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Identification
NameVilazodone
Accession NumberDB06684
TypeSmall Molecule
GroupsApproved
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
Vilazodona
Vilazodonum
External Identifiers
  • EMD-68843
  • SB 659746A
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ViibrydTablet10 mg/1OralAllergan, Inc.2011-04-29Not applicableUs
ViibrydTablet40 mg/1OralAvera Mc Kennan Hospital2015-03-10Not applicableUs
ViibrydTablet40 mgOralForest Laboratories Canada IncNot applicableNot applicableCanada
ViibrydTablet20 mg/1OralAllergan, Inc.2011-04-29Not applicableUs
ViibrydTablet10 mg/1OralAvera Mc Kennan Hospital2015-03-03Not applicableUs
ViibrydKitOralAllergan, Inc.2011-04-29Not applicableUs
ViibrydTablet40 mg/1OralAllergan, Inc.2011-04-29Not applicableUs
ViibrydTablet10 mgOralForest Laboratories Canada IncNot applicableNot applicableCanada
ViibrydKitOralAllergan, Inc.2011-04-29Not applicableUs
ViibrydTablet40 mg/1OralCardinal Health2011-04-29Not applicableUs
ViibrydTablet20 mgOralForest Laboratories Canada IncNot applicableNot applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
ViibrydForest Laboratories Canada Inc
Salts
Name/CASStructureProperties
Vilazodone hydrochloride
163521-08-2
Thumb
  • InChI Key: RPZBRGFNBNQSOP-UHFFFAOYSA-N
  • Monoisotopic Mass: 477.193152872
  • Average Mass: 477.986
DBSALT000187
Categories
UNIIS239O2OOV3
CAS number163521-12-8
WeightAverage: 441.5249
Monoisotopic: 441.216475133
Chemical FormulaC26H27N5O2
InChI KeySGEGOXDYSFKCPT-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=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1
Pharmacology
IndicationVilazodone is approved for treatment of acute episodes of major depression. Labeling of vilazodone describes an increased risk of suicidal thoughts in children, adolescents and young adults. The use of vilazodone in pediatrics is not indicated. Its use with monoamine oxidase inhibitors (MAOI) is contraindicated due to increased risk of serotonin syndome. Once the MAOI is discontinued, a 14-day washout period must pass before starting vilazodone.
Structured Indications
PharmacodynamicsVilazodone increases serotonin levels in the brain by inhibiting the reuptake of serotonin while acting as a partial agonist on serotonin-1A receptors. It has therefore been coined by scientists as a selective partial agonist and reuptake inhibitor (SPARI). Because of its partial agonist activity for serotonin-1A, vilazodone helps to reduce anxiety.
Mechanism of actionSince serotonin is believed to be one of the three main neurotransmitters that is low or imbalanced in patients with depression- pathways seeking to increase serotonin levels are targeted by pharmaceutical companies. As a selective serotonin reuptake inhibitor, vilazodone prevents serotonin from re-entering cell bodies. Hence, they will remain longer in the synapse. Vilazodone also has an inherent selectivity for serotonin-1A receptors, acting as a partial agonist which stimulates the production of serotonin. The end result is increased serotonin in the synaptic cleft, allowing serotonin to resume its action on nearby cells. The mechanism of the antidepressant effect of vilazodone is not fully understood, but is thought to be related to its enhancement of serotonergic activity in the CNS through selective inhibition of serotonin reuptake.
TargetKindPharmacological actionActionsOrganismUniProt ID
5-hydroxytryptamine receptor 1AProteinunknown
agonist
HumanP08908 details
Related Articles
AbsorptionVilazodone's absorption is improved when taken with food to 72%.
Volume of distributionNot Available
Protein binding96-99% protein bound
Metabolism

Major: CYP3A4. Minor: CYP2C19 and CYP2D6

Route of elimination1% recovered in urine. 2% unchanged in feces.
