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    Vilazodone Hydrochloride

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    2D Structure
    Also known as: 163521-08-2, Vilazodone hcl, Viibryd, Vilazodone (hydrochloride), Emd-68843, Emd 68 843
    Molecular Formula
    C26H28ClN5O2
    Molecular Weight
    478.0  g/mol
    InChI Key
    RPZBRGFNBNQSOP-UHFFFAOYSA-N
    FDA UNII
    U8HTX2GK8J
    A benzofuran, indole, and piperazine derivative that functions as a SEROTONIN UPTAKE INHIBITOR and partial SEROTONIN 5-HT1 RECEPTOR AGONIST. It is used as an ANTIDEPRESSIVE AGENT.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C26H27N5O2.ClH/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);1H
    2.1.3 InChI Key
    RPZBRGFNBNQSOP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    U8HTX2GK8J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-benzofurancarboxamide, 5-(4-(4-(5-cyano-1h-indol-3-yl)butyl)-1-piperazinyl)-, Hydrochloride (1:1)

    2. 5-(4-(4-(5-cyano-3-indolyl)butyl)-1-piperazinyl)benzofuran-2-carboxamide

    3. 68843, Emd

    4. Emb 68843

    5. Emb-68843

    6. Emb68843

    7. Emd 68843

    8. Hcl, Vilazodone

    9. Hydrochloride, Vilazodone

    10. Viibryd

    11. Vilazodone

    12. Vilazodone Hcl

    2.3.2 Depositor-Supplied Synonyms

    1. 163521-08-2

    2. Vilazodone Hcl

    3. Viibryd

    4. Vilazodone (hydrochloride)

    5. Emd-68843

    6. Emd 68 843

    7. Vilazodone Hydrochloride [usan]

    8. 5-(4-(4-(5-cyano-1h-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide Hydrochloride

    9. Emd 68843

    10. U8htx2gk8j

    11. Sb659746-a

    12. 163521-08-2 (hcl)

    13. Chebi:70705

    14. Sb659746a

    15. 5-[4-[4-(5-cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide Hydrochloride

    16. Sb 659746a

    17. Sb-659746a

    18. Sb-659746-a

    19. Vilazodone Hydrochloride (usan)

    20. 5-(4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl)benzofuran-2-carboxamide, Hydrochloride

    21. 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide Hydrochloride

    22. 2-benzofurancarboxamide, 5-(4-(4-(5-cyano-1h-indol-3-yl)butyl)-1-piperazinyl)-, Hydrochloride (1:1)

    23. 5-(4-(4-(5-cyano-1h-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide Monohydrochloride

    24. 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide;hydrochloride

    25. 5-{4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide Hydrochloride

    26. Unii-u8htx2gk8j

    27. Vilazodonei

    28. 2-benzofurancarboxamide, 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]-1-piperazinyl]-, Hydrochloride (1:1)

    29. Viibryd (tn)

    30. Vilazodonehydrochloride

    31. Vilazodone Monohydrochloride

    32. Schembl867358

    33. Chembl1615374

    34. Dtxsid80936833

    35. Bcp11496

    36. Emd68843

    37. Mfcd00940014

    38. S4259

    39. Vilazodone Hydrochloride [mi]

    40. Akos024464039

    41. Ccg-213313

    42. Cs-0549

    43. Vilazodone Hydrochloride [mart.]

    44. Vilazodone Hydrochloride [vandf]

    45. Vilazodone Hydrochloride [who-dd]

    46. 5-{4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboximidic Acid--hydrogen Chloride (1/1)

    47. Ac-25885

    48. As-74699

    49. Emd 68843;sb659746a

    50. Hy-14261

    51. Vilazodone Hydrochloride, >=98% (hplc)

    52. A3919

    53. Sw219887-1

    54. V0149

    55. Vilazodone Hydrochloride [orange Book]

    56. D09699

    57. 521v128

    58. J-525160

    59. Q27139037

    60. 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine Hydrochloride

    61. 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)piperazine Hydrochloride

    62. 1-[4-(5-cyanoindol-3-yl)butyl]4-(2-carbamoyl-benzofuran-5-yl)-piperazine Hydrochloride

    63. 5-(4-[4-(5-cyano-3-indolyl)-butyl]-1-piperazinyl)-benzofuran-2carboxamide Hydrochloride

    64. 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxamide Hydrochloride

    65. 4-(2-carbamoyl-1-benzofuran-5-yl)-1-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-ium Chloride

    66. Vilazodone Hydrochloride Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 478.0 g/mol
    Molecular Formula C26H28ClN5O2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass477.1931528 g/mol
    Monoisotopic Mass477.1931528 g/mol
    Topological Polar Surface Area102 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity729
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameViibryd
    PubMed HealthVilazodone (By mouth)
    Drug ClassesAntidepressant
    Drug LabelVIIBRYD Tablets for oral administration contain polymorph Form IV vilazodone hydrochloride (HCl), a selective serotonin reuptake inhibitor and a 5HT1A receptor partial agonist.Vilazodone HCl is 2-benzofurancarboxamide, 5-[4-[4-(5-cyano-1H-indol-3-yl)...
    Active IngredientVilazodone hydrochloride
    Dosage FormTablet
    RouteOral
    Strength10mg; 40mg; 20mg
    Market StatusPrescription
    CompanyForest Labs

    2 of 2  
    Drug NameViibryd
    PubMed HealthVilazodone (By mouth)
    Drug ClassesAntidepressant
    Drug LabelVIIBRYD Tablets for oral administration contain polymorph Form IV vilazodone hydrochloride (HCl), a selective serotonin reuptake inhibitor and a 5HT1A receptor partial agonist.Vilazodone HCl is 2-benzofurancarboxamide, 5-[4-[4-(5-cyano-1H-indol-3-yl)...
    Active IngredientVilazodone hydrochloride
    Dosage FormTablet
    RouteOral
    Strength10mg; 40mg; 20mg
    Market StatusPrescription
    CompanyForest Labs

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antidepressive Agents

    Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

    Selective Serotonin Reuptake Inhibitors

    Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Selective Serotonin Reuptake Inhibitors.)

    Serotonin 5-HT1 Receptor Agonists

    Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)