U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C26H27N5O2.ClH
Molecular Weight 477.986
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VILAZODONE HYDROCHLORIDE

SMILES

Cl.NC(=O)C1=CC2=C(O1)C=CC(=C2)N3CCN(CCCCC4=CNC5=CC=C(C=C45)C#N)CC3

InChI

InChIKey=RPZBRGFNBNQSOP-UHFFFAOYSA-N
InChI=1S/C26H27N5O2.ClH/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);1H

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9098681

Vilazodone is a serotonergic antidepressant. The mechanism of the antidepressant effect of vilazodone is not fully understood but is thought to be related to its inhancement of serotonergic activity in the CNS through selective inhibition of serotonin reuptake. Vilazodone is also a partial agonist at serotonergic 5-HT1A receptors; however, the net result of this action on serotonergic transmission and its role in vilazodone’s antidepressant effect are unknown. The side effects include activation of mania/hypomania in patients with bipolar disorder, seizures can occur with treatment in patients with a seizure disorder.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
0.5 nM [IC50]
0.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIIBRYD

Approved Use

Indicated for the treatment of major depressive disorder (MDD)

Launch Date

1.29556795E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
156 ng/mL
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
VILAZODONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1645 ng × h/mL
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
VILAZODONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
25 h
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
VILAZODONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
VILAZODONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
920 mg single, oral
Overdose
Dose: 920 mg
Route: oral
Route: single
Dose: 920 mg
Sources: Page: p.2
healthy, 1.8
n = 1
Health Status: healthy
Age Group: 1.8
Sex: F
Population Size: 1
Sources: Page: p.2
Disc. AE: Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Serotonin syndrome
Sources: Page: p.2
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 436
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 436
Sources: Page: p.25
Disc. AE: Palpitations, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Palpitations (0.92%)
Diarrhea (0.92%)
Nausea (0.46%)
Depression (0.46%)
Fatigue (0.46%)
Sources: Page: p.25
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources:
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.2%)
Sources:
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources: Page: p.25
Disc. AE: Nausea, Anxiety...
AEs leading to
discontinuation/dose reduction:
Nausea (1.3%)
Anxiety (1%)
Sources: Page: p.25
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources: Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources: Page: p.3
Disc. AE: Tachycardia, Seizure...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Seizure
Serotonin syndrome
Sources: Page: p.3
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources: Page: p.10, p.11
Disc. AE: Syncope convulsive...
AEs leading to
discontinuation/dose reduction:
Syncope convulsive (1.78%)
Sources: Page: p.10, p.11
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Disc. AE: Suicidal ideation, Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Serotonin syndrome
Neuroleptic malignant syndrome
Seizures
Bleeding
Hypomania
Hyponatremia
Sources: Page: p.1
80 mg 1 times / day multiple, oral (max)
Studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources: Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources: Page: p.10, p.11
Disc. AE: Emesis, Palpitations...
AEs leading to
discontinuation/dose reduction:
Emesis (3.5%)
Palpitations (1.78%)
Sources: Page: p.10, p.11
AEs