Half life25.4h
Clearance

21.1L/h

ToxicityVomiting, serotonin syndrome.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe metabolism of Vilazodone can be decreased when combined with 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE.Experimental
AbirateroneThe serum concentration of Vilazodone can be increased when it is combined with Abiraterone.Approved
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Vilazodone.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Aceprometazine.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Acetophenazine.Approved
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Vilazodone.Approved, Vet Approved
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Vilazodone.Approved, Investigational
AmiodaroneThe serum concentration of Vilazodone can be increased when it is combined with Amiodarone.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Vilazodone.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Vilazodone.Approved
AmperozideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Amperozide.Experimental
AprepitantThe serum concentration of Vilazodone can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Vilazodone.Approved, Investigational
ArtemetherThe metabolism of Vilazodone can be decreased when combined with Artemether.Approved
AsenapineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Asenapine.Approved
AtazanavirThe serum concentration of Vilazodone can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe serum concentration of Vilazodone can be increased when it is combined with Atomoxetine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Azaperone.Vet Approved
BenmoxinThe metabolism of Vilazodone can be decreased when combined with Benmoxin.Withdrawn
BenperidolThe risk or severity of adverse effects can be increased when Vilazodone is combined with Benperidol.Investigational
BetaxololThe metabolism of Vilazodone can be decreased when combined with Betaxolol.Approved
BexaroteneThe serum concentration of Vilazodone can be decreased when it is combined with Bexarotene.Approved, Investigational
BifeprunoxThe risk or severity of adverse effects can be increased when Vilazodone is combined with Bifeprunox.Investigational
BL-1020The risk or severity of adverse effects can be increased when BL-1020 is combined with Vilazodone.Investigational
BoceprevirThe serum concentration of Vilazodone can be increased when it is combined with Boceprevir.Approved
BortezomibThe serum concentration of Vilazodone can be increased when it is combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Vilazodone can be decreased when it is combined with Bosentan.Approved, Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Vilazodone is combined with Brexpiprazole.Approved
BromocriptineBromocriptine may increase the vasoconstricting activities of Vilazodone.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Vilazodone is combined with Bromperidol.Investigational
BupropionThe metabolism of Vilazodone can be decreased when combined with Bupropion.Approved
BuspironeBuspirone may increase the serotonergic activities of Vilazodone.Approved, Investigational
CabergolineCabergoline may increase the vasoconstricting activities of Vilazodone.Approved
CarbamazepineThe serum concentration of Vilazodone can be decreased when it is combined with Carbamazepine.Approved, Investigational
CariprazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Cariprazine.Approved
CaroxazoneThe metabolism of Vilazodone can be decreased when combined with Caroxazone.Withdrawn
CelecoxibThe metabolism of Vilazodone can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Vilazodone can be increased when it is combined with Ceritinib.Approved
ChloroquineThe metabolism of Vilazodone can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Vilazodone can be decreased when combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Chlorprothixene.Approved, Withdrawn
CholecalciferolThe metabolism of Vilazodone can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Vilazodone can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Vilazodone can be decreased when combined with Cinacalcet.Approved
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Vilazodone.Approved
ClarithromycinThe serum concentration of Vilazodone can be increased when it is combined with Clarithromycin.Approved
ClemastineThe serum concentration of Vilazodone can be increased when it is combined with Clemastine.Approved
ClobazamThe metabolism of Vilazodone can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Vilazodone.Approved, Vet Approved
ClotrimazoleThe serum concentration of Vilazodone can be increased when it is combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Vilazodone can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Vilazodone can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Vilazodone can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Vilazodone can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Vilazodone can be increased when it is combined with Crizotinib.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Cyamemazine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Vilazodone.Approved
CyclosporineThe serum concentration of Vilazodone can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Vilazodone can be decreased when it is combined with Dabrafenib.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Vilazodone is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Vilazodone.Investigational
DarifenacinThe metabolism of Vilazodone can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Vilazodone can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Vilazodone can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Vilazodone can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Vilazodone can be increased when it is combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Vilazodone.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Desvenlafaxine.Approved
DexamethasoneThe serum concentration of Vilazodone can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Vilazodone.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Vilazodone.Approved
DihydroergotamineThe serum concentration of Vilazodone can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Vilazodone can be increased when it is combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Vilazodone can be decreased when combined with Diphenhydramine.Approved
