General Information of Drug (ID: DM4LECQ)

Drug Name
Vilazodone
Synonyms Vilazodone [INN]; Vilazodone (TN); 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]benzofuran-2-carboxamide
Indication
Disease Entry ICD 11 Status REF
Major depressive disorder 6A70.3 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 441.5
Logarithm of the Partition Coefficient (xlogp) 4
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 7 h [2]
Clearance
The clearance of drug is 19.9-25.1 L/h [3]
Elimination
1% of the dose is recovered unchanged in the urine and 2% of the dose is recovered unchanged in the feces [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 25 hours [3]
Metabolism
The drug is metabolized via the cytochrome P450(CYP)3A4 and also to a minor extent by CYP2C19 and CYP 2D6 [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.03% [6]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 4.85 L/kg [6]
Chemical Identifiers
Formula
C26H27N5O2
IUPAC Name
5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide
Canonical SMILES
C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N
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
Cross-matching ID
PubChem CID
6918314
ChEBI ID
CHEBI:70707
CAS Number
163521-12-8
DrugBank ID
DB06684
TTD ID
D0X6BV
VARIDT ID
DR00915
INTEDE ID
DR1687
ACDINA ID
D00728

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 1A receptor (HTR1A) TTSQIFT 5HT1A_HUMAN Modulator [7]
Serotonin transporter (SERT) TT3ROYC SC6A4_HUMAN Modulator [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME
DE4LYSA CP3A4_HUMAN Substrate [8]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [8]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Major depressive disorder
ICD Disease Classification 6A70.3
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 1A receptor (HTR1A) DTT HTR1A 2.18E-01 -0.11 -0.51
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 6.32E-02 1.30E-01 7.89E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 5.49E-01 5.15E-02 1.92E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 3.40E-01 1.04E-01 7.11E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 7.43E-01 2.19E-03 1.72E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 3.18E-03 2.30E-01 2.71E+00
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 8.32E-01 4.74E-02 1.73E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Vilazodone
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Vortioxetine DM6F1PU Major Additive serotonergic effects by the combination of Vilazodone and Vortioxetine. Depression [6A70-6A7Z] [9]
Desvenlafaxine DMHD4PE Major Additive serotonergic effects by the combination of Vilazodone and Desvenlafaxine. Depression [6A70-6A7Z] [9]
Coadministration of a Drug Treating the Disease Different from Vilazodone (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Major Additive serotonergic effects by the combination of Vilazodone and Methylene blue. Acquired methaemoglobinaemia [3A93] [10]
Ivosidenib DM8S6T7 Moderate Increased metabolism of Vilazodone caused by Ivosidenib mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [11]
Arn-509 DMT81LZ Moderate Increased metabolism of Vilazodone caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [11]
Oliceridine DM6MDCF Moderate Additive serotonergic effects by the combination of Vilazodone and Oliceridine. Acute pain [MG31] [12]
Inotersen DMJ93CT Moderate Increased risk of bleeding by the combination of Vilazodone and Inotersen. Amyloidosis [5D00] [13]
Troleandomycin DMUZNIG Major Decreased metabolism of Vilazodone caused by Troleandomycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [11]
Pexidartinib DMS2J0Z Moderate Increased metabolism of Vilazodone caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [11]
Tucatinib DMBESUA Major Decreased metabolism of Vilazodone caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [11]
Regorafenib DMHSY1I Moderate Increased risk of bleeding by the combination of Vilazodone and Regorafenib. Colorectal cancer [2B91] [13]
Ardeparin DMYRX8B Moderate Increased risk of bleeding by the combination of Vilazodone and Ardeparin. Coronary thrombosis [BA43] [13]
Lumacaftor DMCLWDJ Moderate Increased metabolism of Vilazodone caused by Lumacaftor mediated induction of CYP450 enzyme. Cystic fibrosis [CA25] [11]
Ivacaftor DMZC1HS Moderate Decreased metabolism of Vilazodone caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [11]
MK-8228 DMOB58Q Moderate Decreased metabolism of Vilazodone caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [11]
Danaparoid DM6CLBN Moderate Increased risk of bleeding by the combination of Vilazodone and Danaparoid. Deep vein thrombosis [BD71] [13]
Stiripentol DMMSDOY Moderate Decreased metabolism of Vilazodone caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [14]
Eslicarbazepine DMZREFQ Moderate Increased risk of hyponatremia by the combination of Vilazodone and Eslicarbazepine. Epilepsy/seizure [8A61-8A6Z] [15]
Tazemetostat DMWP1BH Moderate Increased metabolism of Vilazodone caused by Tazemetostat mediated induction of CYP450 enzyme. Follicular lymphoma [2A80] [11]
Avapritinib DMK2GZX Moderate Increased risk of bleeding by the combination of Vilazodone and Avapritinib. Gastrointestinal stromal tumour [2B5B] [13]
Boceprevir DMBSHMF Major Decreased metabolism of Vilazodone caused by Boceprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [11]
Cobicistat DM6L4H2 Major Decreased metabolism of Vilazodone caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [11]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Vilazodone and Polyethylene glycol. Irritable bowel syndrome [DD91] [16]
Crizotinib DM4F29C Moderate Decreased metabolism of Vilazodone caused by Crizotinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Ceritinib DMB920Z Major Decreased metabolism of Vilazodone caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
PF-06463922 DMKM7EW Moderate Increased metabolism of Vilazodone caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [11]
Selpercatinib DMZR15V Moderate Decreased metabolism of Vilazodone caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [11]