AEs

AESignificanceDosePopulation
Serotonin syndrome Disc. AE
920 mg single, oral
Overdose
Dose: 920 mg
Route: oral
Route: single
Dose: 920 mg
Sources: Page: p.2
healthy, 1.8
n = 1
Health Status: healthy
Age Group: 1.8
Sex: F
Population Size: 1
Sources: Page: p.2
Depression 0.46%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 436
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 436
Sources: Page: p.25
Fatigue 0.46%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 436
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 436
Sources: Page: p.25
Nausea 0.46%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 436
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 436
Sources: Page: p.25
Diarrhea 0.92%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 436
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 436
Sources: Page: p.25
Palpitations 0.92%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 436
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 436
Sources: Page: p.25
Diarrhea 1.2%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources:
Anxiety 1%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources: Page: p.25
Nausea 1.3%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.25
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources: Page: p.25
Seizure Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources: Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources: Page: p.3
Serotonin syndrome Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources: Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources: Page: p.3
Tachycardia Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources: Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources: Page: p.3
Syncope convulsive 1.78%
Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources: Page: p.10, p.11
Bleeding Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Hypomania Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Hyponatremia Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Neuroleptic malignant syndrome Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Seizures Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Serotonin syndrome Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Suicidal ideation Disc. AE
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources: Page: p.1
Palpitations 1.78%
Disc. AE
80 mg 1 times / day multiple, oral (max)
Studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources: Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources: Page: p.10, p.11
Emesis 3.5%
Disc. AE
80 mg 1 times / day multiple, oral (max)
Studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources: Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources: Page: p.10, p.11
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
moderate [IC50 2.8 uM]
moderate [Ki 7.37 uM]
no
no
no
no
no
no
no
no
no (co-administration study)
Comment: Human hepatocytes (two donors), Little/no increases were observed in mRNA expression.; Coadministration of vilazodone (20 mg QD for 10 days) with caffeine (100 mg QD on Day 10) to healthy subjects resulted in a small (9%) decrease in paraxanthine/caffeine plasma ratio (8-h post dose).
Page: 58, (ClinPharm) 18, 23, 47-49, 89-94
no
no (co-administration study)
Comment: Human hepatocytes (two donors), Little/no increases were observed in mRNA expression.; Coadministration of vilazodone (20 mg QD for 10 days) with flurbiprofen (50 mg QD on Day 10) to healthy subjects resulted no effect in CYP2C9 activity (4'-hydroxyflurbiprofen urinal recovery (0-8 hr)/flurbiprofen AUC0-8 (L/h)).
Page: 58, (ClinPharm) 18, 23, 47-49, 89-94
no
weak (co-administration study)
Comment: Human hepatocytes (two donors), Little/no increases were observed in mRNA expression.; Coadministration of vilazodone (20 mg QD for 10 days) with mephenytoin (100 mg QD on Day 10) to healthy subjects resulted in a small (11%) increase in mephenytoin biotransformation.
Page: 58, (ClinPharm) 18, 23, 47-49, 89-94
unlikely [IC50 >6.3 uM]
weak [IC50 68 uM]
weak [Ki 24 uM]
weak [Ki 81.7 uM]
weak
no (co-administration study)
Comment: 2.4-fold mRNA expression (60 hr incubation with human hepatocytes from two donors); Coadministration of vilazodone (20 mg QD for 10 days) with debrisoquine (10 mg QD on Day 10) to healthy subjects resulted in a small (10%) increase in 4'-hydroxydebrisoquine/debrisoquine total urinary recovery ratio (0-8 hr post dose).
Page: (ClinPharm) 18, 47-49, 89-94
weak
no (co-administration study)
Comment: 2.2-fold mRNA expression (60 hr incubation with human hepatocytes from two donors); Coadministration of vilazodone (20 mg QD for 10 days) with nifedipine (20 mg QD on Day 8) to healthy subjects resulted in no change in Nifedipine AUC0-inf and a small increase (13%) in Cmax.
Page: (ClinPharm) 18, 47-49, 89-94
weak
yes (co-administration study)
Comment: Coadministration of Vilazodone slightly increased Digoxin (P-gp substrate) AUC and Cmax (less than 25%).
Page: (Label) 12
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
major
yes (co-administration study)
Comment: Ketoconazole (200 mg QD for 13 days), a strong CYP3A4 inhibitor, increased vilazodone (5 mg or 10 mg QD on Day 4) systemic exposure (AUC0-t) by 42% (5 mg), 51% (10 mg), and Cmax by 48% (5 mg), 38% (10 mg), Human liver microsomes (specific inhibitor: troleandomycin 50 mcM)
Page: 58, (ClinPharm) 14, 18, 21, 22, 23, 37-39, 82-84
minor
minor
minor
unlikely
unlikely
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Efficacy and safety of vilazodone in major depressive disorder: a randomized, double-blind, placebo-controlled trial.
2014 Nov
Patents

Sample Use Guides

Recommended target dosage: 20 mg to 40 mg once daily with food. To titrate: start with initial dosage of 10 mg once daily for 7 days, followed by 20 mg once daily. The dose may be increased up to 40 mg once daily after a minimum of 7 days between dosage increases. Prior to initiating VIIBRYD, screen for bipolar disorder.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
VILAZODONE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
VILAZODONE HYDROCHLORIDE [MART.]
Common Name English
5-{4-[4-(5-Cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxamide monohydrochloride
Systematic Name English
EMD 68 843
Code English
VILAZODONE HCL
Common Name English
SB-659746-A
Code English
VILAZODONE HYDROCHLORIDE [VANDF]
Common Name English
Vilazodone hydrochloride [WHO-DD]
Common Name English
VILAZODONE HYDROCHLORIDE [USAN]
Common Name English
2-BENZOFURANCARBOXAMIDE, 5-(4-(4-(5-CYANO-1H-INDOL-3-YL)BUTYL)-1-PIPERAZINYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
VILAZODONE HYDROCHLORIDE [MI]
Common Name English
EMD-68843
Code English
VIIBRYD
Common Name English
SB659746-A
Code English
VILAZODONE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
Code System Code Type Description
CHEBI
70705
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
CAS
163521-08-2
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
DAILYMED
U8HTX2GK8J
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
MERCK INDEX
m11446
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL439849
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
SMS_ID
100000124535
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
USAN
WW-102
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID80936833
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
RXCUI
1086768
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C90717
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
DRUG BANK
DBSALT000187
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
EVMPD
SUB32288
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
FDA UNII
U8HTX2GK8J
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY
PUBCHEM
6918313
Created by admin on Fri Dec 15 15:41:18 UTC 2023 , Edited by admin on Fri Dec 15 15:41:18 UTC 2023
PRIMARY