DolasetronDolasetron may increase the serotonergic activities of Vilazodone.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Vilazodone.Approved
DoxycyclineThe serum concentration of Vilazodone can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Vilazodone can be increased when it is combined with Dronedarone.Approved
DroperidolThe risk or severity of adverse effects can be increased when Vilazodone is combined with Droperidol.Approved, Vet Approved
DroxidopaVilazodone may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Vilazodone.Approved
EcopipamThe risk or severity of adverse effects can be increased when Vilazodone is combined with Ecopipam.Investigational
EfavirenzThe serum concentration of Vilazodone can be decreased when it is combined with Efavirenz.Approved, Investigational
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Vilazodone.Approved, Investigational
EliglustatThe metabolism of Vilazodone can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Vilazodone can be decreased when it is combined with Enzalutamide.Approved
Ergoloid mesylateErgoloid mesylate may increase the vasoconstricting activities of Vilazodone.Approved
ErgonovineErgonovine may increase the vasoconstricting activities of Vilazodone.Approved
ErgotamineErgotamine may increase the vasoconstricting activities of Vilazodone.Approved
ErythromycinThe serum concentration of Vilazodone can be increased when it is combined with Erythromycin.Approved, Vet Approved
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Vilazodone.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Vilazodone can be decreased when it is combined with Eslicarbazepine acetate.Approved
EtoperidoneEtoperidone may increase the serotonergic activities of Vilazodone.Approved
EtravirineThe serum concentration of Vilazodone can be decreased when it is combined with Etravirine.Approved
FencamfamineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Vilazodone.Approved, Illicit, Investigational, Vet Approved
FluconazoleThe serum concentration of Vilazodone can be increased when it is combined with Fluconazole.Approved
FluoxetineThe metabolism of Vilazodone can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Vilazodone is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Fluphenazine is combined with Vilazodone.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Fluspirilene.Approved
FluvoxamineThe serum concentration of Vilazodone can be increased when it is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Vilazodone can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Vilazodone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Vilazodone can be decreased when it is combined with Fosphenytoin.Approved
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Vilazodone.Approved, Investigational
FurazolidoneThe metabolism of Vilazodone can be decreased when combined with Furazolidone.Approved, Vet Approved
Fusidic AcidThe serum concentration of Vilazodone can be increased when it is combined with Fusidic Acid.Approved
GranisetronGranisetron may increase the serotonergic activities of Vilazodone.Approved, Investigational
HaloperidolThe metabolism of Vilazodone can be decreased when combined with Haloperidol.Approved
HydracarbazineThe metabolism of Vilazodone can be decreased when combined with Hydracarbazine.Approved
IdelalisibThe serum concentration of Vilazodone can be increased when it is combined with Idelalisib.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Iloperidone.Approved
ImatinibThe serum concentration of Vilazodone can be increased when it is combined with Imatinib.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Vilazodone.Approved
IndalpineIndalpine may increase the serotonergic activities of Vilazodone.Investigational, Withdrawn
IndinavirThe serum concentration of Vilazodone can be increased when it is combined with Indinavir.Approved
IproclozideThe metabolism of Vilazodone can be decreased when combined with Iproclozide.Withdrawn
IproniazidThe metabolism of Vilazodone can be decreased when combined with Iproniazid.Withdrawn
IsavuconazoniumThe serum concentration of Vilazodone can be increased when it is combined with Isavuconazonium.Approved, Investigational
IsocarboxazidThe metabolism of Vilazodone can be decreased when combined with Isocarboxazid.Approved
IsoniazidThe metabolism of Vilazodone can be decreased when combined with Isoniazid.Approved
IsradipineThe serum concentration of Vilazodone can be increased when it is combined with Isradipine.Approved
ItraconazoleThe serum concentration of Vilazodone can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Vilazodone can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Vilazodone can be increased when it is combined with Ketoconazole.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Vilazodone is combined with Levomilnacipran.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Vilazodone.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Lithium is combined with Vilazodone.Approved
LopinavirThe serum concentration of Vilazodone can be increased when it is combined with Lopinavir.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Vilazodone.Approved
LovastatinThe serum concentration of Vilazodone can be increased when it is combined with Lovastatin.Approved, Investigational
LoxapineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Loxapine.Approved
LuliconazoleThe serum concentration of Vilazodone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Vilazodone can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Vilazodone can be decreased when combined with Lumefantrine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Lurasidone.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Vilazodone.Approved
MebanazineThe metabolism of Vilazodone can be decreased when combined with Mebanazine.Withdrawn
MelperoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Melperone.Approved
MesoridazineThe risk or severity of adverse effects can be increased when Mesoridazine is combined with Vilazodone.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Vilazodone.Approved
MethotrimeprazineThe metabolism of Vilazodone can be decreased when combined with Methotrimeprazine.Approved
Methylene blueThe metabolism of Vilazodone can be decreased when combined with Methylene blue.Investigational
MetoclopramideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Metoclopramide.Approved, Investigational
MetoprololThe metabolism of Vilazodone can be decreased when combined with Metoprolol.Approved, Investigational
