Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00728)
Name
Vilazodone
Synonyms    Click to Show/Hide the Synonyms of This API
Vilazodone; 163521-12-8; 5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide; UNII-S239O2OOV3; EMD 515259; CHEMBL439849; S239O2OOV3; CHEBI:70707; 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]piperazin-1-yl}-1-benzofuran-2-carboxamide; EMD-515259; EMD-68-843; 2-BENZOFURANCARBOXAMIDE, 5-[4-[4-(5-CYANO-1H-INDOL-3-YL)BUTYL]-1-PIPERAZINYL]-; EMD 68843 (Hydrochloride);SB659746A (Hydrochloride); SB 659746A; SB-659746-A; Vilazodone [USAN:INN]; vilazodona; vilazodonum; HSDB 8197; Vilazodone (USAN/INN); 5-[4-[4-(5-Cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-benzofurancarboxamide; cc-127; SCHEMBL650682; GTPL7427; yl}-1-benzofuran-2-carboxamide; EX-A174; QCR-275; HMS3744C03; HMS3886N05; BCP05225; ZINC1542113; ANW-63936; BDBM50151982; MFCD09838919; 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine; AKOS015924744; CS-0550; DB06684; PB25213; SB20296; NCGC00371130-03; NCGC00371130-06; AC-25886; AS-73542; HY-14262; AB0044260; EMD 68843;SB 659746A; FT-0675813; D09698; Q-4354; AB01563299_01; L001518; Q408588; 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-; F0001-2418; 1-[4-(5-cyanoindol-3-yl)butyl]4-(2-carbamoyl-benzofuran-5-yl)-piperazine; 5-(4-(4-(5-Cyanoindol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxamide; 5-{4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl}benzo-furan-2-carboxamide; 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine; 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-carboxylic acid amide
Clinical Status
Approved
Disease Indication Major depressive disorder ICD-11: 6A70 [1]
PubChem CID
6918314
Formula
C26H27N5O2
Canonical SMILES
C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6918314"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 441.5 Topological Polar Surface Area 102
XlogP 4 Complexity 729
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Vilazodone 10 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c red no. 40; Magnesium stearate; Talc; Titanium dioxide; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Allergan; Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Vilazodone 20 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Allergan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Silicon dioxide; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified
                   Dosage Form Oral Tablet
                   Company Cardinal Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Vilazodone 40 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c blue no. 1; Magnesium stearate; Talc; Titanium dioxide; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Allergan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c blue no. 1; Magnesium stearate; Talc; Titanium dioxide; Silicon dioxide; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified
                   Dosage Form Oral Tablet
                   Company Cardinal Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved vilazodone from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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