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

Details

Stereochemistry ACHIRAL
Molecular Formula C26H27N5O2
Molecular Weight 441.5249
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VILAZODONE

SMILES

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

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 441.5249
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

CNS Activity

Originator

Approval Year

2011
587
Targets

Targets

Primary TargetPharmacologyConditionPotency
Sodium-dependent serotonin transporter
40
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 0.5 nM [IC50]
Agonist
2678
 0.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
VIIBRYD

Approved Use

Indicated for the treatment of major depressive disorder (MDD)

Launch Date

1.29556795E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
156 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022567s021lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022567s021lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022567s021lbl.pdf
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022567s021lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/33158691
Page: p.2
healthy, 1.8
n = 1
Health Status: healthy
Age Group: 1.8
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/33158691
Page: p.2
Disc. AE: Serotonin syndrome...
AEs leading to
discontinuation/dose reduction:
Serotonin syndrome
Sources:
https://pubmed.ncbi.nlm.nih.gov/33158691
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources:
https://pubmed.ncbi.nlm.nih.gov/27738360
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
Page: p.25
Disc. AE: Nausea, Anxiety...
AEs leading to
discontinuation/dose reduction:
Nausea (1.3%)
Anxiety (1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/27738360
Page: p.25
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
Disc. AE: Tachycardia, Seizure...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Seizure
Serotonin syndrome
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
Disc. AE: Syncope convulsive...
AEs leading to
discontinuation/dose reduction:
Syncope convulsive (1.78%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
Disc. AE: Emesis, Palpitations...
AEs leading to
discontinuation/dose reduction:
Emesis (3.5%)
Palpitations (1.78%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/33158691
Page: p.2
healthy, 1.8
n = 1
Health Status: healthy
Age Group: 1.8
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/33158691
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
unhealthy, 18 - 65
n = 599
Health Status: unhealthy
Condition: Major depressive disorder
Age Group: 18 - 65
Sex: M+F
Population Size: 599
Sources:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
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:
https://pubmed.ncbi.nlm.nih.gov/27738360
Page: p.25
Seizure Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
Serotonin syndrome Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
Tachycardia Disc. AE
840 mg single, oral
Overdose
Dose: 840 mg
Route: oral
Route: single
Dose: 840 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
Page: p.3
healthy, 3
n = 1
Health Status: healthy
Age Group: 3
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/31777303
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Major depressive disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022567s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
healthy
n = 56
Health Status: healthy
Population Size: 56
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000OtherR.pdf
Page: p.10, p.11
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inducer
781

inhibitor
1587
substrate
1037

inducer
389

inhibitor
1767
substrate
1217

inducer
97

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
810

CYP1A2
1524

CYP2C19
1478

CYP2E1
882

CYP2C8
911

P-gp
1461
CYP2C19
991

CYP2C8
693

CYP1A2
1054

CYP2A6
543

CYP2E1
667
CYP1A1
108

CYP1A2
701

CYP2A6
79

CYP2C19
293

CYP2E1
128

CYP3A5
76

CYP2C8
168
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1891
 moderate [IC50 2.8 uM]
CYP2C19
1553
 moderate [Ki 7.37 uM]
CYP1A1
218
 no
CYP2A6
739
 no
CYP2B6
1001
 no
CYP2C8
965
 no
CYP2E1
970
 no
CYP2E1
970
 no
CYP3A5
130
 no
CYP1A2
1692
 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
CYP2C9
1819
 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
CYP2C19
1553
 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
CYP2C8
965
 unlikely [IC50 >6.3 uM]
CYP3A4
1925
 weak [IC50 68 uM]
CYP2C9
1819
 weak [Ki 24 uM]
CYP1A2
1692
 weak [Ki 81.7 uM]
CYP2D6
1891
 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
CYP3A4
1925
 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
P-gp
1650
 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
CYP2C8
693
 likely
CYP2C9
1037
 likely
CYP3A4
1737
 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
CYP2C19
991
 minor
CYP2D6
1217
 minor
CYP2E1
667
 minor
CYP1A2
1054
 unlikely
CYP2A6
543
 unlikely
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:70707
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:70707
ChemicalBook
CB31011682
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB31011682
MolPort
MolPort-005-933-319
https://www.molport.com/shop/molecule-link/MolPort-005-933-319
ZINC
ZINC000001542113
http://zinc15.docking.org/substances/ZINC000001542113
eMolecules
36473276
https://www.emolecules.com/cgi-bin/more?vid=36473276
PubMed

