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

General Information of Drug (ID: DR1631)
Drug Name
Trazodone hydrochloride
Synonyms
Thombran; Tombran; Trazodone (hydrochloride); Trazodone Hcl; Trazodone hydrochloride; Trazodone hydrochloride (Desyrel); Tritico; Triticum; Trazalon; Trazodil; Trazodon; Trazodona; Trazodona [INN-Spanish]; Trazodona [Spanish]; Trazodone [INN:BAN]; Trazodonum; Trazodonum [INN-Latin]; Trazodonum [Latin]; Trazonil; Trialodine; UNII-YBK48BXK30; YBK48BXK30; s-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-; Trazodone; 19794-93-5; BRN 0628010; Beneficat; C19H22ClN5O; CHEBI:9654; CHEMBL621; Desirel; EINECS 243-317-1; PHLBKPHSAVXXEF-UHFFFAOYSA-N; Sideril; UNII-6E8ZO8LRNM; 2-(3-(4-(m-Chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2H)-one monohydrochloride; 25332-39-2; 6E8ZO8LRNM; AF 1161; AF-1161; Apo-Trazodone; Azona; Bimaran; CHEBI:9655; DSSTox_RID_80361; Devidon; EINECS 246-855-5; HSDB 7048; KB-831; MFCD00079603; MLS000069698; NSC 292811; Pragmazone; SMR000058520
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 408.3 Topological Polar Surface Area 42.4
Heavy Atom Count 27 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
62935
ChEBI ID
CHEBI:9655
CAS Number
19666-36-5
TTD Drug ID
D00USF
Formula
C19H23Cl2N5O
Canonical SMILES
C1CN(CCN1CCCN2C(=O)N3C=CC=CC3=N2)C4=CC(=CC=C4)Cl.Cl
InChI
1S/C19H22ClN5O.ClH/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25;/h1-3,5-7,9,15H,4,8,10-14H2;1H
InChIKey
OHHDIOKRWWOXMT-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
Oxidation - N-Dealkylation 1 [5]
4'-hydroxytrazodone DM002366
46781917
Oxidation - Hydroxylation 1 [3]
Triazolopyridinone epoxide DM002362
131770015
Unclear 1 [3]
Trazodone hydrochloride M2 DM002363 N. A. Unclear 2 [3]
Trazodone hydrochloride M3 DM002364 N. A. Conjugation - Glutathione Conjugation 2 [3]
Trazodone hydrochloride M6 DM002367 N. A. Conjugation - Glutathione Conjugation 2 [3]
Trazodone hydrochloride MQ DM002365 N. A. Unclear 2 [3]
Trazodone hydrochloride MW DM002368 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002442 Trazodone hydrochloride Triazolopyridinone epoxide Unclear CYP3A4 [3]
MR002443 Trazodone hydrochloride 4'-hydroxytrazodone Oxidation - Hydroxylation Unclear [3]
MR002444 Trazodone hydrochloride M-chlorophenylpiperazine Oxidation - N-Dealkylation CYP3A4 [5]
MR002440 4'-hydroxytrazodone Trazodone hydrochloride M6 Conjugation - Glutathione Conjugation Unclear [3]
MR002441 4'-hydroxytrazodone Trazodone hydrochloride MW Unclear Unclear [3]
MR002437 Triazolopyridinone epoxide Trazodone hydrochloride M2 Unclear Unclear [3]
MR002438 Triazolopyridinone epoxide Trazodone hydrochloride M3 Conjugation - Glutathione Conjugation Unclear [3]
MR002439 Triazolopyridinone epoxide Trazodone hydrochloride MQ Unclear Unclear [3]
⏷ Show the Full List of 8 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
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
References
1 Trazodone Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Evaluating the role of drug metabolism and reactive intermediates in trazodone-induced cytotoxicity toward freshly-isolated rat hepatocytes. Drug Res (Stuttg). 2016 Nov;66(11):592-596.
3 Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20.
4 Drug Interactions Flockhart Table
5 Pharmacokinetics of trazodone and its major metabolite m-chlorophenylpiperazine in plasma and brain of rats Int J Neuropsychopharmacol. 1999 Mar;2(1):17-23. doi: 10.1017/S1461145799001303.

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