Guidechem | China Chemical Manufacturers,suppliers,B2B Marketplace
Encyclop..
  • Products
  • Encyclopedia
  • Buy offers
  • Suppliers
Home> Encyclopedia >   /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Custom Manufacturing
VILAZODONE structure
VILAZODONE structure

VILAZODONE

Iupac Name:5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide
CAS No.: 163521-12-8
Molecular Weight:477.993
Modify Date.: 2022-10-31 05:05
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
VILAZODONE
1.2 Synonyms

2-Benzofurancarboxamide, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]- 2-BenzofurancarboxaMide,5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]- 5-(4-(4-(5-Cyano-1H-indol-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 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide 5-{4-[4-(5-Cyano-1H-indol-3-yl)butyl]-1-piperazinyl}-1-benzofuran-2-carboxamide 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide CS-108 Verazodone hydrochloride VIIBRYD Vilazodone 5-[4-[4-(5-Cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide Vilazodonei

1.3 CAS No.
163521-12-8
1.4 CID
6918314
1.5 EINECS(EC#)
1308068-626-2
1.6 Molecular Formula
C26H27N5O2 (isomer)
1.7 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)
1.8 InChkey
SGEGOXDYSFKCPT-UHFFFAOYSA-N
1.9 Canonical Smiles
C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N
1.10 Isomers Smiles
C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N
2. Properties
2.1 Density
1.34
2.1 Melting point
203-205 °C
2.1 Boiling point
745.1 °C at 760 mmHg
2.1 Flash Point
745.1 °C at 760 mmHg
2.1 Precise Quality
477.19300
2.1 PSA
102.29000
2.1 logP
5.53478
2.1 Solubility
In water, 6.125X10-2 mg/L at 25 °C (est)
2.2 Appearance
Light yellow solid
2.3 Chemical Properties
Light Yellow Solid
2.4 Decomposition
May emit toxic gasses like Carbon monoxide, Carbon dioxide, Nitrogen oxides upon thermal decomposition. /Vilazodone hydrochloride/
2.5 pKa
15.98±0.30(Predicted)
2.6 Water Solubility
In water, 6.125X10-2 mg/L at 25 °C (est)
2.7 Stability
Stable under normal handling conditions. /Vilazodone hydrochloride/
2.8 StorageTemp
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
3. Use and Manufacturing
3.1 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.
3.2 Usage
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.
4. Safety and Handling
4.1 Specification

The cas register number of Vilazodone is 163521-12-8. It also can be called as 2-benzofurancarboxamide, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]- and the Systematic name about this chemical is 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide.

Physical properties about Vilazodone are: (1)ACD/LogP: 3.99 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 2.26 ; (4)ACD/LogD (pH 7.4): 3.76 ; (5)ACD/BCF (pH 5.5): 11.76; (6)ACD/BCF (pH 7.4): 371.61; (7)ACD/KOC (pH 5.5): 65.58; (8)ACD/KOC (pH 7.4): 2071.96; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 68.65Å2; (13)Index of Refraction: 1.711; (14)Molar Refractivity: 128.68 cm3; (15)Molar Volume: 328.7 cm3; (16)Surface Tension: 75.2 dyne/cm; (17)Density: 1.34 g/cm3; (18)Flash Point: 404.4 °C; (19)Enthalpy of Vaporization: 108.63 kJ/mol; (20)Boiling Point: 745.1 °C at 760 mmHg; (21)Vapour Pressure: 4.5E-22 mmHg at 25°C.

People can use the following data to convert to the molecule structure.
1.SMILES: N#Cc1ccc2c(c1)c(cn2)CCCCN5CCN(c4cc3c(oc(c3)C(=O)N)cc4)CC5
2.InChI: InChI=1/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) 
3.InChIKey: SGEGOXDYSFKCPT-UHFFFAOYAC
4.Std. 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).

