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

General Information of Drug (ID: DR1739)
Drug Name
Zotepine
Synonyms
Zoleptil; Zotepina; Zotepina [INN-Spanish]; Zotepina [Spanish]; Zotepinum; Zotepinum [INN-Latin]; Lodopin; Nipolept; Compound-4; HDOZVRUNCMBHFH-UHFFFAOYSA-N; U29O83JAZW; zotepine; 2-Chlor-11-(2-dimethylaminoaethoxy)-dibenzo(b,f)-thiepin; 2-Chloro-11-(2-(dimethylamino)ethoxy)dibenzo(b,f)thiepin; 2-Chloro-11-(2-dimethylaminoethoxy)-dibenzo(b,f)thiepine; 2-[(8-chlorodibenzo[b,f]thiepin-10-yl)oxy]-N,N-dimethylethanamine; 26615-21-4; BRN 1435710; C18H18ClNOS; CHEBI:32316; CHEMBL285802; NCGC00182081-02; UNII-U29O83JAZW
Indication Schizophrenia [ICD11: 6A20] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 331.9 Topological Polar Surface Area 37.8
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5736
PubChem SID
5375173 ; 7848384 ; 7980920 ; 8153517 ; 12013422 ; 14899864 ; 29224773 ; 48416715 ; 49658668 ; 49832081 ; 49962436 ; 57322922 ; 74607145 ; 85174240 ; 85209606 ; 85753334 ; 91749410 ; 92729688 ; 103195284 ; 103993496 ; 104310109 ; 109613401 ; 114919769 ; 118313787 ; 124893805 ; 124893806 ; 125346524 ; 128045577 ; 131308055 ; 134341323 ; 134996843 ; 135651367 ; 137001502 ; 142405042 ; 144206686 ; 162175576 ; 162248926 ; 164829244 ; 170465934 ; 175611849 ; 179150247 ; 198951716 ; 224543978 ; 226486877 ; 250133641 ; 252157701 ; 252418861 ; 252450828
ChEBI ID
CHEBI:32316
CAS Number
26615-21-4
TTD Drug ID
D0T6QX
Formula
C18H18ClNOS
Canonical SMILES
CN(C)CCOC1=CC2=CC=CC=C2SC3=C1C=C(C=C3)Cl
InChI
1S/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3
InChIKey
HDOZVRUNCMBHFH-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
2-OH-zotepine DM015814
12882318
Oxidation - Aromatic hydroxylation 1 [4]
3-OH-zotepine DM015815
12882320
Oxidation - Aromatic hydroxylation 1 [4]
Norzotepine DM015604
10041551
Oxidation - N-demethylation 1 [4] , [5]
Zotepine N-oxide DM015826
13309858
Oxidation - N-oxidation 1 [4]
Zotepine S-oxide DM015813
12882299
Oxidation - S-oxidation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013081 Zotepine Norzotepine Oxidation - N-demethylation CYP1A1 ... [4], [5]
MR013082 Zotepine Zotepine N-oxide Oxidation - N-oxidation CYP3A4 ... [4]
MR013083 Zotepine 2-OH-zotepine Oxidation - Aromatic hydroxylation CYP1A2 [4]
MR013084 Zotepine 3-OH-zotepine Oxidation - Aromatic hydroxylation CYP1A1 ... [4]
MR013085 Zotepine Zotepine S-oxide Oxidation - S-oxidation CYP1A1 ... [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
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]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 8  DME(s)
References
1 ClinicalTrials.gov (NCT00418873) Zotepine Versus Risperidone in Aggressive Schizophrenic Patients of Acute Ward.
2 Identification of cytochrome P450 enzymes involved in the metabolism of zotepine, an antipsychotic drug, in human liver microsomes. Xenobiotica. 1999 Mar;29(3):217-29.
3 New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update. Curr Opin Investig Drugs. 2002 Jul;3(7):1073-80.
4 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.
5 Norzotepine, a major metabolite of zotepine, exerts atypical antipsychotic-like and antidepressant-like actions through its potent inhibition of norepinephrine reuptake

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