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

General Information of Drug (ID: DR1581)
Drug Name
Thioridazine
Synonyms
Thioridazin; Thioridazine prolongatum; Thioridazine, prolongatum; Thioridazinum; Thioridazinum [INN-Latin]; Tioridazin; Tioridazina; Tioridazina [INN-Spanish]; Mallorol; Malloryl; Meleril; Mellaril; Mellaril-S; Mellarit; Mellerets; Mellerette; Melleretten; Melleril; Melleril (liquid); Melleryl; Metlaril; Orsanil; Ridazine; Sonapax; dl-Thioridazine; thioridazine; (+-)-Thioridazine; 10-(2-(1-Methylpiperidin-2-yl)ethyl)-2-(methylthio)-10H-phenothiazine; 2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazine; 50-52-2; TP-21
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 370.6 Topological Polar Surface Area 57.1
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5452
PubChem SID
616470 ; 5646742 ; 7847439 ; 7980776 ; 8153353 ; 10524427 ; 11335241 ; 11360480 ; 11363960 ; 11364721 ; 11366522 ; 11367283 ; 11369084 ; 11369845 ; 11371630 ; 11372886 ; 11373930 ; 11375445 ; 11377246 ; 11378009 ; 11461452 ; 11466106 ; 11467226 ; 11485219 ; 11485952 ; 11489148 ; 11490401 ; 11492171 ; 11494880 ; 12013415 ; 14804036 ; 26752322 ; 29224497 ; 46509070 ; 47216619 ; 47216620 ; 47290971 ; 47440079 ; 47515153 ; 47515154 ; 47588829 ; 47810593 ; 48110292 ; 48334314 ; 48334315 ; 48416615 ; 49658718 ; 49698892 ; 50006598 ; 50105272
ChEBI ID
ChEBI:9566
CAS Number
50-52-2
TTD Drug ID
D0U1OE
Formula
C21H26N2S2
Canonical SMILES
CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)SC
InChI
1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChIKey
KLBQZWRITKRQQV-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
Hydroxy-Thioridazine DM004616 N. A. Unclear 1 [5]
N-desmethylthioridazine DM004614
558813
Oxidation - N-dealkylation 1 [2]
Thioridazine 2-sulfoxide DM003069
4078
Oxidation - S-oxidation 1 [2]
Thioridazine 5-sulfoxide DM004615
24494
Oxidation - S-oxidation 1 [2]
Sulforidazine DM004613
31765
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004957 Thioridazine Thioridazine 2-sulfoxide Oxidation - S-oxidation CYP2D6 ... [2]
MR004959 Thioridazine N-desmethylthioridazine Oxidation - N-dealkylation CYP1A2 ... [2]
MR004960 Thioridazine Thioridazine 5-sulfoxide Oxidation - S-oxidation CYP1A2 ... [2]
MR004961 Thioridazine Hydroxy-Thioridazine Unclear Unclear [5]
MR004958 Thioridazine 2-sulfoxide Sulforidazine Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
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
[4]
References
1 Thioridazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Extraction of structure-activity relationship information from high-throughput screening data Curr Med Chem. 2009;16(31):4049-57. doi: 10.2174/092986709789378189.
3 Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype. Eur J Clin Pharmacol. 2003 May;59(1):45-50.
4 CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob Agents Chemother. 2013 Nov;57(11):5448-56.
5 Pharmacokinetics and metabolism of thioridazine during co-administration of tricyclic antidepressants

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