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Vilazodone

July 24, 2017
Common Name

Vilazodone Description

Vilazodone is a novel compound with combined high affinity and selectivity for the 5-hydroxytryptamine (5-HT) transporter and 5-HT(1A) receptors. It has been shown to be equally efficacious as other antidepressants with similar gastrointestinal side effects and possibly with reduced sexual side effects and weight gain. Vilazodone is an antidepressant agent that can used as an alternative for patients who cannot tolerate therapy with other antidepressant classes such as selective serotonin reuptake inhibitors or serotonin norepinephrine reuptake inhibitors. Treatment sholid be titrated towards the target dose, which is 40mg per day. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source VilazodonaChEBI VilazodonumChEBI SB 659746aHMDB HCL, VilazodoneMeSH Hydrochloride, vilazodoneMeSH 2-Benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)MeSH ViibrydMeSH Vilazodone HCLMeSH Vilazodone hydrochlorideMeSH 5-(4-(4-(5-cyano-3-Indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamideMeSH

Chemical Formlia

C26H27N5O2 Average Molecliar Weight

441.5249 Monoisotopic Molecliar Weight

441.216475133 IUPAC Name

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

vilazodone CAS Registry Number

163521-12-8 SMILES

NC(=O)C1=CC2=C(O1)C=CC(=C2)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1

InChI Identifier

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)

InChI Key

SGEGOXDYSFKCPT-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Diazinanes Direct Parent

N-arylpiperazines Alternative Parents

  • 3-alkylindoles
  • Benzofurans
  • 2-heteroaryl carboxamides
  • Furoic acid and derivatives
  • Dialkylarylamines
  • N-alkylpiperazines
  • Aralkylamines
  • Substituted pyrroles
  • Benzenoids
  • Heteroaromatic compounds
  • Trialkylamines
  • Primary carboxylic acid amides
  • Amino acids and derivatives
  • Oxacyclic compounds
  • Nitriles
  • Azacyclic compounds
  • Hydrocarbon derivatives
  • Organic oxides
  • Organooxygen compounds
  • Organopnictogen compounds

    • Substituents

  • N-arylpiperazine
  • 3-alkylindole
  • Benzofuran
  • Indole
  • Indole or derivatives
  • 2-heteroaryl carboxamide
  • Furoic acid or derivatives
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aralkylamine
  • N-alkylpiperazine
  • Substituted pyrrole
  • Benzenoid
  • Furan
  • Pyrrole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Primary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • N-arylpiperazine (CHEBI:70707 )
  • monocarboxylic acid amide (CHEBI:70707 )
  • 1-benzofurans (CHEBI:70707 )
  • indoles (CHEBI:70707 )
  • nitrile (CHEBI:70707 )
  • N-alkylpiperazine (CHEBI:70707 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antidepressants
  • Selective Serotonin Reuptake Inhibitors (SSRIs)
  • Serotonin Agonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.23e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.12 mg/mLALOGPS logP4.21ALOGPS logP3.72ChemAxon logS-3.6ALOGPS pKa (Strongest Acidic)14.19ChemAxon pKa (Strongest Basic)8.6ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area102.29 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity129.71 m3·mol-1ChemAxon Polarizability50.02 Å3ChemAxon Number of Rings5ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06684

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06684

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06684 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5293518 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Vilazodone NuGOwiki Link

    HMDB15637 Metagene Link

    HMDB15637 METLIN ID

    Not Available PubChem Compound

    6918314 PDB ID

    Not Available ChEBI ID

    412971

    Product: Hydroxyzine (dihydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [PubMed:12183683 ]
    2. de Paulis T: Drug evaluation: Vilazodone–a combined SSRI and 5-HT1A partial agonist for the treatment of depression. IDrugs. 2007 Mar;10(3):193-201. [PubMed:17351874 ]
    3. Dawson LA, Watson JM: Vilazodone: a 5-HT1A receptor agonist/serotonin transporter inhibitor for the treatment of affective disorders. CNS Neurosci Ther. 2009 Summer;15(2):107-17. [PubMed:19499624 ]
    4. Howland RH: Vilazodone: another novel atypical antidepressant drug. J Psychosoc Nurs Ment Health Serv. 2011 Mar;49(3):19-22. doi: 10.3928/02793695-20110203-98. Epub 2011 Feb 16. [PubMed:21323263 ]
    5. Traynor K: Vilazodone approved for major depression. Am J Health Syst Pharm. 2011 Mar 1;68(5):366. doi: 10.2146/news110009. [PubMed:21330672 ]
    6. Khan A, Cutler AJ, Kajdasz DK, Gallipoli S, Athanasiou M, Robinson DS, Whalen H, Reed CR: A randomized, double-blind, placebo-controlled, 8-week study of vilazodone, a serotonergic agent for the treatment of major depressive disorder. J Clin Psychiatry. 2011 Apr;72(4):441-7. doi: 10.4088/JCP.10m06596. [PubMed:21527122 ]
    7. Dopheide JA: Vilazodones comparative merits yet to be demonstrated. Am J Health Syst Pharm. 2012 Sep 15;69(18):1549. doi: 10.2146/ajhp110570. [PubMed:22935936 ]
    8. Wang SM, Han C, Lee SJ, Patkar AA, Masand PS, Pae CU: A review of current evidence for vilazodone in major depressive disorder. Int J Psychiatry Clin Pract. 2013 Aug;17(3):160-9. doi: 10.3109/13651501.2013.794245. Epub 2013 May 29. [PubMed:23578403 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    General function:
    Involved in monooxygenase activity
    Specific function:
    Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
    Gene Name:
    CYP2D6
    Uniprot ID:
    P10635
    Molecular weight:
    55768.94
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP2C18
    Uniprot ID:
    P33260
    Molecular weight:
    55710.075
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
    Gene Name:
    HTR1A
    Uniprot ID:
    P08908
    Molecular weight:
    46106.3
    References
    1. Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [PubMed:12183683 ]
    2. Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [PubMed:15507223 ]

    Transporters

    General function:
    Involved in neurotransmitter:sodium symporter activity
    Specific function:
    Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
    Gene Name:
    SLC6A4
    Uniprot ID:
    P31645
    Molecular weight:
    70324.165
    References
    1. Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [PubMed:12183683 ]
    2. Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [PubMed:15507223 ]

    PMID: 12205187

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