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

6. Synthesis Route
8. Other Information
8.0 References
https://www.drugbank.ca/drugs/DB06684
https://en.wikipedia.org/wiki/Vilazodone
http://www.rxlist.com/viibryd-drug/indications-dosage.htm
8.1 Chemical Properties
Light Yellow Solid
8.2 Uses
Labelled analogue of Vilazodone
8.3 Uses
An inhibitor of ST and activator of SR-1A
8.4 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.
8.5 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.
8.6 体外研究

Vilazodone shows an IC 50 of 0.2 nM at the human 5-HT 1 A receptor and 0.5 nM for the SERT. Vilazodone preferentially binds to the high agonist affinity state of human 5-HT 1 A receptors, and it displays high affinity (pK i ≥9.3) for human recombinant and rat, guinea pig, mouse, and marmoset native tissue 5-HT 1A receptors.Vilazodone acts as a high efficacy partial agonist at 5-HT 1 A receptors. In [ 35 S]GTPγS binding studies in Sf9 cells expressing h5-HT 1 A receptors, a single concentration of Vilazodone (100nM) increases basal binding by approximately 70% of that produced by the full 5-HT 1 A receptor agonist, 8‐OH‐PIPAT. In [ 35 S]GTPγS binding studies in rat hippocampal membranes, Vilazodone acts as a potent 5‐HT 1A receptor partial agonist with a pEC 50 of 8.1 and an intrinsic activity of 0.61. Vilazodone acts as a potent 5‐HT reuptake inhibitor in rat and guinea pig cortex. In LLCPK cells expressing human SERT, whereby vilazodone inhibits [ 3 H]5‐HT uptake with a pIC 50 of 8.8.

8.7 体内研究

Vilazodone (intraperitoneal injection; 3 mg/kg ; single dose) produces increases in extracellular levels of 5‐HT in both the frontal cortex (FC) and ventral hippocampus (vHipp) of rats in vivo microdialysis studies. Maximum increases are observed at 3 mg/kg and reaches 527% and 558% of preinjection baseline values in the FC and vHipp, respectively. Vilazodone (oral gavage ;55 mg/kg ; single dose) inhibits stress‐induced vocalizations in the rat ultrasonic vocalizations test at 120 and 210 min post dose.

8.8 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.
8.9 Originator
Merck KGaA (Germany)
8.10 Brand name
Viibryd
9. Computational chemical data
  • Molecular Weight: 477.993g/mol
  • Molecular Formula: C26H27N5O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 4
  • Exact Mass: 441.21647512
  • Monoisotopic Mass: 441.21647512
  • Complexity: 729
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Topological Polar Surface Area: 102
  • Heavy Atom Count: 33
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB7sAAAAAAAAAAAAAAAAAAAAWJAAAA8YIAAAAAAAFgB/gAAHgAQAAAADAzBngQ8xvPJlEC4B7V3VAKiiCA1IiAI2aH+bNgO5vLEtZ+XOSjk0BHI6Y+83+P+iEACQAAKAAAQgASAABQAAAAAAAAAAA==
10. Recommended Suppliers
Global130SuppliersView all >>
  • Products:xylazine hcl,phenacetin,4-Methylpropiophenone,(2-Bromoethyl)benzene,4-Methoxybenzoyl chloride
  • Tel:86-311-17798046959
  • Email:ellie@hbyingong.com
China Factory Direct Sale CAS 163521-12-8 Vilazodone Purity >99%
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 220 USD/kg
  • Time: 2022/12/03
Inquire
  • Products:pharmaceutical intermediates Organic raw materialsAnimal and plant extracts1.4BDO, Eutylone,4MMC, JWH ,SGT Peptide, Steroids, Benzos,Dissociatives
  • Tel:86-311-19832408762
  • Email:salesperson66@yeah.net
Vilazodone CAS 163521-12-8
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 10 USD/g
  • Time: 2022/12/02
Inquire
  • Products:biotechnology pharmaceutical intermediates biotechnology medical intermediates
  • Tel:0086-0310-15343106358
  • Email:guide@cnyouze.com
Manufacturer of Vilazodone (EMD 68843; SB 659746A) at Factory Price CAS NO.163521-12-8
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 8 USD/kg
  • Time: 2022/11/25
Inquire
  • Products:Cangzhou Enke Pharma-tech Co.,Ltd (China) is a leading manufacturer of innovative chemistry products and services throughout the pharmaceutical R&D process and commercial production.
  • Tel:0086-317-5296180
  • Email:sale@enkepharma.com
Vilazodone
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 111 USD/kilogram
  • Time: 2022/08/11
Inquire
  • Products:Pharmaceutical raw materials,Chemical reagent, Food aditives,Plant ExtracPharmaceutical and pesticide intermediates.
  • Tel:86-431-81915458
  • Email:cathytan@jltely.com
CAS No.: 163521-12-8 2-Benzofurancarboxamide,5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kilogram
  • Time: 2022/12/02
Inquire
11. Realated Product Infomation