VILAZODONE Chemical Properties

Melting point:

203-205°C

Boiling point:

745.1±60.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly)), Methanol (Slightly)

pka

15.98±0.30(Predicted)

form 

Solid

color 

Pale Yellow to Beige

Stability:

Very Hygroscopic

InChI

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)

InChIKey

SGEGOXDYSFKCPT-UHFFFAOYSA-N

SMILES

O1C2=CC=C(N3CCN(CCCCC4C5=C(NC=4)C=CC(C#N)=C5)CC3)C=C2C=C1C(N)=O

CAS DataBase Reference

163521-12-8

Safety Information

Hazardous Substances Data

163521-12-8(Hazardous Substances Data)

VILAZODONE Usage And Synthesis

Description

Vilazodone is a kind of serotonergic antidepressant developed by Merck KGaA Company. It is a novel compound with high affinity and selectivity for the 5-hydroxytrptamine (5-HT) transporter and 5-HT (1A) receptors. It is indicated for the treatment of major depressive disorder (MDD). It is can be used as an alternative drugs for other kind of antidepressant classes drugs that can’t be tolerated by patients. As a selective serotonin reuptake inhibitor, vilazodone can prevent the serotonin from re-entering into cell bodies, therefore making it remain longer inside the synapse. Moreover, it has a high selectivity for the serotonin-1A receptor, taking effect as a partial agonist that can simulate the production of serotonin. These effects result in increased serotonin in the synaptic cleft. This effect is related to the antidepressant effect of vilazodone in vivo.

References

https://www.drugbank.ca/drugs/DB06684
https://en.wikipedia.org/wiki/Vilazodone
http://www.rxlist.com/viibryd-drug/indications-dosage.htm

Description

In January 2011, the U.S. FDA approved vilazodone for the treatment of major depressive disorder (MDD). Vilazodone is a novel antidepressant agent that combines potent serotonin reuptake inhibition (IC₅₀=0.2 nM) with high affinity for 5-HT1A receptors (IC₅₀=0.5 nM)and partial 5-HT1A receptor agonist functional activity. Vilazodone has good selectivity over other monoamine receptors and is efficacious in preclinical models of depression in rats and mice. Vilazodone is an indolylbutylpiperazine derivative that has been prepared by coupling of an indolylbutyl chloride or tosylate with 5-(piperazin-1-yl)benzofuran-2- carboxamide or the corresponding ester. The cyanoindole portion of vilazodone is important for conferring high affinity for both the serotonin transporter and the 5-HT1A receptor. Para-substitution on the phenyl group attached to the piperidine moiety reduces affinity for dopamine receptors, while the carboxamide group provides improved pharmacokinetic properties.

Chemical Properties

Light Yellow Solid

Originator

Merck KGaA (Germany)

Uses

It is a combined serotonin specific reuptake inhibitor (SSRI) and 5-HT1A receptor partial agonist currently under clinical evaluation for the treatment of major depression.

Uses

Labelled analogue of Vilazodone

Uses

An inhibitor of ST and activator of SR-1A

Definition

ChEBI: A 1-benzofuran that is 5-(piperazin-1-yl}-1-benzofuran-2-carboxamide having a (5-cyanoindol-3-yl)butyl group attached at position N-4 on the piperazine ring. Used for the treatment of major depressive disorder.

brand name

Viibryd

Mechanism of action

The mechanism of action of Vilazodone antidepressant is to enhance the release of serotonin from the serotonergic pathway in the brain by inhibiting the serotonin transporter (similar to a selective serotonin reuptake inhibitor (SSRI)) while stimulating the serotonin-1a receptor through partial agonism. Its agonistic effects are similar to those of the anxiolytic drug buspirone.

Side effects

The most common side effects of Vilazodone administered orally include: diarrhoea, dizziness, headache, dry mouth, nausea, vomiting, and sleep disturbances. These symptoms are mild and may disappear within a few days or weeks. Other serious side effects that may occur include: bleeding, hyponatraemia (low levels of sodium in the blood, manifested by dizziness, light-headedness, difficulty concentrating and fainting), mania, seizures (loss of consciousness, twitching of limbs), closed-angle glaucoma (sudden eye pain or loss of vision) and allergic reactions. Seek medical attention if any of these serious adverse symptoms occur.

VILAZODONE(163521-12-8)Related Product Information

• 1-BENZOFURAN-5-AMINE
• Vilazodone Intermediate
• Paliperidone
• Linagliptin
• Anidulafungin
• Bexarotene
• 8-AZAGUANINE
• Silodosin
• Vilazodone impurity 1
• 1H-Indole-5-carbonitrile, 3-(4-hydroxybutyl)-
• 3-(4-Chloro-1-hydroxybutyl)-1H-indole-5-carbonitrile
• ISO-PROPYLCHLOROBUTYRATE
• 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid
• Vilazodone Hydrochloride
• Vilazodone Impurity 24
• Verazolonone related impurities
• Vilazodone Impurity 5
• Vilazodone Impurity 30