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Chemistry

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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

Vilazodone Hydrochloride
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

Vilazodone Hydrochloride

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.)


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