PubMed

TitleDatePubMed
Patents

Patents

07381726
2
07834020
2
07981894
2
08193195
2
08236804
2
08318744
2
08673921
2
20040014771
2
JP2003500441A
2
JP2004513916A
2
JP2010132687A
2
JP2010132688A
2
JP2011148799A
2

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:47:34 UTC 2023
Edited
by admin
on Fri Dec 15 15:47:34 UTC 2023
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
EMD 68843 BASE
Code English
5-(4-(4-(5-CYANOINDOL-3-YL)BUTYL)-1-PIPERAZINYL)-2-BENZOFURANCARBOXAMIDE
Systematic Name English
Vilazodone [WHO-DD]
Common Name English
VILAZODONE [USAN]
Common Name English
EMD-68843 BASE
Common Name English
EMD-68-843
Code English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
WHO-ATC N06AX24
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
LIVERTOX NBK548223
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
WHO-VATC QN06AX24
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
Code System Code Type Description
RXCUI
1086769
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY RxNorm
FDA UNII
S239O2OOV3
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
CHEBI
70707
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
HSDB
8197
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL439849
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
EVMPD
SUB32166
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
MERCK INDEX
m11446
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY Merck Index
MESH
C494040
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
DRUG BANK
DB06684
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
CAS
163521-12-8
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
DAILYMED
S239O2OOV3
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
SMS_ID
100000124411
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
PUBCHEM
6918314
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
LACTMED
Vilazodone
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
IUPHAR
7427
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
INN
7638
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
WIKIPEDIA
VILAZODONE
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
USAN
WW-101
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID80870086
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
NCI_THESAURUS
C90716
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
DRUG CENTRAL
4223
Created by admin on Fri Dec 15 15:47:34 UTC 2023 , Edited by admin on Fri Dec 15 15:47:34 UTC 2023
PRIMARY
Related Record Type Details
Structure of VILAZODONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> INHIBITOR
In vitro studies have shown that vilazodone is a moderate inhibitor of CYP2C19 and CYP2D6
LIVER CARBOXYLESTERASE 1
METABOLIC ENZYME -> SUBSTRATE
5-HYDROXYTRYPTAMINE RECEPTOR 1A
TARGET->PARTIAL AGONIST
Structure of VILAZODONE
EXCRETED UNCHANGED
FECAL; URINE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
MINOR
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MINOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 2C19
METABOLIC ENZYME -> INHIBITOR
In vitro studies have shown that vilazodone is a moderate inhibitor of CYP2C19 and CYP2D6
Related Record Type Details
Structure of .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 3-(4-(4-(2-(AMINOCARBONYL)-2,3-DIHYDRO-5-BENZOFURANYL)-1-PIPERAZINYL)BUTYL)-5-CYANO-2,3-DIHYDRO-1H-INDOL-6-YL
METABOLITE -> PARENT
Structure of VILAZODONE CARBOXYLIC ACID
METABOLITE INACTIVE -> PARENT
Structure of 2-BENZOFURANCARBOXAMIDE, 5-(4-(4-(5-CYANO-6-HYDROXY-1H-INDOL-3-YL)BUTYL)-1-PIPERAZINYL)-
METABOLITE -> PARENT
Structure of 5-CYANOINDOLE-3-BUTANOIC ACID
METABOLITE -> PARENT
Structure of 5-(4-(4-(5-CYANO-1H-INDOL-3-YL)-4-HYDROXY-BUTYL)PIPERAZIN-1-YL)BENZOFURAN-2-CARBOXAMIDE
METABOLITE -> PARENT
Structure of 5-(4-(4-(5-CYANO-6,7-DIHYDROXY-6,7-DIHYDRO-1H-INDOL-3-YL)BUTYL)PIPERAZIN-1-YL)BENZOFURAN-2-CARBOXAMIDE
METABOLITE -> PARENT
Related Record Type Details
Structure of VILAZODONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC IV infusion

Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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