CYAMEMAZINE TARTRATE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C19H21N3S.C4H6O6
Molecular Weight	473.542
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(CN(C)C)CN1C2=CC=CC=C2SC3=CC=C(C=C13)C#N

InChI

InChIKey=OVSVMCBAXAWPTR-LREBCSMRSA-N

InChI=1S/C19H21N3S.C4H6O6/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22;5-1(3(7)8)2(6)4(9)10/h4-10,14H,12-13H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492772 | https://www.ncbi.nlm.nih.gov/pubmed/12527336

Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class used primarily in the treatment of schizophrenia and psychosis-associated anxiety. Cyamemazine actually behaves like an atypical antipsychotic, due to its potent anxiolytic effects and lack of extrapyramidal side effects. Cyamemazine is used for the treatment of chronic psychotic states, anxiety, major depression.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
D(1A) dopamine receptor 18 Target ID: P21728 Gene ID: 1812.0 Gene Symbol: DRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2778	3.8 nM [Ki]
Dopamine D3 receptor 91 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2778	2.5 nM [Ki]
5-hydroxytryptamine receptor 2A 69 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2778	1.5 nM [Ki]
5-hydroxytryptamine receptor 2C 26 Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2778	12.0 nM [Ki]
Adrenergic receptor alpha 64 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2778	2.3 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492772	Primary	Approved 8429	TERCIAN Approved Use Chronic psychotic states (schizophrenia, chronic non-schizophrenic delusions: paranoid delusions, chronic hallucinatory psychoses).
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492772	Primary	Approved 8429	TERCIAN Approved Use Short-term symptomatic treatment of adult anxiety in case of failure of usual therapies.
Major depression 8 Sources: http://www.doctissimo.fr/medicament-TERCIAN.htm	Primary	Approved 8429	TERCIAN Approved Use In combination with an antidepressant, short-term treatment of some severe forms of major depressive episode.
Alcohol withdrawal 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492772	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hypertonia and malignant hyperthermia due to morphine and neuroleptic.	1981 Feb 14	6110016
Transient ST segment elevation in right precordial leads induced by psychotropic drugs: relationship to the Brugada syndrome.	2001 Jan	11204086
Concentrations of cis(Z)-clopenthixol and trans(E)-clopenthixol in a lethal case involving zuclopenthixol, diazepam, and cyamemazine.	2001 Jul-Aug	11499890
Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice.	2001 Sep 28	11423169
[Pharmaco-epidemiological study on antipsychotic drug prescription in French Psychiatry: Patient characteristics, antipsychotic treatment, and care management for schizophrenia].	2002 Mar-Apr	11972139
[Catatonia de novo, report on a case: immediate vital prognosis and psychiatric prognosis in longer term].	2003 Jan-Feb	12640330
Acute fatal poisoning with cyamemazine.	2003 Oct 14	14550607
Interspecies variability and drug interactions of loxapine metabolism in liver microsomes.	2003 Oct-Dec	14743971
Primary photochemical processes of the phototoxic neuroleptic cyamemazine: a study by laser flash photolysis and steady-state irradiation.	2004 Nov-Dec	15623341
A positron emission tomography (PET) study of cerebral dopamine D2 and serotonine 5-HT2A receptor occupancy in patients treated with cyamemazine (Tercian).	2005 Jul	15948013
Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic.	2005 May	15875075
[Alcohol dependence and depressive disorders in the course of opiate dependence].	2005 Oct	16673707
Double-blind study of cyamemazine and diazepam in the alcohol withdrawal syndrome.	2005 Oct	16118830
Double-blind, comparative study of cyamemazine vs. bromazepam in the benzodiazepine withdrawal syndrome.	2006 Jan	16243418
Primary steps of the photochemical reactions of 2-cyano-10-(3-[dimethylamino, N-oxide]-2-methylpropyl)-5-oxide-phenothiazine, the photoproduct of cyamemazine, a phototoxic neuroleptic: comparison with the sulfoxide.	2006 Mar	16520870
Characterization of human cytochrome P450 enzymes involved in the metabolism of cyamemazine.	2007 Dec	17951033
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.	2007 Jun	17333501
[Acute Datura stramonium poisoning in an emergency department].	2007 Oct	17560071
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	19102734
[Treatment of a serious autistic disorder in a child with Naltrexone in an oral suspension form].	2009 Apr	19393386
[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals].	2009 Apr	19393381
Antipsychotics-induced ischaemic colitis and gastrointestinal necrosis: a review of the French pharmacovigilance database.	2009 Oct	19572384
Effect of cyamemazine on the steady-state plasma concentrations of risperidone and 9-hydroxyrisperidone: a preliminary retrospective study.	2010 Dec	21068648
A tendency for re-offending in drug-facilitated crime.	2010 Mar 20	20116946
Buprenorphine-related deaths: unusual forensic situations.	2010 Nov	20369247

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 25-600 mg daily in 2 or 3 divided doses with larger doses taken at night. Intramuscular: 25-200 mg daily.

Route of Administration: Other

In Vitro Use Guide

Binding to receptors was carried out using radioligand binding assay. Suspension of cells, expressing the receptor was incubated with cyamemazine and a reference radioligand. At the end of incubation period, membranes or cells were rapidly filtered under vacuum conditions through glass fiber filters. Bound radioactivity was measured with a scintillation counter. Each competition concentration-response curve was determined in duplicated using cyamemazine concentration spanning from 0.03 nM to 30-100 uM

Name

Type

Language

CYAMEMAZINE TARTRATE

Common Name

English

10-(3-DIMETHYLAMINO-2-METHYLPROPYL)PHENOTHIAZINE-2-CARBONITRILE TARTRATE

Systematic Name

English

10H-PHENOTHIAZINE-2-CARBONITRILE, 10-(3-(DIMETHYLAMINO)-2-METHYLPROPYL)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

Cyamemazine tartrate [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

24892868