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 313.93 41.74 82 979 11005 2346019
Hallucination 228.80 41.74 60 1001 8088 2348936
Serotonin syndrome 185.01 41.74 43 1018 3497 2353527
Abnormal dreams 178.10 41.74 39 1022 2419 2354605
Paraesthesia 158.35 41.74 57 1004 22031 2334993
Completed suicide 138.44 41.74 51 1010 20983 2336041
Diarrhoea 127.48 41.74 73 988 83491 2273533
Agitation 124.08 41.74 40 1021 11011 2346013
Dizziness 121.97 41.74 63 998 58602 2298422
Insomnia 117.90 41.74 48 1013 25739 2331285
Nausea 117.42 41.74 77 984 112112 2244912
Mania 113.46 41.74 27 1034 2413 2354611
Anxiety 111.88 41.74 48 1013 29311 2327713
Suicide attempt 103.19 41.74 35 1026 11247 2345777
Nightmare 102.31 41.74 27 1034 3670 2353354
Depression 94.11 41.74 42 1019 28090 2328934
Sleep paralysis 90.00 41.74 14 1047 121 2356903
Seizure 83.28 41.74 37 1024 24429 2332595
Off label use 77.68 41.74 51 1010 73547 2283477
Intentional overdose 72.56 41.74 27 1034 11294 2345730
Feeling abnormal 71.77 41.74 33 1028 23548 2333476
Tremor 63.10 41.74 29 1032 20632 2336392
Crying 62.07 41.74 19 1042 4377 2352647
Weight increased 57.89 41.74 28 1033 22309 2334715
Muscle twitching 52.34 41.74 15 1046 2750 2354274
Anger 49.25 41.74 14 1047 2493 2354531
Headache 46.84 41.74 39 1022 80140 2276884
Sleep terror 42.54 41.74 8 1053 226 2356798

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 168.69 57.91 45 455 8473 1737808
Serotonin syndrome 166.61 57.91 36 464 2752 1743529
Completed suicide 131.57 57.91 43 457 16269 1730012
Diarrhoea 79.01 57.91 42 458 53810 1692471
Mania 70.18 57.91 17 483 2116 1744165
Overdose 58.76 57.91 24 476 16677 1729604
Paraesthesia 58.21 57.91 21 479 10430 1735851

Pharmacologic Action:

SourceCodeDescription
ATC N06AX24 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35941 serotonergic agonist
CHEBI has role CHEBI:50949 serotonin uptake inhibitor
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

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(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
D000069503 MESH_DESCRIPTOR_UI
4030483 VUID
N0000182438 NUI
C1530072 UMLSCUI
D09698 KEGG_DRUG
715638004 SNOMEDCT_US
1086769 RXNORM
d07740 MMSL
4030483 VANDF
013753 NDDF
702837008 SNOMEDCT_US
6918314 PUBCHEM_CID
CHEBI:70707 CHEBI
CHEMBL439849 ChEMBL_ID
S239O2OOV3 UNII
7638 INN_ID
163521-08-2 SECONDARY_CAS_RN
DB06684 DRUGBANK_ID
CHEMBL1615374 ChEMBL_ID
7427 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 3 0456-1100 KIT 20 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 3 0456-1100 KIT 10 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 3 0456-1100 KIT 40 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 2 0456-1101 KIT 20 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 2 0456-1101 KIT 10 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1110 TABLET 10 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1120 TABLET 20 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 0456-1140 TABLET 40 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 55154-4624 TABLET 40 mg ORAL NDA 19 sections
VIIBRYD HUMAN PRESCRIPTION DRUG LABEL 1 55154-4627 TABLET 20 mg ORAL NDA 19 sections