Vilazodone

Base Information

• Chemical Name: Vilazodone
• CAS No.: 163521-12-8
• Molecular Formula: C26H27N5O2
• Molecular Weight: 441.533
• UNII: S239O2OOV3
• DSSTox Substance ID: DTXSID80870086
• Nikkaji Number: J829.149G
• Wikipedia: Vilazodone
• Wikidata: Q408588
• NCI Thesaurus Code: C90716
• RXCUI: 1086769
• Pharos Ligand ID: YCR64UZMTFBN
• Metabolomics Workbench ID: 43672
• ChEMBL ID: CHEMBL439849
• Mol file: 163521-12-8.mol

Synonyms:2-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1);5-(4-(4-(5-cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamide;68843, EMD;EMB 68843;EMB-68843;EMB68843;EMD 68843;HCl, Vilazodone;Hydrochloride, Vilazodone;Viibryd;vilazodone;Vilazodone HCl;vilazodone hydrochloride

Chemical Property of Vilazodone

Chemical Property:

• Appearance/Colour: Light yellow solid
• Melting Point: 203-205 °C
• Boiling Point: 745.076 °C at 760 mmHg
• PKA: 15.98±0.30(Predicted)
• Flash Point: 404.408 °C
• PSA: 102.29000
• Density: 1.343 g/cm³
• LogP: 5.53478
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly)), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 441.21647512
• Heavy Atom Count: 33
• Complexity: 729

Purity/Quality:

98% up, ^*data from raw suppliers

Vilazodone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N
• Recent ClinicalTrials: Double-Blind Treatment of Major Depressive Disorder With Vilazodone
• Recent EU Clinical Trials: A Multicenter, Randomized, Double-Blind, Placebo-Controlled, Relapse Prevention Study with Vilazodone in Patients with Major Depressive Disorder
• 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.
• 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. Labelled analogue of Vilazodone An inhibitor of ST and activator of SR-1A

Technology Process of Vilazodone

There total 113 articles about Vilazodone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

methyl 5-{4-[4-(5-cyano-1H-indol-3-yl)-butyl]-piperazin-1-yl}-benzofuran-2-carboxylate (1236722-93-2) → vilazodone (163521-12-8)

Guidance literature:

With ammonia; In methanol; at 25 - 30 ℃; Concentration; Pressure; Time;

Reference yield: 95.7%

3-(4-chlorobutyl)-5-cyanoindole (143612-79-7) + 5-(1-piperazinyl)benzofuran-2-carboxamide (183288-46-2) → vilazodone (163521-12-8)

Guidance literature:

3-(4-chlorobutyl)-5-cyanoindole; With sodium iodide; In N,N-dimethyl-formamide; at 25 - 30 ℃; for 0.25h;

5-(1-piperazinyl)benzofuran-2-carboxamide; With tetrabutylammomium bromide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 110 - 115 ℃; for 1.25h; Reagent/catalyst; Temperature; Time; Solvent;

Reference yield: 93.0%

5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxylic acid ethyl ester hydrochloride (1422956-25-9,163521-09-3) → vilazodone (163521-12-8)

Guidance literature:

With ammonium hydroxide; In methanol; at 50 ℃; for 22h; Reagent/catalyst; Time; Temperature; Autoclave;

upstream raw materials:

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

1H-indole-5-carbonitrile

ethyl 5-nitrobenzo[d]furan-2-carboxylate

ethyl 5-amino-1-benzofuran-2-carboxylate

Downstream raw materials:

1-(2-carbamoylbenzofuran-5-yl)-4-(4-(5-cyano-1H-indol-3-yl)butyl)piperazine 4-oxide

Refernces

• 1、 Hu, Fan,Su, Weike. "An investigation of the synthesis of vilazodone". . p. 243 - 247. Retrieved 2020/01/08.
• 2、 -. "Preparation method of vilazodone or hydrochloride thereof". Paragraph 0044; 0045. . Retrieved 2018/09/14.