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

• ChemBase ID: 130145
• Molecular Formular: C26H27N5O2
• Molecular Mass: 441.52488
• Monoisotopic Mass: 441.21647513
• SMILES: N#Cc1ccc2c(c1)c(c[nH]2)CCCCN1CCN(c2cc3c(oc(c3)C(=O)N)cc2)CC1
• Canonical SMILES: N#Cc1ccc2c(c1)c(CCCCN1CCN(CC1)c1ccc3c(c1)cc(o3)C(=O)N)c[nH]2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide
• IUPAC Traditional name: vilazodone
• Brand Name: Viibryd
• Synonyms: 5-[4-[4-(5-Cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxamide; EMD 515259; Vilazodone

Database IDs

• CAS Number: 163521-12-8
• PubChem SID: 162224429
• PubChem CID: 6918313; 6918314
• CHEBI ID: 70707
• ATC CODE: N06AX24
• CHEMBL: 439849
• Chemspider ID: 5293518
• KEGG ID: D09698
• Unique Ingredient Identifier: S239O2OOV3
• Wikipedia Title: Vilazodone
• Medline Plus: a611020

CALCULATED PROPERTIES

• Acid pKa: 14.192648
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7569492
• LogD (pH = 7.4): 2.4867616
• Log P: 3.715304
• Molar Refractivity: 129.7114 cm^3
• Polarizability: 50.78926 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Light Yellow Solid
• Melting Point: 203-205°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 20-24 hours
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)
• US Licence: Vilazodone

DETAILS

Toronto Research Chemicals - V265000

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. Antidepressant.

REFERENCES

• Bartoszyk, G., et al.: Eur. J. Pharmacol., 322, 147 (19970, Heinrich, T., et al.: J. Med. Chem., 47, 4684 (2004)