MifepristoneThe serum concentration of Vilazodone can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Vilazodone.Approved
MinaprineThe metabolism of Vilazodone can be decreased when combined with Minaprine.Approved
MirabegronThe metabolism of Vilazodone can be decreased when combined with Mirabegron.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Vilazodone.Approved
MitotaneThe serum concentration of Vilazodone can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Vilazodone can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Vilazodone can be decreased when it is combined with Modafinil.Approved, Investigational
MolindoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Molindone.Approved
MoricizineThe risk or severity of adverse effects can be increased when Moricizine is combined with Vilazodone.Approved, Withdrawn
NafcillinThe serum concentration of Vilazodone can be decreased when it is combined with Nafcillin.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Vilazodone.Approved, Investigational
NefazodoneThe serum concentration of Vilazodone can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Vilazodone can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Vilazodone can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Vilazodone can be decreased when it is combined with Nevirapine.Approved
NialamideThe metabolism of Vilazodone can be decreased when combined with Nialamide.Withdrawn
NicardipineThe metabolism of Vilazodone can be decreased when combined with Nicardipine.Approved
NilotinibThe serum concentration of Vilazodone can be increased when it is combined with Nilotinib.Approved, Investigational
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Vilazodone.Approved
OctamoxinThe metabolism of Vilazodone can be decreased when combined with Octamoxin.Withdrawn
OlanzapineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Olanzapine.Approved, Investigational
OlaparibThe serum concentration of Vilazodone can be increased when it is combined with Olaparib.Approved
OndansetronOndansetron may increase the serotonergic activities of Vilazodone.Approved
OsanetantThe risk or severity of adverse effects can be increased when Vilazodone is combined with Osanetant.Investigational
OsimertinibThe serum concentration of Vilazodone can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Vilazodone can be increased when it is combined with Palbociclib.Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Vilazodone.Approved, Investigational
PanobinostatThe serum concentration of Vilazodone can be increased when it is combined with Panobinostat.Approved, Investigational
PargylineThe metabolism of Vilazodone can be decreased when combined with Pargyline.Approved
ParoxetineThe metabolism of Vilazodone can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Vilazodone can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe serum concentration of Vilazodone can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PerazineThe risk or severity of adverse effects can be increased when Perazine is combined with Vilazodone.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Vilazodone is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Perphenazine is combined with Vilazodone.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Vilazodone.Approved
PhenelzineThe metabolism of Vilazodone can be decreased when combined with Phenelzine.Approved
PheniprazineThe metabolism of Vilazodone can be decreased when combined with Pheniprazine.Withdrawn
PhenobarbitalThe serum concentration of Vilazodone can be decreased when it is combined with Phenobarbital.Approved
PhenoxypropazineThe metabolism of Vilazodone can be decreased when combined with Phenoxypropazine.Withdrawn
PhenytoinThe serum concentration of Vilazodone can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PimozideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Pipotiazine.Approved
PirlindoleThe metabolism of Vilazodone can be decreased when combined with Pirlindole.Approved
PivhydrazineThe metabolism of Vilazodone can be decreased when combined with Pivhydrazine.Withdrawn
PosaconazoleThe serum concentration of Vilazodone can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of Vilazodone can be decreased when it is combined with Primidone.Approved, Vet Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Vilazodone.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with Vilazodone.Approved, Vet Approved
PromazineThe metabolism of Vilazodone can be decreased when combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Vilazodone.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Propericiazine.Approved
PropiopromazineThe risk or severity of adverse effects can be increased when Propiopromazine is combined with Vilazodone.Vet Approved
ProthipendylThe risk or severity of adverse effects can be increased when Vilazodone is combined with Prothipendyl.Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Vilazodone.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Quetiapine.Approved
QuinidineThe metabolism of Vilazodone can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Vilazodone can be decreased when combined with Quinine.Approved
RacloprideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Raclopride.Investigational
RanolazineThe serum concentration of Vilazodone can be increased when it is combined with Ranolazine.Approved, Investigational
RasagilineThe metabolism of Vilazodone can be decreased when combined with Rasagiline.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Remoxipride.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Reserpine.Approved
RifabutinThe serum concentration of Vilazodone can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Vilazodone can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Vilazodone can be decreased when it is combined with Rifapentine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Risperidone.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Vilazodone is combined with Ritanserin.Investigational
RitonavirThe serum concentration of Vilazodone can be increased when it is combined with Ritonavir.Approved, Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Vilazodone.Approved
RolapitantThe metabolism of Vilazodone can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Vilazodone can be decreased when combined with Ropinirole.Approved, Investigational
SafrazineThe metabolism of Vilazodone can be decreased when combined with Safrazine.Withdrawn
