Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1687)
Drug Name
Vilazodone hydrochloride
Synonyms
Vilazodone (Hydrochloride); Vilazodone HCl; Vilazodone hydrochloride; Vilazodone hydrochloride (USAN); Vilazodone hydrochloride [USAN]; Vilazodone; 163521-12-8; 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]-1-piperazinyl]-2-benzofurancarboxamide; 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; 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide; CHEBI:70707; CHEMBL439849; EMD 515259; EMD-515259; EMD-68-843; S239O2OOV3; UNII-S239O2OOV3; 163521-08-2; 5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide hydrochloride; 5-[4-[4-(5-Cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxamide hydrochloride; AK161007; CHEBI:70705; EMD 68 843; EMD 68843; SB 659746A; SB-659746A; SB659746A; U8HTX2GK8J; UNII-U8HTX2GK8J; Viibryd
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 478 Topological Polar Surface Area 102
Heavy Atom Count 34 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
6918313
ChEBI ID
CHEBI:70705
CAS Number
163521-08-2
TTD Drug ID
D0X6BV
Formula
C26H28ClN5O2
Canonical SMILES
C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)N.Cl
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
InChIKey
RPZBRGFNBNQSOP-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Vilazodone metabolite M10 DM005269
11201569
Multi-steps Reaction - Oxidationn deamination 1 [2] , [4] , [5]
Vilazodone metabolite M13 DM005267
11201934
Oxidation - Hydrolyzationn 1 [4]
Vilazodone metabolite M17 DM005270
18330301
Unclear 1 [4]
Vilazodone metabolite M21 DM020010 N. A. Oxidation - sulfonation 2 [4]
Vilazodone metabolite M4 DM005268
156596404
Conjugation - Glucuronidation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013235 Vilazodone hydrochloride Vilazodone metabolite M13 Oxidation - Hydrolyzationn Unclear [4]
MR013238 Vilazodone hydrochloride Vilazodone metabolite M10 Multi-steps Reaction - Oxidationn deamination CYP3A4 ... [2], [4], [5]
MR013239 Vilazodone hydrochloride Vilazodone metabolite M17 Unclear Unclear [4]
MR013236 Vilazodone metabolite M13 Vilazodone metabolite M4 Conjugation - Glucuronidation Unclear [4]
MR013237 Vilazodone metabolite M13 Vilazodone metabolite M21 Oxidation - sulfonation [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [3]
⏷ Show the Full List of 24  DME(s)
References
1 Vilazodone Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Accidental intoxications in toddlers: lack of cross-reactivity of vilazodone and its urinary metabolite M17 with drug of abuse screening immunoassays
5 DETERMINATION OF VENLAFAXINE, VILAZODONE AND THEIR MAIN ACTIVE METABOLITES IN HUMAN SERUM BY HPLC-DAD AND HPLC-MS

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