faecal and renal[5]
Identifiers
IUPAC name 5-(4-[4-(5-Cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide
CAS Number	163521-12-8 N as HCl: 163521-08-2
PubChemCID	6918314 as HCl: 6918313
IUPHAR/BPS	7427
DrugBank	DB06684 as HCl: DBSALT000187
ChemSpider	5293518 Y as HCl: 5293517
UNII	S239O2OOV3 as HCl: U8HTX2GK8J
KEGG	D09698 Y as HCl: D09699
ChEBI	CHEBI:70707 N as HCl: CHEBI:70705
ChEMBL	ChEMBL439849 Y as HCl: ChEMBL1615374
PDB ligand	YG7 (PDBe,RCSB PDB)
CompTox Dashboard(EPA)	DTXSID80870086
Chemical and physical data
Formula	C26H27N5O2
Molar mass	441.535 g·mol−1
3D model (JSmol)	Interactive image
SMILES N#Cc5ccc4[nH]cc(CCCCN3CCN(c2ccc1oc(C(N)=O)cc1c2)CC3)c4c5
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) Y Key:SGEGOXDYSFKCPT-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Vilazodone, sold under the brand nameViibryd among others, is amedication used to treatmajor depressive disorder.^[1] It is classified as aserotonin modulator^[1] and is takenby mouth.^[1]

Its common side effects include nausea, diarrhea, and trouble sleeping.^[1] Serious side effects may include increasedsuicidal thoughts oractions in those under the age of 25,serotonin syndrome,bleeding, activation ofmania orhypomania,pancreatitis,seizures,angle-closure glaucoma, andsexual dysfunction.^[6]

Vilazodone may cause asyndrome of inappropriate antidiuretic hormone secretion (SIADH).^[1] Vilazodone may cause lessemotional blunting than typicalselective serotonin reuptake inhibitors (SSRIs) andserotonin–norepinephrine reuptake inhibitors (SNRIs).^[7] Awithdrawal syndrome may occur if the dose is rapidly decreased.^[1] Use duringpregnancy andbreastfeeding is not generally recommended.^[8] It is in theserotonin modulator class of medications and is believed to work both as an SSRI and activator of the5-HT_1A receptor.^[1]

Vilazodone was approved for medical use in the United States in 2011^[1] and in Canada in 2018.^[9] In 2019, it was the 334th most commonly prescribed medication in the United States, with more than 900 thousand prescriptions.^[10] The drug lost patent protection in June 2022 for adults and in July 2023 for pediatrics.^[11] Generic versions have been approved by the USFood and Drug Administration.^[12][13]

Seven controlled efficacy trials were conducted of vilazodone for treatment ofmajor depressive disorder.^[14] Five of these trials showed no significant influence of vilazodone overplacebo on depressive symptoms.^[14] In the remaining two trials, small but significant advantages of vilazodone over placebo were found.^[14] According to these two eight-week trials in adults, vilazodone has anantidepressant response after one week of treatment.^[15] After eight weeks it resulted in a 13% greater response than placebo.^[15]Remission rates, however, were not significantly different versus placebo.^[15]

According to the USFood and Drug Administration in 2011, "it is unknown whether vilazodone has any advantages compared to other drugs in the antidepressant class."^[16] A 2019 review stated that "present studies do not suggest the superiority of vilazodone compared with other antidepressants."^[17]

Development of vilazodone forgeneralized anxiety disorder has been stopped as of 2017.^[18] While there is tentative evidence of a small benefit in generalized anxiety disorder, there is a high rate of side effects.^[19]

In September 2016, the USFood and Drug Administration required a new warning to be added to theprescribing information related to a link between vilazodone andacute pancreatitis andsleep paralysis.^[20] In addition, othersleep disturbances such ashypnagogic hallucinations andsleep terrors can occur.^[21]

In July 2021, the US Food and Drug Administration required a new warning to be added to the prescription label that vilazodone may causesexual dysfunction.^[6]

The most commonadverse effects includenausea,diarrhea,vomiting, andinsomnia.^[5]

After a one-year,open-label study assessing the safety and tolerability of vilazodone in people with major depressive disorder, the most common adverse effects werediarrhea (35.7%),nausea (31.6%), andheadache (20.0%); greater than 90% of these adverse effects were mild or moderate.^[22][15] In randomized controlled trials, meanwhile, these rates were 28%, 23.4% and 13.3%, respectively.^[15] In contrast to otherselective serotonin reuptake inhibitors (SSRIs), initial trials showed that vilazodone did not causedecreased sexual desire/function, which often cause people to abandon their use.^{[23][unreliable medical source?]} Additionally, vilazodone may cause lessemotional blunting than typical SSRIs andserotonin–norepinephrine reuptake inhibitors (SNRIs).^[7]

Antidepressant exposure (including vilazodone) is associated with shorter average duration of pregnancy (by three days), increased risk of preterm delivery (by 55%), lower birth weight (by 75 g), and lowerApgar scores (by <0.4 points).^[24][25] It is uncertain whether there is an increased rate of septal heart defects among children whose mothers were prescribed an SSRI in early pregnancy.^[26][27]

Vilazodone acts as aserotonin reuptake inhibitor (IC₅₀ = 2.1 nM; K_i = 0.1 nM) and5-HT_1A receptorpartial agonist (IC₅₀ = 0.2 nM; IA = ~60–70%).^[15][28] It has negligibleaffinity for otherserotonin receptors such as5-HT_1D,5-HT_2A, and5-HT_2C,^[28][29] as well as the norepinephrine and dopamine transporters (K_i = 56 nM forNET and 37 nM forDAT).^[5] A small clinical study foundoccupancy of the 5-HT_1A receptor with vilazodone, whereas occupancy of theSERT by vilazodone in humans does not seem to have been studied.^[30][31][32]

Vilazodone is best absorbed with food and has abioavailability of 72% under fed conditions. TheC_max increased between 147 and 160% and theAUC increased between 64 and 85% of vilazodone when it was administered with either a fatty or light meal.^[33]

It was developed byMerck KGaA and licensed by Clinical Data, a biotech company purchased byForest Laboratories in 2011.^[34]

• 5-HT1A agonists
• Antidepressants
• Drugs developed by AbbVie
• Benzofuran-2-carboxamides
• Benzonitriles
• CYP2D6 inhibitors
• Drugs developed by Merck
• Experimental anxiolytics
• Indoles
• Piperazines
• Serotonin receptor agonists
• Serotonin reuptake inhibitors

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