Vilazodone HCl (EMD 68843; SB659746A)

Alias: EMD68843; SB659746A; SB659746-A;EMD-68843; EMD68843; SB659746 A; Vilazodone hydrochloride; Viibryd

Cat No.:V0972 Purity: ≥98%

COA Product Data Instructions for use SDS

Vilazodone HCl (EMD 68843; SB659746A) Chemical Structure CAS No.: 163521-08-2
Product category: 5-HT Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Vilazodone HCl (EMD 68843; SB659746A):

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

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Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

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Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Vilazodone HCl (SB659746A; SB659746-A; EMD-68843; EMD68843; Viibryd), the hydrochloride salt of Vilazodone, is a selective serotonin reuptake inhibitor (SSRI) and a partial agonist of 5-HT1A receptors with anti-depressive effects. Vilazodone was given FDA approval in 2011 to treat major depressive disorders. Vilazodone's half-life at the human 5-HT1A receptor is 0.2 nM, while its half-life for the SERT is 0.5 nM. Vilazodone binds to native tissue 5-HT1A receptors in rats, mice, marmosets, and guinea pigs with high affinity (pKi ≥ 9.3), as well as human recombinant receptors.

Biological Activity I Assay Protocols (From Reference)

Targets

sPLA2; 5-HT_1A Receptor

ln Vitro

In vitro activity: Vilazodone exhibits an IC50 of 0.5 nM for the SERT and 0.2 nM at the human 5-HT1A receptor. Vilazodone exhibits a high affinity (pKi ≥ 9.3) for native tissue 5-HT1A receptors found in rats, mice, guinea pigs, and marmosets, as well as human recombinant receptors.[1]

ln Vivo

Vilazodone increases serotonergic output in the rat prefrontal cortex in a selective manner. Vilazodone's anxiolytic effectiveness is demonstrated by behavioral assessments in the ultrasonic vocalization model of anxiety in rats. Vilazodone is also effective, but only when taken as a single dose in the forced swim test, which is used as a potential model of depression.[1] In vivo [3H]DASB (N,N-dimethyl-2-(2-amino-4-cyanophenylthio)benzylamine) binding is dose-dependently displaced by vilazodone (1–10 mg/kg p.o.) from rat cortex and hippocampus, suggesting that vilazodone occupies 5-HT transporters. In the frontal cortex of freely moving rats, vilazodone (10 mg/kg p.o.) is shown to cause a 2-fold increase in extracellular 5-HT but no change in noradrenaline or dopamine levels.[2] Vilazodone has an impact on rats' stress potentiation of startle at doses greater than 5 mg/kg. In rats, vilazodone elevates startle stress at a dose of 10 mg/kg. In rats, vilazodone (20 and 40 mg/kg) inhibited the stress-induced potentiation of startle. In rats, vilazodone elevates startle in response to stress at all doses.[3] In the guinea-pig dorsal raphe nucleus, vilazodone dramatically reduces 5-HT efflux at 1 mM but has no effect on it at 100 nM. Vilazodone prolongs the half-life of 5-HT reuptake in the guinea-pig dorsal raphe nucleus by a significant amount.[4]

Cell Assay

Administration of 5-HT1A receptor agonists results in a distinct behavioral syndrome that includes head weaving, tremors, forepaw treading, posture abnormalities, hind limb reduction, and straub tail. At 120 and 210 minutes after dosing, Vilazodone (55 mg/kg po) inhibits stress-induced vocalizations in the rat ultrasonic vocalization exercise. Vilazodone (20–40 mg/kg ip) inhibited stress-induced potentiated startle but had no effect on stress-potentiated anxiety response in the elevated plus maze when given acutely or preventatively one week before behavioral testing. The startle response is interestingly affected in the opposite way by a lower dose of 10 mg/kg of vilazodone, suggesting a bidirectional effect that is not fully understood. Additionally, all doses of the drug increase the startle-induced stress response, which may be indicative of an anxiogenic-like reaction. Vilazodone is an additional treatment option for Major Depressive Disorder.

Animal Protocol

1-10 mg/kg; p.o.

Rats

References

[1]. CNS Neurosci Ther . 2009 Summer;15(2):107-17.

[2]. Eur J Pharmacol . 2005 Mar 7;510(1-2):49-57.

[3]. Eur J Pharmacol . 2004 Nov 3;504(1-2):65-77.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C26H28CLN5O2

Molecular Weight

477.99

Exact Mass

477.19

Elemental Analysis

C, 65.33; H, 5.90; Cl, 7.42; N, 14.65; O, 6.69

CAS #

163521-08-2

Related CAS #

Vilazodone-d8; 1794789-93-7; Vilazodone; 163521-12-8; Vilazodone carboxylic acid; 163521-19-5

Appearance

Solid powder

SMILES

C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N.Cl

InChi Key

RPZBRGFNBNQSOP-UHFFFAOYSA-N

InChi Code

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

Chemical Name

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

Synonyms

EMD68843; SB659746A; SB659746-A;EMD-68843; EMD68843; SB659746 A; Vilazodone hydrochloride; Viibryd

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 25~96 mg/mL (52.3~200.8 mM)

Water: <1 mg/mL

Ethanol: <1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.0921 mL	10.4605 mL	20.9209 mL
	5 mM	0.4184 mL	2.0921 mL	4.1842 mL
	10 mM	0.2092 mL	1.0460 mL	2.0921 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

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Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT05948579	Not yet recruiting	Drug: Intervention B Vilazodone Hydrochloride (HCl) Drug: Intervention B Placebo	Post Traumatic Stress Disorder	U.S. Army Medical Research and Development Command	August 2023	Phase 2
NCT05422612	Recruiting	Drug: Intervention A Placebo Drug: Intervention B Placebo	Post Traumatic Stress Disorder	U.S. Army Medical Research and Development Command	November 2, 2023	Phase 2
NCT02015546	Completed	Drug: Vilazodone	Major Depressive Disorder (MDD)	Duke University	December 2012	Phase 3
NCT02436239	Completed	Drug: Vilazodone	Major Depressive Disorder	Forest Laboratories	May 2, 2015	Phase 3
NCT01828515	Completed	Drug: Vilazodone Drug: Placebo	Memory Impairment	University of Texas Southwestern Medical Center	December 2012	Phase 2

Biological Data

Chemical structure of vilazodone and its primary metabolite. CNS Neurosci Ther . 2009 Summer;15(2):107-17.
Inhibition of [³H]5‐HT uptake into LLCPK cells expressing human recombinant SERT by vilazodone. Methodology as described by Scott et al. CNS Neurosci Ther . 2009 Summer;15(2):107-17.