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VILAZODONE

VILAZODONE structure

CAS No:
163521-12-8
Formula:
C26H27N5O2
Chemical Name:
VILAZODONE
Synonyms:
2-BenzofurancarboxaMide,5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-;Vilazodonei;Vilazodone 5-[4-[4-(5-Cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide;5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide;Verazodone hydrochloride;VIIBRYD; 5-(4-[4-(5-CYANO-1H-INDOL-3-YL)BUTYL]PIPERAZIN-1-YL)BENZOFURAN-2-CARBOXAMIDE;CS-108;5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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.

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.

Light Yellow Solid

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.

VILAZODONE Basic Attributes

Molecular Weight：

441.52

Exact Mass：

441.52

EC Number：

1308068-626-2

Color/Form：

Pale Yellow to Beige

Characteristics

Density：

1.34±0.1 g/cm3(Predicted)

Melting Point：

203-205°C

Boiling Point：

745.1±60.0 °C(Predicted)

PKA：

15.98±0.30(Predicted)

Critical Temperature & Pressure：

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

VILAZODONE Use and Manufacturing

Labelled analogue of Vilazodone

An inhibitor of ST and activator of SR-1A

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.

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