VILAZODONE HYDROCHLORIDE

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022567s019lbl.pdf
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

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium-dependent serotonin transporter 40 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12183683	Inhibitor 8297		0.5 nM [IC50]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022567s019lbl.pdf	Agonist 2678		0.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022567s019lbl.pdf	Primary		Approved 8429	VIIBRYD Approved Use Indicated for the treatment of major depressive disorder (MDD) Launch Date 2011

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inducer 781 inhibitor 1587	substrate 1037 inducer 389 inhibitor 1767	substrate 1217 inducer 97 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other 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

Target	Modality	Activity	Clinical evidence
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=40, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=42 Page: 58, (ClinPharm) 19, 22-23, 37-40, 90	moderate [IC50 2.8 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=42 Page: 58, (ClinPharm) 19, 23, 37-39, 41-42, 90	moderate [Ki 7.37 uM]
CYP1A1 218	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49 Page: 58, (ClinPharm) 23, 47-49	no
CYP2A6 739	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49 Page: 58, (ClinPharm) 23	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49 Page: 58, (ClinPharm) 23, 47-49	no
CYP2C8 965	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=18 Page: (ClinPharm) 18	no
CYP2E1 970	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49 Page: 58, (ClinPharm) 18, 23, 47-49	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58 Page: 58.0	no
CYP3A5 130	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49 Page: 58, (ClinPharm) 23, 47-49	no
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=92 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 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). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=92 Page: 58, (ClinPharm) 18, 23, 47-49, 89-94
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=93 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)). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=93 Page: 58, (ClinPharm) 18, 23, 47-49, 89-94
CYP2C19 1553	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=93 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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=23, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=93 Page: 58, (ClinPharm) 18, 23, 47-49, 89-94
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=19, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=46 Page: (ClinPharm) 16, 19, 42-45, 45-47, 90	unlikely [IC50 >6.3 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=22, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=40 Page: 58, (ClinPharm) 22, 37-40, 42-45	weak [IC50 68 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=41 Page: 58, (ClinPharm) 22-23, 41-42, 90	weak [Ki 24 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=41 Page: 58, (ClinPharm) 22-23, 41-42, 90	weak [Ki 81.7 uM]
CYP2D6 1891	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=18, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=92 Page: (ClinPharm) 18, 47-49, 89-94	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). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=18, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=92 Page: (ClinPharm) 18, 47-49, 89-94
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=18, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=92 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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=18, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=49, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=92 Page: (ClinPharm) 18, 47-49, 89-94
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022567s021lbl.pdf#page=12 Page: (Label) 12	weak	yes (co-administration study) Comment: Coadministration of Vilazodone slightly increased Digoxin (P-gp substrate) AUC and Cmax (less than 25%). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022567s021lbl.pdf#page=12 Page: (Label) 12

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C8 693	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58 Page: 58.0	likely
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39	likely
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=84 Page: 58, (ClinPharm) 14, 18, 21, 22, 23, 37-39, 82-84	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) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=84 Page: 58, (ClinPharm) 14, 18, 21, 22, 23, 37-39, 82-84
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: 58, (ClinPharm) 18, 22, 37-39	minor
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=58, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: 58, (ClinPharm) 18, 22, 37-39	minor
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39	minor
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39	unlikely
CYP2A6 543	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000ClinPharmR.pdf#page=39 Page: (ClinPharm) 22, 37-39	unlikely

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022567Orig1s000PharmR.pdf#page=48 Page: 48.0

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Relative efficacy and tolerability of vortioxetine versus selected antidepressants by indirect comparisons of similar clinical studies.	2014 Dec	25249164
A review of the clinical efficacy, safety and tolerability of the antidepressants vilazodone, levomilnacipran and vortioxetine.	2014 Dec	25224953
Bioavailability comparison of a new form of vilazodone XVII to IV in beagles using liquid chromatography/mass spectrometry.	2014 Dec	24853720
Efficacy and safety of vilazodone in major depressive disorder: a randomized, double-blind, placebo-controlled trial.	2014 Nov	25470094
Efficacy of vilazodone on anxiety symptoms in patients with major depressive disorder.	2014 Nov	24978955
A validated LC-MS/MS method for the rapid quantification of vilazodone in rat plasma: application to a pharmacokinetic study.	2014 Sep	24937809
Identification of hydrolytic and isomeric N-oxide degradants of vilazodone by on line LC-ESI-MS/MS and APCI-MS.	2015 Jan	25459935
Psychotropic exposures in pediatric patients: Symptomatic iloperidone and vilazodone ingestions.	2015 Mar	25646639
Issues encountered in recent attempts to develop novel antidepressant agents.	2015 May	25762133

Patents

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

Name

Type

Language

VILAZODONE HYDROCHLORIDE

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