Vilazodone (CED0007531)

Record Information

Version

1.0

Creation Date

2016-05-25 18:29:32 UTC

Update Date

2026-08-22 06:23:58 UTC

SynCED ID

CED0007531

Secondary Accession Numbers

CHEM022352

Identification

Common Name

Vilazodone

Class

Small Molecule

Description

Vilazodone is an organic compound with the formula C26H27N5O2 and an average molecular weight of 441.52 g/mol. Vilazodone belongs to the piperazines, a subclass of diazinanes within the organic compounds. It is classified as an organoheterocyclic compound. This compound is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as an antidepressant, with a recorded oral exposure route. Vilazodone acts on two recorded protein targets: the sodium-dependent serotonin transporter (SLC6A4) and the 5-hydroxytryptamine receptor 1A (HTR1A), for which it serves as an agonist/inhibitor.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vilazodona	ChEBI
Vilazodonum	ChEBI
SB 659746a	HMDB
HCL, Vilazodone	HMDB
Hydrochloride, vilazodone	HMDB
2-Benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)	HMDB
Viibryd	HMDB
Vilazodone HCL	HMDB
Vilazodone hydrochloride	HMDB
5-(4-(4-(5-Cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamide	HMDB

Chemical Formula

C₂₆H₂₇N₅O₂

Average Molecular Mass

441.525 g/mol

Monoisotopic Mass

441.216 g/mol

CAS Registry Number

163521-12-8

IUPAC Name

5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide

Traditional Name

vilazodone

SMILES

NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1

InChI Identifier

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)

InChI Key

SGEGOXDYSFKCPT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

N-arylpiperazines

Alternative Parents

Substituents

N-arylpiperazine
3-alkylindole
Benzofuran
Indole
Indole or derivatives
2-heteroaryl carboxamide
Furoic acid or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aralkylamine
N-alkylpiperazine
Substituted pyrrole
Benzenoid
Furan
Pyrrole
Heteroaromatic compound
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Nitrile
Carbonitrile
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:70707 )
monocarboxylic acid amide (CHEBI:70707 )
1-benzofurans (CHEBI:70707 )
indoles (CHEBI:70707 )
nitrile (CHEBI:70707 )
N-alkylpiperazine (CHEBI:70707 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

agonist (PMC11152992 )?
Antidepressant (PMC11152992 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	4.21	ALOGPS
logP	3.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.19	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.71 m³·mol⁻¹	ChemAxon
Polarizability	50.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0pb9-1892200000-e80db0623de8c5d5253b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-0100900000-419df74d78f3394907e4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-0211900000-fc5409d02ddc3a074e29	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ard-0930000000-ca1734ab642c796bbcaf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0000900000-709b81c1b5cb6d2d8c1b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0005-1009600000-913d3342fc1dba5181ae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9341100000-d9863664c2546f78ac6b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0000900000-fb0afc1a6de498c1d581	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002g-0201900000-7049e2907cdc39ce7fa8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pba-0931100000-c3a86c8646e2eb2feac2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0004900000-f0610bc45efeb8e8cd19	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-5006900000-70aadc301ad860239f5b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-5598400000-9ca429b67adcdbb9ca8b	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
489.0 Log mg/kg [280:870]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
Alzheimer's disease	Not Available	Not Available	A neurodegenerative disease which causes neural atrophy, leading to dementia and memory loss.	PMC13144357
depressive disorder	Not Available	Not Available	Not Available	PMC13144357

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000377	Antidepressants?Antidepressants, a class of synthetic chemicals designed to alleviate symptoms of depression and anxiety, can enter the environment through various pathways, leading to contamination of water systems.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000476	Biosolids?Biosolids are nutrient-rich organic materials derived from the treatment of sewage sludge during wastewater management processes.	Wastewater, sanitation & biosolids	PMC13003354
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs03009	Waste Water	Wastewater, sanitation & biosolids	PMC10321226

