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

Details

Stereochemistry ACHIRAL
Molecular Formula C26H27N5O2
Molecular Weight 441.5259
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VILAZODONE

SMILES

C(CCN1CCN(CC1)c2ccc3c(c2)cc(C(=N)O)o3)Cc4c[nH]c5ccc(cc45)C#N

InChI

InChIKey=SGEGOXDYSFKCPT-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C26H27N5O2
Molecular Weight 441.5259
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
0.5 nM [IC50]
0.200000000000000011 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIIBRYD

Approved Use

Indicated for the treatment of major depressive disorder (MDD)

Launch Date

1295568000000
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:
healthy, 1.8
Health Status: healthy
Age Group: 1.8
Sex: F
Sources:
Disc. AE: Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Serotonin syndrome
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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:
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
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
Disc. AE: Nausea, Anxiety...
AEs leading to
discontinuation/dose reduction:
Nausea (1.3%)
Anxiety (1%)
Sources:
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
Disc. AE: Tachycardia, Seizure...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Seizure
Serotonin syndrome
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:
healthy
Disc. AE: Syncope convulsive...
AEs leading to
discontinuation/dose reduction:
Syncope convulsive (1.78%)
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:
unhealthy
Disc. AE: Suicidal ideation, Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Serotonin syndrome
Neuroleptic malignant syndrome
Seizures
Bleeding
Hypomania
Hyponatremia
Sources:
80 mg 1 times / day multiple, oral
Studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
healthy
Disc. AE: Emesis, Palpitations...
AEs leading to
discontinuation/dose reduction:
Emesis (3.5%)
Palpitations (1.78%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Serotonin syndrome Disc. AE
920 mg single, oral
Overdose
Dose: 920 mg
Route: oral
Route: single
Dose: 920 mg
Sources:
healthy, 1.8
Health Status: healthy
Age Group: 1.8
Sex: F
Sources:
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
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:
unhealthy, 18 - 65
Health Status: unhealthy
Age Group: 18 - 65
Sex: M+F
Sources:
Seizure Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
Serotonin syndrome Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
Tachycardia Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
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:
healthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Palpitations 1.78%
Disc. AE
80 mg 1 times / day multiple, oral
Studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
healthy
Emesis 3.5%
Disc. AE
80 mg 1 times / day multiple, oral
Studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
healthy
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

PubMed

PubMed

TitleDatePubMed
A review of the clinical efficacy, safety and tolerability of the antidepressants vilazodone, levomilnacipran and vortioxetine.
2014 Dec
Issues encountered in recent attempts to develop novel antidepressant agents.
2015 May
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:29:38 UTC 2021
Edited
by admin
on Sat Jun 26 03:29:38 UTC 2021
Record UNII
S239O2OOV3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VILAZODONE
DASH   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
VILAZODONE [MI]
Common Name English
EMD-515259
Code English
2-BENZOFURANCARBOXAMIDE, 5-(4-(4-(5-CYANO-1H-INDOL-3-YL)BUTYL)-1-PIPERAZINYL)-
Systematic Name English
5-(4-(4-(5-CYANO-1H-INDOL-3-YL)BUTYL)PIPERAZIN-1-YL)BENZOFURAN-2-CARBOXAMIDE
Systematic Name English
VILAZODONE [MART.]
Common Name English
VILAZODONE [INN]
Common Name English
EMD 515259
Code English
VILAZODONE [VANDF]
Common Name English
5-(4-(4-(5-CYANOINDOL-3-YL)BUTYL)-1-PIPERAZINYL)-2-BENZOFURANCARBOXAMIDE
Systematic Name English
VILAZODONE [USAN]
Common Name English
EMD-68-843
Code English
VILAZODONE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
WHO-ATC N06AX24
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
LIVERTOX 1028
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
WHO-VATC QN06AX24
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
Code System Code Type Description
RXCUI
1086769
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY RxNorm
FDA UNII
S239O2OOV3
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
HSDB
8197
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL439849
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
EVMPD
SUB32166
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
MERCK INDEX
M11446
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY Merck Index
MESH
C494040
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
DRUG BANK
DB06684
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
CAS
163521-12-8
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
PUBCHEM
6918314
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
LACTMED
Vilazodone
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
IUPHAR
7427
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
INN
7638
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
WIKIPEDIA
VILAZODONE
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
NCI_THESAURUS
C90716
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
DRUG CENTRAL
4223
Created by admin on Sat Jun 26 03:29:38 UTC 2021 , Edited by admin on Sat Jun 26 03:29:38 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
In vitro studies have shown that vilazodone is a moderate inhibitor of CYP2C19 and CYP2D6
METABOLIC ENZYME -> SUBSTRATE
TARGET->PARTIAL AGONIST
EXCRETED UNCHANGED
FECAL; URINE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
In vitro studies have shown that vilazodone is a moderate inhibitor of CYP2C19 and CYP2D6
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC IV infusion

Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC