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

General Information of Drug (ID: DR1033)
Drug Name
Mesoridazine
Synonyms
Mesoridazina; Mesoridazina [INN-Spanish]; Mesoridazinum; Mesoridazinum [INN-Latin]; NC-123; Serentil; T-2-SO; THD-2-SO; TPS 23; TPS-23; Calodal; Lidanar; Lidanil; Thioridazien thiomethyl sulfoxide; Thioridazine monosulfoxide analog; Thioridazine thiomethyl sulfoxide; Thioridazine-2-sulfoxide; mesoridazine; 10-(2-(1-Methyl-2-piperidinyl)ethyl)-2-(methylsulfinyl)-10H-phenothiazine; 10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylsulfinyl phenothiazine; 5588-33-0; C21H26N2OS2; CHEBI:6780; CHEMBL1088; HSDB 3357; NSC 186066; NSC186066; Tps23
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 386.6 Topological Polar Surface Area 68.1
Heavy Atom Count 26 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4078
PubChem SID
9352 ; 447728 ; 614172 ; 4379956 ; 7979909 ; 8140528 ; 8152557 ; 10319751 ; 10527260 ; 11405940 ; 11467677 ; 11486174 ; 14927472 ; 17396840 ; 26756521 ; 29223187 ; 46506724 ; 47440446 ; 47440447 ; 47662489 ; 47885582 ; 48035319 ; 48035320 ; 48416224 ; 49699103 ; 50006596 ; 50111387 ; 50111388 ; 50704712 ; 57322129 ; 85209561 ; 85787941 ; 85788345 ; 92309158 ; 96099906 ; 103301322 ; 104022598 ; 104222090 ; 104305362 ; 124892406 ; 125672983 ; 129255022 ; 134337566 ; 134988360 ; 137248555 ; 139029518 ; 144203603 ; 144205571 ; 160964272 ; 163157019
ChEBI ID
CHEBI:6780
CAS Number
5588-33-0
TTD Drug ID
D04AAN
Formula
C21H26N2OS2
Canonical SMILES
CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)S(=O)C
InChI
1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChIKey
SLVMESMUVMCQIY-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Formaldehyde DM001748
712
Oxidation - N-Dealkylation from CyProduct 1 Human
Mesoridazine M10 PDM007246
31765
Oxidation - S-Oxidation of sulfoxide to sulfone AndFromCyProduct 1 Human
Mesoridazine M11 PDM007247 N. A. Oxidation - Hydroxylation from CyProduct 1 Human
Mesoridazine M17 PDM007253
5452
Reduction - Reduction of sulfoxide to thioether 1 Human
Mesoridazine M18 PDM007254
14289610
Oxidation - N-Dealkylation of mixed tertiary amine 1 Human
Mesoridazine M19 PDM007255
12311333
Oxidation - N-Dealkylation of mixed tertiary amine 1 Human
Mesoridazine M20 PDM007256
89225169
Oxidation - N-Oxidation of alicyclic tertiary amine 1 Human
Mesoridazine M21 PDM007257 N. A. Oxidation - Aliphatic hydroxylation of carbon alpha to secondary or tertiary alkyl-N 1 Human
Mesoridazine M21 PDM007257 N. A. Oxidation - Hydroxylation of heteroalicyclic secondary carbon 1 Human
Mesoridazine M22 PDM007258 N. A. Oxidation - Hydroxylation of heteroalicyclic secondary carbon 1 Human
Mesoridazine M23 PDM007259 N. A. Oxidation - Hydroxylation of heteroalicyclic secondary carbon 1 Human
Mesoridazine M24 PDM007260 N. A. Oxidation - Aliphatic hydroxylation of carbon alpha to secondary or tertiary alkyl-N 1 Human
Mesoridazine M25 PDM007261 N. A. Oxidation - Aliphatic hydroxylation of carbon alpha to secondary or tertiary alkyl-N 1 Human
Mesoridazine M27 PDM007262 N. A. Other reaction - Formation of imminium ion from N-substituted piperidine 1 Human
Mesoridazine M28 PDM007263 N. A. Other reaction - Formation of imminium ion from N-substituted piperidine 1 Human
Mesoridazine M4 PDM007240 N. A. Oxidation - Aromatic hydroxylation of fused benzene ring AndFromCyProduct 1 Human
Mesoridazine M5 PDM007241 N. A. Oxidation - Aromatic hydroxylation of fused benzene ring AndFromCyProduct 1 Human
Mesoridazine M6 PDM007242 N. A. Oxidation - Aromatic hydroxylation of fused benzene ring AndFromCyProduct 1 Human
Mesoridazine M7 PDM007243 N. A. Oxidation - Hydroxylation from CyProduct 1 Human
Mesoridazine M8 PDM007244
567069
Oxidation - S-Oxidation of diarylthioether to sulfoxide AndFromCyProduct 1 Human
Mesoridazine M9 PDM007245
31753
Oxidation - N-Dealkylation of alicyclic tertiary amine AndFromCyProduct 1 Human
Mesoridazine M13 PDM007249 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
Mesoridazine M14 PDM007250 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
Mesoridazine M15 PDM007251 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
Mesoridazine M16 PDM007252 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
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]
References
1 Mesoridazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.

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