Pathways

3 pathwaysPathway Source: PathBank

Vilazodone mechanism of Action Action Pathway

Vilazodone Drug Metabolism Action Pathway

Vilazodone Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.734 Applicability Domain 1.0 Statistical Significance 1.80e-04 Supporting Reference Compounds 953 E-value 1.40129
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.713 Applicability Domain 1.0 Statistical Significance 9.00e-05 Supporting Reference Compounds 593 E-value 0.700643
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.677 Applicability Domain 1.0 Statistical Significance 1.10e-04 Supporting Reference Compounds 451 E-value 0.856341
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	Prediction Confidence Score 0.674 Applicability Domain 1.0 Statistical Significance 2.60e-04 Supporting Reference Compounds 506 E-value 2.02408
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.631 Applicability Domain 1.0 Statistical Significance 9.20e-04 Supporting Reference Compounds 541 E-value 7.16213
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.612 Applicability Domain 1.0 Statistical Significance 5.60e-04 Supporting Reference Compounds 565 E-value 4.35956
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.61 Applicability Domain 1.0 Statistical Significance 6.80e-04 Supporting Reference Compounds 297 E-value 5.29375
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.609 Applicability Domain 1.0 Statistical Significance 0.0023 Supporting Reference Compounds 1103 E-value 17.9053
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.597 Applicability Domain 1.0 Statistical Significance 0.0018 Supporting Reference Compounds 528 E-value 13.935
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.533 Applicability Domain 1.0 Statistical Significance 0.0037 Supporting Reference Compounds 1498 E-value 29.1935
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.506 Applicability Domain 0.984 Statistical Significance 0.0048 Supporting Reference Compounds 861 E-value 37.0562
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.479 Applicability Domain 0.984 Statistical Significance 0.0027 Supporting Reference Compounds 536 E-value 21.175
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.477 Applicability Domain 0.984 Statistical Significance 0.0018 Supporting Reference Compounds 365 E-value 14.1686
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	Prediction Confidence Score 0.477 Applicability Domain 0.984 Statistical Significance 0.0017 Supporting Reference Compounds 337 E-value 13.3122
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	Prediction Confidence Score 0.471 Applicability Domain 0.984 Statistical Significance 0.0047 Supporting Reference Compounds 524 E-value 36.9784
Click to view 3D structure	Acetylcholinesterase	P21836	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.466 Applicability Domain 0.56 Statistical Significance 0.001 Supporting Reference Compounds 58 E-value 7.94062
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.449 Applicability Domain 1.0 Statistical Significance 0.0044 Supporting Reference Compounds 380 E-value 34.4094
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	Prediction Confidence Score 0.448 Applicability Domain 0.984 Statistical Significance 0.0044 Supporting Reference Compounds 507 E-value 34.0201
Click to view 3D structure	5-hydroxytryptamine receptor 7	P32305	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.445 Applicability Domain 1.0 Statistical Significance 0.0028 Supporting Reference Compounds 115 E-value 21.7199
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.441 Applicability Domain 0.984 Statistical Significance 0.0049 Supporting Reference Compounds 686 E-value 37.8347
Click to view 3D structure	D(4) dopamine receptor	P30729	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.438 Applicability Domain 1.0 Statistical Significance 0.0011 Supporting Reference Compounds 92 E-value 8.95266
Click to view 3D structure	Butyrylcholinesterase	Q9JKC1	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.438 Applicability Domain 0.573 Statistical Significance 0.0014 Supporting Reference Compounds 32 E-value 11.2881
Click to view 3D structure	D(3) dopamine receptor	P19020	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.438 Applicability Domain 1.0 Statistical Significance 0.0036 Supporting Reference Compounds 145 E-value 28.415
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.43 Applicability Domain 0.984 Statistical Significance 0.0073 Supporting Reference Compounds 562 E-value 56.6742
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.43 Applicability Domain 1.0 Statistical Significance 0.002 Supporting Reference Compounds 154 E-value 15.5698