vilazodone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
4223 163521-12-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • vilazodone
  • viibryd
  • vilazodone hydrochloride
  • vilazodone HCl
A benzofuran, indole, and piperazine derivative that functions as a SEROTONIN UPTAKE INHIBITOR and partial SEROTONIN 5-HT1 RECEPTOR AGONIST. It is used as an ANTIDEPRESSIVE AGENT.
  • Molecular weight: 441.54
  • Formula: C26H27N5O2
  • CLOGP: 4.08
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 102.29
  • ALOGS: -3.56
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 4.85 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.76 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.03 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 15.66 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 21, 2011 FDA FOREST LABS LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Suicidal ideation 215.35 22.41 107 4531 56275 46625149
Abnormal dreams 130.39 22.41 46 4592 10233 46671191
Hallucination 120.68 22.41 70 4568 49881 46631543
Serotonin syndrome 86.47 22.41 44 4594 24176 46657248
Sleep paralysis 77.43 22.41 16 4622 455 46680969
Paraesthesia 72.94 22.41 73 4565 117364 46564060
Agitation 72.77 22.41 53 4585 55362 46626062
Anxiety 71.49 22.41 89 4549 181868 46499556
Nightmare 70.65 22.41 34 4604 16564 46664860
Depression 66.48 22.41 83 4555 170021 46511403
Mania 64.37 22.41 28 4610 10818 46670606
Insomnia 51.31 22.41 72 4566 164852 46516572
Suicide attempt 47.21 22.41 41 4597 54995 46626429
Crying 41.58 22.41 26 4612 21115 46660309
Completed suicide 39.95 22.41 60 4578 145860 46535564
Tremor 39.71 22.41 53 4585 115586 46565838
Dizziness 38.40 22.41 96 4542 340318 46341106
Anger 37.86 22.41 20 4618 11832 46669592
Seizure 37.15 22.41 53 4585 123001 46558423
Muscle twitching 31.28 22.41 19 4619 14653 46666771
Sleep terror 29.14 22.41 8 4630 776 46680648
Feeling abnormal 28.09 22.41 47 4591 125013 46556411
Diarrhoea 26.07 22.41 117 4521 559485 46121939
Panic attack 25.71 22.41 19 4619 20223 46661201
Hypnagogic hallucination 24.59 22.41 5 4633 131 46681293
Off label use 23.67 22.41 87 4551 379754 46301670
Irritability 23.66 22.41 21 4617 28925 46652499

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Suicidal ideation 135.33 32.88 57 1648 36057 29914716
Serotonin syndrome 134.74 32.88 47 1658 17844 29932929
Completed suicide 88.16 32.88 60 1645 99432 29851341
Sexual dysfunction 49.85 32.88 17 1688 5984 29944789
Mania 46.37 32.88 18 1687 9136 29941637
Anxiety 45.67 32.88 39 1666 89832 29860941
Overdose 35.65 32.88 33 1672 84304 29866469

Pharmacologic Action:

SourceCodeDescription
ATC N06AX24 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants
MeSH PA D000928 Antidepressive Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D058825 Serotonin 5-HT1 Receptor Agonists
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D017367 Serotonin Uptake Inhibitors
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:35941 serotonergic agonists
CHEBI has role CHEBI:50949 serotonin reuptake inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Major depressive disorder indication 370143000
Suicidal thoughts contraindication 6471006
Bipolar disorder contraindication 13746004 DOID:3312
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Syndrome of inappropriate vasopressin secretion contraindication 55004003 DOID:3401
Blood coagulation disorder contraindication 64779008 DOID:1247
Hyponatremia contraindication 89627008
Seizure disorder contraindication 128613002
Suicidal contraindication 267073005
Serotonin syndrome contraindication 371089000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.56 acidic
pKa2 13.13 acidic
pKa3 8.58 Basic
pKa4 1.41 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
10MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL Jan. 31, 2023 INFORMATION ADDED TO THE LABELING REGARDING PEDIATRIC PATIENTS AGES 7 TO 17 YEARS OF AGE WITH MAJOR DEPRESSIVE DISORDER
20MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL Jan. 31, 2023 INFORMATION ADDED TO THE LABELING REGARDING PEDIATRIC PATIENTS AGES 7 TO 17 YEARS OF AGE WITH MAJOR DEPRESSIVE DISORDER
40MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL Jan. 31, 2023 INFORMATION ADDED TO THE LABELING REGARDING PEDIATRIC PATIENTS AGES 7 TO 17 YEARS OF AGE WITH MAJOR DEPRESSIVE DISORDER
10MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL July 31, 2023 PEDIATRIC EXCLUSIVITY
20MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL July 31, 2023 PEDIATRIC EXCLUSIVITY
40MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL July 31, 2023 PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent serotonin transporter Transporter INHIBITOR IC50 9.30 IUPHAR CHEMBL
5-hydroxytryptamine receptor 1A GPCR AGONIST Ki 9.70 IUPHAR CHEMBL
D(2) dopamine receptor GPCR AGONIST IC50 6.18 IUPHAR
Histamine H1 receptor GPCR AGONIST IC50 6.50 IUPHAR
5-hydroxytryptamine receptor 4 GPCR AGONIST IC50 6.60 IUPHAR
D(3) dopamine receptor GPCR AGONIST IC50 7.15 IUPHAR
Adrenergic receptor alpha-2 GPCR IC50 5.22 CHEMBL
Adrenergic receptor alpha-1 GPCR IC50 5.70 CHEMBL
5-hydroxytryptamine receptor 7 GPCR IC50 5.52 CHEMBL
D(3) dopamine receptor GPCR IC50 7.15 CHEMBL
Serotonin 3 (5-HT3) receptor Ion channel IC50 5.37 CHEMBL
5-hydroxytryptamine receptor 2C GPCR IC50 5.70 CHEMBL
5-hydroxytryptamine receptor 2A GPCR IC50 5.82 CHEMBL
Sodium-dependent serotonin transporter Transporter IC50 9.30 CHEMBL
D(4) dopamine receptor GPCR IC50 5.47 CHEMBL
5-hydroxytryptamine receptor 6 GPCR IC50 5.52 CHEMBL
5-hydroxytryptamine receptor 1B GPCR IC50 5.30 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 9.52 CHEMBL
5-hydroxytryptamine receptor 1D GPCR IC50 5.40 CHEMBL
5-hydroxytryptamine receptor 4 GPCR IC50 6.60 CHEMBL
D(2) dopamine receptor GPCR IC50 6.18 CHEMBL

External reference:

IDSource
4030483 VUID
N0000182438 NUI
D09698 KEGG_DRUG
163521-08-2 SECONDARY_CAS_RN
4030483 VANDF
4030484 VANDF
C2962550 UMLSCUI
CHEBI:70705 CHEBI
CHEMBL1615374 ChEMBL_ID
CHEMBL439849 ChEMBL_ID
D000069503 MESH_DESCRIPTOR_UI
7638 INN_ID
S239O2OOV3 UNII
6918313 PUBCHEM_CID
7427 IUPHAR_LIGAND_ID
DB06684 DRUGBANK_ID
1086768 RXNORM
179494 MMSL
27744 MMSL
d07740 MMSL
013753 NDDF
013754 NDDF
702837008 SNOMEDCT_US
715638004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1110 TABLET 10 mg ORAL NDA 31 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1120 TABLET 20 mg ORAL NDA 31 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1140 TABLET 40 mg ORAL NDA 31 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 55154-4624 TABLET 40 mg ORAL NDA 29 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 55154-4627 TABLET 20 mg ORAL NDA 29 sections