SaquinavirThe serum concentration of Vilazodone can be increased when it is combined with Saquinavir.Approved, Investigational
SelegilineThe metabolism of Vilazodone can be decreased when combined with Selegiline.Approved, Investigational, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Vilazodone is combined with Sertindole.Approved, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Vilazodone.Approved
SildenafilThe serum concentration of Vilazodone can be increased when it is combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Vilazodone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Vilazodone can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Vilazodone can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Vilazodone can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe serum concentration of Vilazodone can be increased when it is combined with Sulfisoxazole.Approved, Vet Approved
SulpirideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Sulpiride.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Vilazodone.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Vilazodone.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Vilazodone.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Vilazodone.Approved
TelaprevirThe serum concentration of Vilazodone can be increased when it is combined with Telaprevir.Approved
TelithromycinThe serum concentration of Vilazodone can be increased when it is combined with Telithromycin.Approved
TerbinafineThe metabolism of Vilazodone can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThiethylperazineThe risk or severity of adverse effects can be increased when Thiethylperazine is combined with Vilazodone.Withdrawn
ThioproperazineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Thioproperazine.Approved
ThioridazineThe metabolism of Vilazodone can be decreased when combined with Thioridazine.Approved
ThiothixeneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Thiothixene.Approved
TiaprideThe risk or severity of adverse effects can be increased when Vilazodone is combined with Tiapride.Investigational
TiclopidineThe serum concentration of Vilazodone can be increased when it is combined with Ticlopidine.Approved
TipranavirThe metabolism of Vilazodone can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Vilazodone can be decreased when it is combined with Tocilizumab.Approved
ToloxatoneThe metabolism of Vilazodone can be decreased when combined with Toloxatone.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Vilazodone.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe metabolism of Vilazodone can be decreased when combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe metabolism of Vilazodone can be decreased when combined with Tranylcypromine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Vilazodone.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Trifluoperazine is combined with Vilazodone.Approved
TriflupromazineThe risk or severity of adverse effects can be increased when Triflupromazine is combined with Vilazodone.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Vilazodone.Approved
TropisetronTropisetron may increase the serotonergic activities of Vilazodone.Investigational
VenlafaxineThe serum concentration of Vilazodone can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Vilazodone can be increased when it is combined with Verapamil.Approved
VoriconazoleThe serum concentration of Vilazodone can be increased when it is combined with Voriconazole.Approved, Investigational
VortioxetineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Vortioxetine.Approved
ZimelidineZimelidine may increase the serotonergic activities of Vilazodone.Withdrawn
ZiprasidoneThe serum concentration of Vilazodone can be increased when it is combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Vilazodone.Approved, Investigational
ZotepineThe risk or severity of adverse effects can be increased when Vilazodone is combined with Zotepine.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Vilazodone is combined with Zuclopenthixol.Approved, Investigational
Food Interactions
  • Caution taking vilazodone with foods/herbal product with antiplatelet/anticoagulant properties
  • Gingko bilboa, ginger, garlic, green tea, licorice, horseradish
References
Synthesis ReferenceNot Available
General References
  1. 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. [PubMed:21527122 ]
  2. Traynor K: Vilazodone approved for major depression. Am J Health Syst Pharm. 2011 Mar 1;68(5):366. doi: 10.2146/news110009. [PubMed:21330672 ]
  3. 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. [PubMed:21323263 ]
  4. 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. [PubMed:19499624 ]
  5. 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. [PubMed:17351874 ]
  6. 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 ]
  7. 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 ]
  8. 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. [PubMed:22935936 ]
External Links
ATC CodesN06AX24
AHFS Codes
  • 28:16.04.24
PDB EntriesNot Available
FDA labelDownload (164 KB)
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
KitOral
Kit; tabletOral
TabletOral10 mg
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral20 mg
TabletOral40 mg/1
TabletOral40 mg
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5532241 No1999-09-292019-09-29Us
US7834020 No2002-06-052022-06-05Us
US8193195 No2002-06-052022-06-05Us
US8236804 No2002-06-052022-06-05Us
US8673921 No2002-06-052022-06-05Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityAqueous solubility is 0.32 mg/mLNot Available
pKa7.1Not 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
Polarizability50.02 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
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

Targets

Kind
Protein
Organism
Human
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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
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
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Link [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
yes
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 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 an...
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular Weight:
70324.165 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 ]
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Drug created on March 19, 2008 10:49 / Updated on December 09, 2016 02:39