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

Molecular Formula	C19H21N3S
Molecular Weight	323.455
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle.	2002 Nov 15	12421652
A randomised, double-blind comparison of milnacipran and imipramine in the treatment of depression.	2002 Oct	12204314
[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
Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome.	2004 Fall	15492772
Primary photochemical processes of the phototoxic neuroleptic cyamemazine: a study by laser flash photolysis and steady-state irradiation.	2004 Nov-Dec	15623341
False-positive results in the detection of methadone in urines of patients treated with psychotropic substances.	2005 Nov	16244295
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
Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes.	2008 Jan 14	17936750
[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
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:40:33 UTC 2023` Edited by `admin` on `Sat Dec 16 04:40:33 UTC 2023`
Record UNII	C4ZT3BE459
Record Status	`Validated (UNII)`
Record Version

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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