CYAMEMAZINE TARTRATE

Possibly Marketed Outside US

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=C1C=C(C=C3)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 2849	3.8 nM [Ki]
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2849	2.5 nM [Ki]
5-hydroxytryptamine receptor 2A 73 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 2849	1.5 nM [Ki]
5-hydroxytryptamine receptor 2C 29 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 2849	12.0 nM [Ki]
Adrenergic receptor alpha 65 Target ID: CHEMBL2095203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527336	Antagonist 2849	2.3 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492772	Primary	Approved 8583	TERCIAN Approved Use Chronic psychotic states (schizophrenia, chronic non-schizophrenic delusions: paranoid delusions, chronic hallucinatory psychoses).
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15492772	Primary	Approved 8583	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 8583	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 511	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/15492772/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		CYAMEMAZINE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.99 h REVIEW https://pubmed.ncbi.nlm.nih.gov/15492772/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		CYAMEMAZINE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
120 mg 1 times / day steady-state, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: steady-state Dose: 120 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23473285/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23473285/	Disc. AE: Photoallergic reaction... AEs leading to discontinuation/dose reduction: Photoallergic reaction (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/23473285/
50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/	Disc. AE: Epilepsy, Anxiety... AEs leading to discontinuation/dose reduction: Epilepsy (1 pt) Anxiety (1 pt) Hepatic failure (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/
50 mg 1 times / day steady-state, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady-state Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/	Other AEs: Anxiety, Insomnia... Other AEs: Anxiety (5 patients) Insomnia (6 patients) Dry mouth (6 patients) Somnolence (8 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/

AEs

AE	Significance	Dose	Population
Photoallergic reaction	1 pt Disc. AE	120 mg 1 times / day steady-state, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: steady-state Dose: 120 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23473285/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23473285/
Anxiety	1 pt Disc. AE	50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/
Epilepsy	1 pt Disc. AE	50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/
Hepatic failure	1 pt Disc. AE	50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16118830/
Anxiety	5 patients	50 mg 1 times / day steady-state, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady-state Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/
Dry mouth	6 patients	50 mg 1 times / day steady-state, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady-state Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/
Insomnia	6 patients	50 mg 1 times / day steady-state, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady-state Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/
Somnolence	8 patients	50 mg 1 times / day steady-state, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady-state Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16243418/

PubMed

Title	Date	PubMed
Effect of cyamemazine on the steady-state plasma concentrations of risperidone and 9-hydroxyrisperidone: a preliminary retrospective study.	2010-12	21068648
Buprenorphine-related deaths: unusual forensic situations.	2010-11	20369247
A tendency for re-offending in drug-facilitated crime.	2010-03-20	20116946
Antipsychotics-induced ischaemic colitis and gastrointestinal necrosis: a review of the French pharmacovigilance database.	2009-10	19572384
[Treatment of a serious autistic disorder in a child with Naltrexone in an oral suspension form].	2009-04	19393386
[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals].	2009-04	19393381
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).	2008-12-22	19102734
Cyamemazine metabolites: effects on human cardiac ion channels in-vitro and on the QTc interval in guinea pigs.	2008-11	18957172
Fatal intoxication with milnacipran.	2008-08	18586210
Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes.	2008-01-14	17936750
Characterization of human cytochrome P450 enzymes involved in the metabolism of cyamemazine.	2007-12	17951033
[Acute Datura stramonium poisoning in an emergency department].	2007-10	17560071
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.	2007-06	17333501
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.	2006-03	16520870
Effects of cyamemazine on hERG, INa, ICa, Ito, Isus and IK1 channel currents, and on the QTc interval in guinea pigs.	2006-02-27	16494862
Double-blind, comparative study of cyamemazine vs. bromazepam in the benzodiazepine withdrawal syndrome.	2006-01	16243418
False-positive results in the detection of methadone in urines of patients treated with psychotropic substances.	2005-11	16244295
[Alcohol dependence and depressive disorders in the course of opiate dependence].	2005-10	16673707
Double-blind study of cyamemazine and diazepam in the alcohol withdrawal syndrome.	2005-10	16118830
A positron emission tomography (PET) study of cerebral dopamine D2 and serotonine 5-HT2A receptor occupancy in patients treated with cyamemazine (Tercian).	2005-07	15948013
Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic.	2005-05	15875075
Primary photochemical processes of the phototoxic neuroleptic cyamemazine: a study by laser flash photolysis and steady-state irradiation.	2004-12-30	15623341
An insight into the mechanisms of the phototoxic response induced by cyamemazine in cultured fibroblasts and keratinocytes.	2004-02	15068029
Interspecies variability and drug interactions of loxapine metabolism in liver microsomes.	2004-01-28	14743971
Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome.	2004	15492772
Acute fatal poisoning with cyamemazine.	2003-10-14	14550607
[Catatonia de novo, report on a case: immediate vital prognosis and psychiatric prognosis in longer term].	2003-03-18	12640330
Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes.	2003-02-01	12527336
Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine.	2003-02	12595954
5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle.	2002-11-15	12421652
A randomised, double-blind comparison of milnacipran and imipramine in the treatment of depression.	2002-10	12204314
[Pharmaco-epidemiological study on antipsychotic drug prescription in French Psychiatry: Patient characteristics, antipsychotic treatment, and care management for schizophrenia].	2002-04-25	11972139
Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice.	2001-09-28	11423169
Concentrations of cis(Z)-clopenthixol and trans(E)-clopenthixol in a lethal case involving zuclopenthixol, diazepam, and cyamemazine.	2001-08-14	11499890
Transient ST segment elevation in right precordial leads induced by psychotropic drugs: relationship to the Brugada syndrome.	2001-01	11204086
Hypertonia and malignant hyperthermia due to morphine and neuroleptic.	1981-02-14	6110016

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 `Mon Mar 31 21:23:05 GMT 2025` Edited by `admin` on `Mon Mar 31 21:23:05 GMT 2025`
Record UNII	C4ZT3BE459
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

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

Preferred Name

English

CYAMEMAZINE TARTRATE

Common 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