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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18ClNOS
Molecular Weight 331.8613
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZOTEPINE

SMILES

CN(C)CCOC1=Cc2ccccc2Sc3ccc(cc13)Cl

InChI

InChIKey=HDOZVRUNCMBHFH-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Zotepine is a potent antipsychotic and antidepressive drug, which was developed in Japan and used in many countries for the treatment of schizophrenia. Zotepine has high affinity to D2, 5-HT2A, 5-HT2C, 5-HT6, 5-HT7, alpha1A, H1, and D1 receptors at therapeutically relevant concentrations and has similar affinities to 5-HT1A, alpha2A, and M1 receptors at high concentrations. In human zotepine is metabolized to a major metabolite, norzotepine, which has profile similar to that of zotepine for important neurotransmitter receptors known to be responsible for zotepine antipsychotic activity.The drug is still available in Asia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28223
Gene ID: 3356
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
0.689999999999999947 nM [Ki]
Target ID: P28335
Gene ID: 3358
Gene Symbol: HTR2C
Target Organism: Homo sapiens (Human)
1.29000000000000004 nM [Ki]
Target ID: P14416
Gene ID: 1813
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
2.29999999999999982 nM [Ki]
Target ID: P50406
Gene ID: 3362
Gene Symbol: HTR6
Target Organism: Homo sapiens (Human)
2.89999999999999991 nM [Ki]
Target ID: P35348|||B0ZBD9|||Q6RUJ8
Gene ID: 148
Gene Symbol: ADRA1A
Target Organism: Homo sapiens (Human)
1.19999999999999996 nM [Ki]
Target ID: P34969
Gene ID: 3363
Gene Symbol: HTR7
Target Organism: Homo sapiens (Human)
4.59999999999999964 nM [Ki]
Target ID: P35367
Gene ID: 3269
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
0.469999999999999973 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Schizophrenia.
2005 Dec
Effect of zotepine on dopamine, serotonin and noradrenaline release in rat prefrontal cortex.
2005 Dec 28
[The serotonin syndrome].
2005 Oct
Adverse effects of atypical antipsychotics in the elderly: a review.
2006
Perazine for schizophrenia.
2006 Apr 19
Atypical antipsychotics to treat the neuropsychiatric symptoms of dementia.
2006 Dec
The effectiveness of atypical antipsychotics for the treatment of aggression and psychosis in Alzheimer's disease.
2006 Jan 25
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Investigation of the electrochemical oxidation products of zotepine and their fragmentation using on-line electrochemistry/electrospray ionization mass spectrometry.
2006 May
Efficacy and safety of zotepine for patients with treatment-resistant schizophrenia.
2006 Oct
Zotepine for schizophrenia.
2006 Oct 18
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.
2006 Oct 20
Second-generation antipsychotic agents in the treatment of acute mania: a systematic review and meta-analysis of randomized controlled trials.
2007 Apr
Risk of extrapyramidal syndrome in schizophrenic patients treated with antipsychotics: a population-based study.
2007 Apr
Are there any differences in the efficacy among second generation antipsychotics in the treatment of schizophrenia and related disorders?
2007 Apr-Jun
Current therapeutic options for Alzheimer's disease.
2007 Dec
Differences in the effect of second-generation antipsychotics on prolactinaemia: six weeks open-label trial in female in-patients.
2007 Dec
Long-acting risperidone injection: efficacy, safety, and cost-effectiveness of the first long-acting atypical antipsychotic.
2007 Feb
Atypical antipsychotic drugs: current issues of safety and efficacy in the management of schizophrenia.
2007 Jul
Hypothermia following antipsychotic drug use.
2007 Jun
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
Pharmacological causes of hyperprolactinemia.
2007 Oct
Early prediction of clinical response in schizophrenia patients receiving the atypical antipsychotic zotepine.
2007 Oct
Acute and long-term treatment of mania.
2008
Typical and atypical antipsychotics--the misleading dichotomy. Results from the Working Group 'Drugs in Psychiatry' (AGATE).
2008
[Atypical antipsychotics in first-episode psychosis: a review].
2008 Apr
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913).
2008 Dec 22
Treatment of clozapine-associated tardive dyskinesia.
2008 Feb 15
Cardiac side effects of psychiatric drugs.
2008 Jan
A pharmacoeconomic analysis of atypical antipsychotics and haloperidol in first-episode schizophrenic patients in taiwan.
2008 Jun
Zotepine-induced spontaneous ejaculation.
2008 Nov
Zotepine-induced QTc prolongation.
2008 Oct
Further characterization of the discriminative stimulus properties of the atypical antipsychotic drug clozapine in C57BL/6 mice: role of 5-HT(2A) serotonergic and alpha (1) adrenergic antagonism.
2009 Apr
Sertindole versus other atypical antipsychotics for schizophrenia.
2009 Apr 15
Increased D-amino acid oxidase expression in the bilateral hippocampal CA4 of schizophrenic patients: a post-mortem study.
2009 Dec
Zotepine: a clinical review.
2009 Feb
A meta-analysis of head-to-head comparisons of second-generation antipsychotics in the treatment of schizophrenia.
2009 Feb
Effects of zotepine on extracellular levels of monoamine, GABA and glutamate in rat prefrontal cortex.
2009 Jun
Review of the efficacy of placebo in comparative clinical trials between typical and atypical antipsychotics.
2009 Mar
Application of on-line electrochemistry/electrospray/tandem mass spectrometry to a quantification method for the antipsychotic drug zotepine in human serum.
2009 Oct
Ziprasidone versus other atypical antipsychotics for schizophrenia.
2009 Oct 7
Aripiprazole versus other atypical antipsychotics for schizophrenia.
2009 Oct 7
Impaired prefrontal hemodynamic maturation in autism and unaffected siblings.
2009 Sep 3
Zotepine versus other atypical antipsychotics for schizophrenia.
2010 Jan 20
Quetiapine versus other atypical antipsychotics for schizophrenia.
2010 Jan 20
Amisulpride versus other atypical antipsychotics for schizophrenia.
2010 Jan 20
Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia.
2010 Mar
QTc prolongation and antipsychotic medications in a sample of 1017 patients with schizophrenia.
2010 Mar 17
Prolonged withdrawal delirium in concomitant diphenhydramine and nefopam dependence: A case report.
2010 May 30
Patents

