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

General Information of Drug (ID: DR1135)
Drug Name
Nefazodone
Synonyms
Nefadar; Nefazodona; Nefazodona [Spanish]; Nefazodone [INN:BAN]; Nefazodonum; Nefazodonum [Latin]; VRBKIVRKKCLPHA-UHFFFAOYSA-N; nefazodone; 1-(3-(4-(3-Chlorophenyl)piperazin-1-yl)propyl)-3-ethyl-4-(2-phenoxyethyl)-1H-1,2,4-triazol-5(4H)-one; 1-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-3-ethyl-4-(2-phenoxyethyl)-delta2-1,2,4-triazolin-5-one; 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-5-ethyl-4-(2-phenoxyethyl)-1,2,4-triazol-3-one; 59H4FCV1TF; 83366-66-9; CHEBI:7494; CHEMBL623; UNII-59H4FCV1TF
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 470 Topological Polar Surface Area 51.6
Heavy Atom Count 33 Rotatable Bond Count 10
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4449
PubChem SID
9465 ; 4634333 ; 7980102 ; 8152743 ; 14858579 ; 29217604 ; 29223544 ; 46508323 ; 48416316 ; 49665930 ; 49666410 ; 50057418 ; 50111710 ; 50788542 ; 56464118 ; 57322274 ; 85209875 ; 85789114 ; 89736110 ; 92309073 ; 93166947 ; 96024945 ; 103188221 ; 103963508 ; 104306436 ; 121362268 ; 124799827 ; 124893191 ; 125358294 ; 126656776 ; 126684012 ; 127339542 ; 127339543 ; 127339544 ; 127339545 ; 129514880 ; 131327475 ; 134337370 ; 135020756 ; 137001425 ; 142052543 ; 144076337 ; 152046617 ; 160964483 ; 163409603 ; 164828567 ; 172862753 ; 175268308 ; 175610915 ; 176484419
ChEBI ID
ChEBI:7494
CAS Number
83366-66-9
TTD Drug ID
D0X7DE
Formula
C25H32ClN5O2
Canonical SMILES
CCC1=NN(C(=O)N1CCOC2=CC=CC=C2)CCCN3CCN(CC3)C4=CC(=CC=C4)Cl
InChI
1S/C25H32ClN5O2/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22/h3-6,8-11,20H,2,7,12-19H2,1H3
InChIKey
VRBKIVRKKCLPHA-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
1-(3-chlorophenyl) piperazine DM002369
1355
Unclear 1 [4]
3-[3-ethyl-5-oxo-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanal DM004560 N. A. Oxidation - N-dealkylation 1 [5]
Hydroxynefazodone DM004555
11755137
Oxidation - Hydrolyzationn 1 [5]
Nefazodone Metabolite E DM004557 N. A. Unclear 1 [4]
1-(3-chlorophenyl) piperazine DM002369
1355
Oxidation - N-dealkylation 2 [4]
1-(3-chlorophenyl) piperazine DM002369
1355
Unclear 2 [4]
Nefazodone Metabolite D DM004558 N. A. Unclear 2 [4]
p-hydroxy-mCPP DM004556 N. A. Unclear 2 [4]
Triazoledione DM004561
9804174
Unclear 2 [4]
Nefazodone Metabolite C DM004559 N. A. Unclear 3 [4]
p-hydroxy-mCPP DM004556 N. A. Unclear 3 [4]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004885 Nefazodone Hydroxynefazodone Oxidation - Hydrolyzationn CYP3A4 [5]
MR004888 Nefazodone Nefazodone Metabolite E Unclear Unclear [4]
MR004891 Nefazodone M-Chlorophenylpiperazine Unclear Unclear [4]
MR004892 Nefazodone 3-[3-ethyl-5-oxo-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanal Oxidation - N-dealkylation CYP3A4 [5]
MR004886 Hydroxynefazodone M-Chlorophenylpiperazine Unclear Unclear [4]
MR004893 Hydroxynefazodone Triazoledione Unclear Unclear [4]
MR004889 Nefazodone Metabolite E Nefazodone Metabolite D Unclear Unclear [4]
MR004887 M-Chlorophenylpiperazine p-hydroxy-mCPP Unclear Unclear [4]
MR004890 Nefazodone Metabolite D Nefazodone Metabolite C Unclear Unclear [4]
⏷ Show the Full List of 9 MR(s)
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]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [3]
References
1 Nefazodone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Nefazodone, meta-chlorophenylpiperazine, and their metabolites in vitro: cytochromes mediating transformation, and P450-3A4 inhibitory actions. Psychopharmacology (Berl). 1999 Jul;145(1):113-22.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Clinical pharmacokinetics of nefazodone. Clin Pharmacokinet. 1997 Oct;33(4):260-75.
5 DrugBank(Pharmacology-Metabolism):Nefazodone

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