Idelalisib DM602WT Major Decreased metabolism of Vilazodone caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [11]
IPI-145 DMWA24P Moderate Decreased metabolism of Vilazodone caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [11]
Acalabrutinib DM7GCVW Moderate Increased risk of bleeding by the combination of Vilazodone and Acalabrutinib. Mature B-cell lymphoma [2A85] [13]
Ibrutinib DMHZCPO Moderate Increased risk of bleeding by the combination of Vilazodone and Ibrutinib. Mature B-cell lymphoma [2A85] [13]
Ponatinib DMYGJQO Moderate Increased risk of bleeding by the combination of Vilazodone and Ponatinib. Mature B-cell lymphoma [2A85] [13]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Vilazodone caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [11]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Vilazodone and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [17]
Ozanimod DMT6AM2 Moderate Additive serotonergic effects by the combination of Vilazodone and Ozanimod. Multiple sclerosis [8A40] [18]
Vorapaxar DMA16BR Moderate Increased risk of bleeding by the combination of Vilazodone and Vorapaxar. Myocardial infarction [BA41-BA43] [13]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Vilazodone caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [19]
Abametapir DM2RX0I Moderate Decreased metabolism of Vilazodone caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [20]
Lefamulin DME6G97 Moderate Decreased metabolism of Vilazodone caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [21]
Choline salicylate DM8P137 Moderate Increased risk of bleeding by the combination of Vilazodone and Choline salicylate. Postoperative inflammation [1A00-CA43] [13]
Enzalutamide DMGL19D Moderate Increased metabolism of Vilazodone caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [11]
Selexipag DMAHSU0 Moderate Decreased metabolism of Vilazodone caused by Selexipag mediated inhibition of CYP450 enzyme. Pulmonary hypertension [BB01] [22]
Voxelotor DMCS6M5 Moderate Decreased metabolism of Vilazodone caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [11]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Vilazodone caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [23]
Larotrectinib DM26CQR Moderate Decreased metabolism of Vilazodone caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [24]
LEE011 DMMX75K Moderate Decreased metabolism of Vilazodone caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [11]
Plicamycin DM7C8YV Moderate Increased risk of bleeding by the combination of Vilazodone and Plicamycin. Testicular cancer [2C80] [13]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Vilazodone caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [25]
Brilinta DMBR01X Moderate Increased risk of bleeding by the combination of Vilazodone and Brilinta. Thrombosis [DB61-GB90] [13]
Cabozantinib DMIYDT4 Moderate Increased risk of bleeding by the combination of Vilazodone and Cabozantinib. Thyroid cancer [2D10] [13]
Insulin degludec DMPL395 Moderate Increased risk of hypoglycemia by the combination of Vilazodone and Insulin degludec. Type-1/2 diabete [5A10-5A11] [26]
Elagolix DMB2C0E Moderate Increased metabolism of Vilazodone caused by Elagolix mediated induction of CYP450 enzyme. Uterine fibroid [2E86] [11]
Betrixaban DM2C4RF Moderate Increased risk of bleeding by the combination of Vilazodone and Betrixaban. Venous thromboembolism [BD72] [13]
⏷ Show the Full List of 51 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
FD&C blue no. 1 E00263 19700 Colorant
Sunset yellow FCF E00255 17730 Colorant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Vilazodone 10 mg tablet 10 mg Oral Tablet Oral
Vilazodone 20 mg tablet 20 mg Oral Tablet Oral
Vilazodone 40 mg tablet 40 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7427).
2 Eastman RT, Roth JS, Brimacombe KR, Simeonov A, Shen M, Patnaik S, Hall MD: Remdesivir: A Review of Its Discovery and Development Leading to Emergency Use Authorization for Treatment of COVID-19. ACS Cent Sci. 2020 May 27;6(5):672-683. doi: 10.1021/acscentsci.0c00489. Epub 2020 May 4.
3 Pharmacokinetics of vilazodone in patients with mild or moderate renal impairment. Clin Drug Investig. 2013 Mar;33(3):199-206. doi: 10.1007/s40261-013-0061-5.
4 Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31.
5 Finnen MJ, Herdman ML, Shuster S: Induction of drug metabolising enzymes in the skin by topical steroids. J Steroid Biochem. 1984 May;20(5):1169-73. doi: 10.1016/0022-4731(84)90362-5.
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 2011 FDA drug approvals. Nat Rev Drug Discov. 2012 Feb 1;11(2):91-4.
8 Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31.
9 Achamallah NS "Visual hallucinations after combining fluoxetine and dextromethorphan ." Am J Psychiatry 149 (1992): 1406. [PMID: 1530079]
10 Boyer EW, Shannon M "The serotonin syndrome." N Engl J Med 352 (2005): 1112-20. [PMID: 15784664]
11 Product Information. Viibryd (vilazodone). Trovis Pharmaceuticals LLC, New Haven, CT.
12 Vizcaychipi MP, Walker S, Palazzo M "Serotonin syndrome triggered by tramadol." Br J Anaesth 99 (2007): 919. [PMID: 18006535]
13 Alderman CP, Moritz CK, Ben-Tovim DI "Abnormal platelet aggregation associated with fluoxetine therapy." Ann Pharmacother 26 (1992): 1517-9. [PMID: 1482806]
14 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
15 Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
16 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
17 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
18 Alvine G, Black DW, Tsuang D "Case of delirium secondary to phenelzine/L-tryptophan combination." J Clin Psychiatry 51 (1990): 311. [PMID: 2365671]
19 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
20 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
21 Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
22 Product Information. Uptravi (selexipag). Actelion Pharmaceuticals US Inc, South San Francisco, CA.
23 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
24 Cerner Multum, Inc. "Australian Product Information.".
25 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
26 Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]