Patents

Sample Use Guides

The usual adult dosage for oral use is 75 mg to 150 mg of zotepine daily in divided doses.
Route of Administration: Oral
Name Type Language
ZOTEPINE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
ZOTEPIN
Common Name English
ZOTEPINE [MART.]
Common Name English
NIPOLEPT
Brand Name English
2-((8-CHLORODIBENZO(B,F)THIEPIN-10-YL)OXY)-N,N-DIMETHYLETHYLAMINE
Systematic Name English
ZOTEPINE [MI]
Common Name English
SETOUS
Brand Name English
ZOTEPINE [INN]
Common Name English
ZOTEPINE [WHO-DD]
Common Name English
ZOTEPINE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
WHO-VATC QN05AX11
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
WHO-ATC N05AX11
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
NCI_THESAURUS C66883
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
Code System Code Type Description
INN
4112
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
NCI_THESAURUS
C81096
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
EVMPD
SUB00191MIG
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL285802
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
CAS
26615-21-4
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
MESH
C022172
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
DRUG BANK
DB09225
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
WIKIPEDIA
ZOTEPINE
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
FDA UNII
U29O83JAZW
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
MERCK INDEX
M11667
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY Merck Index
EPA CompTox
26615-21-4
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
PUBCHEM
5736
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
RXCUI
40003
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY RxNorm
IUPHAR
103
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY
DRUG CENTRAL
2875
Created by admin on Sat Jun 26 12:07:41 UTC 2021 , Edited by admin on Sat Jun 26 12:07:41 UTC 2021
PRIMARY