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 233.06 21.22 114 4973 60397 53283582
Abnormal dreams 134.67 21.22 47 5040 10554 53333425
Hallucination 118.44 21.22 70 5017 53768 53290211
Persistent genital arousal disorder 96.96 21.22 18 5069 301 53343678
Serotonin syndrome 90.34 21.22 46 5041 26360 53317619
Anxiety 80.10 21.22 96 4991 196608 53147371
Depression 78.93 21.22 92 4995 182960 53161019
Sleep paralysis 74.49 21.22 16 5071 574 53343405
Nightmare 72.82 21.22 35 5052 17716 53326263
Paraesthesia 72.18 21.22 74 5013 127441 53216538
Agitation 72.02 21.22 53 5034 58573 53285406
Mania 63.13 21.22 28 5059 11801 53332178
Insomnia 53.80 21.22 77 5010 186995 53156984
Suicide attempt 46.69 21.22 41 5046 58127 53285852
Completed suicide 45.88 21.22 61 5026 138140 53205839
Dizziness 41.60 21.22 102 4985 372157 52971822
Crying 41.32 21.22 26 5061 22236 53321743
Anger 40.65 21.22 21 5066 12369 53331610
Seizure 39.69 21.22 55 5032 129454 53214525
Tremor 39.43 21.22 54 5033 125682 53218297
Muscle twitching 32.54 21.22 20 5067 16406 53327573
Feeling abnormal 32.14 21.22 51 5036 135250 53208729
Sleep terror 28.92 21.22 8 5079 832 53343147
Panic attack 27.71 21.22 20 5067 21398 53322581
Withdrawal syndrome 27.22 21.22 19 5068 19282 53324697
Irritability 27.21 21.22 23 5064 30930 53313049
Diarrhoea 25.34 21.22 122 4965 625424 52718555
Hypnagogic hallucination 24.17 21.22 5 5082 149 53343830
Nausea 23.47 21.22 137 4950 755954 52588025

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 144.48 31.84 60 1724 38023 32473719
Serotonin syndrome 141.06 31.84 49 1735 19068 32492674
Completed suicide 96.63 31.84 61 1723 92456 32419286
Mania 53.30 31.84 20 1764 9612 32502130
Sexual dysfunction 49.68 31.84 17 1767 6272 32505470
Anxiety 48.76 31.84 41 1743 95964 32415778
Overdose 37.74 31.84 34 1750 87043 32424699
Partial seizures 31.91 31.84 11 1773 4139 32507603

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
10MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 7834020 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
10MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 8193195 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
10MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 8236804 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
20MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 7834020 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
20MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 8193195 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
20MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 8236804 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
40MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 7834020 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
40MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 8193195 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)
40MG VIIBRYD ALLERGAN N022567 Jan. 21, 2011 RX TABLET ORAL 8236804 June 5, 2022 TREATMENT OF MAJOR DEPRESSIVE DISORDER (MDD)

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(3) dopamine receptor GPCR AGONIST IC50 7.15 IUPHAR
Histamine H1 receptor GPCR AGONIST IC50 6.50 IUPHAR
5-hydroxytryptamine receptor 4 GPCR AGONIST IC50 6.60 IUPHAR
Adrenergic receptor alpha-2 GPCR IC50 5.22 CHEMBL
D(2) dopamine receptor GPCR AGONIST IC50 6.18 IUPHAR
Adrenergic receptor alpha-1 GPCR IC50 5.70 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 5.41 CHEMBL
5-hydroxytryptamine receptor 1B GPCR IC50 5.30 CHEMBL
D(2) dopamine receptor GPCR IC50 6.18 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 9.52 CHEMBL
Sodium-dependent serotonin transporter Transporter IC50 9.30 CHEMBL
5-hydroxytryptamine receptor 2A GPCR IC50 5.82 CHEMBL
5-hydroxytryptamine receptor 7 GPCR IC50 5.52 CHEMBL
Acetylcholinesterase Enzyme IC50 4.67 CHEMBL
5-hydroxytryptamine receptor 2C GPCR IC50 5.70 CHEMBL
5-hydroxytryptamine receptor 4 GPCR IC50 6.60 CHEMBL
D(3) dopamine receptor GPCR IC50 7.15 CHEMBL
5-hydroxytryptamine receptor 1D GPCR IC50 5.40 CHEMBL
D(4) dopamine receptor GPCR IC50 5.47 CHEMBL
5-hydroxytryptamine receptor 6 GPCR IC50 5.52 CHEMBL
Serotonin 3 (5-HT3) receptor Ion channel IC50 5.37 CHEMBL

External reference:

IDSource
4030483 VUID
N0000182438 NUI
D09698 KEGG_DRUG
163521-08-2 SECONDARY_CAS_RN
4030483 VANDF
4030484 VANDF
C1530072 UMLSCUI
CHEBI:70707 CHEBI
YG7 PDB_CHEM_ID
CHEMBL439849 ChEMBL_ID
CHEMBL1615374 ChEMBL_ID
D000069503 MESH_DESCRIPTOR_UI
DB06684 DRUGBANK_ID
7427 IUPHAR_LIGAND_ID
7638 INN_ID
S239O2OOV3 UNII
6918314 PUBCHEM_CID
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 32 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1120 TABLET 20 mg ORAL NDA 32 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1140 TABLET 40 mg ORAL NDA 32 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