U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H21N3S
Molecular Weight 323.4569
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYAMEMAZINE

SMILES

CC(CN(C)C)CN1c2ccccc2Sc3ccc(cc31)C#N

InChI

InChIKey=SLFGIOIONGJGRT-UHFFFAOYSA-N
InChI=1S/C19H21N3S/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/h4-10,14H,12-13H2,1-3H3

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21728
Gene ID: 1812
Gene Symbol: DRD1
Target Organism: Homo sapiens (Human)
3.79999999999999982 nM [Ki]
2.5 nM [Ki]
Target ID: P28223
Gene ID: 3356
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
1.5 nM [Ki]
Target ID: P28335
Gene ID: 3358
Gene Symbol: HTR2C
Target Organism: Homo sapiens (Human)
12 nM [Ki]
2.29999999999999982 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TERCIAN

Approved Use

Chronic psychotic states (schizophrenia, chronic non-schizophrenic delusions: paranoid delusions, chronic hallucinatory psychoses).
Primary
TERCIAN

Approved Use

Short-term symptomatic treatment of adult anxiety in case of failure of usual therapies.
Primary
TERCIAN

Approved Use

In combination with an antidepressant, short-term treatment of some severe forms of major depressive episode.
Primary
PubMed

PubMed

TitleDatePubMed
Hypertonia and malignant hyperthermia due to morphine and neuroleptic.
1981 Feb 14
Transient ST segment elevation in right precordial leads induced by psychotropic drugs: relationship to the Brugada syndrome.
2001 Jan
Concentrations of cis(Z)-clopenthixol and trans(E)-clopenthixol in a lethal case involving zuclopenthixol, diazepam, and cyamemazine.
2001 Jul-Aug
Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice.
2001 Sep 28
[Pharmaco-epidemiological study on antipsychotic drug prescription in French Psychiatry: Patient characteristics, antipsychotic treatment, and care management for schizophrenia].
2002 Mar-Apr
5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle.
2002 Nov 15
A randomised, double-blind comparison of milnacipran and imipramine in the treatment of depression.
2002 Oct
Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine.
2003 Feb
Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes.
2003 Feb 1
[Catatonia de novo, report on a case: immediate vital prognosis and psychiatric prognosis in longer term].
2003 Jan-Feb
Acute fatal poisoning with cyamemazine.
2003 Oct 14
Interspecies variability and drug interactions of loxapine metabolism in liver microsomes.
2003 Oct-Dec
Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome.
2004 Fall
An insight into the mechanisms of the phototoxic response induced by cyamemazine in cultured fibroblasts and keratinocytes.
2004 Feb
Primary photochemical processes of the phototoxic neuroleptic cyamemazine: a study by laser flash photolysis and steady-state irradiation.
2004 Nov-Dec
A positron emission tomography (PET) study of cerebral dopamine D2 and serotonine 5-HT2A receptor occupancy in patients treated with cyamemazine (Tercian).
2005 Jul
Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic.
2005 May
False-positive results in the detection of methadone in urines of patients treated with psychotropic substances.
2005 Nov
[Alcohol dependence and depressive disorders in the course of opiate dependence].
2005 Oct
Double-blind study of cyamemazine and diazepam in the alcohol withdrawal syndrome.
2005 Oct
Effects of cyamemazine on hERG, INa, ICa, Ito, Isus and IK1 channel currents, and on the QTc interval in guinea pigs.
2006 Feb 27
Double-blind, comparative study of cyamemazine vs. bromazepam in the benzodiazepine withdrawal syndrome.
2006 Jan
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
Characterization of human cytochrome P450 enzymes involved in the metabolism of cyamemazine.
2007 Dec
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
[Acute Datura stramonium poisoning in an emergency department].
2007 Oct
Fatal intoxication with milnacipran.
2008 Aug
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
Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes.
2008 Jan 14
Cyamemazine metabolites: effects on human cardiac ion channels in-vitro and on the QTc interval in guinea pigs.
2008 Nov
[Treatment of a serious autistic disorder in a child with Naltrexone in an oral suspension form].
2009 Apr
[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals].
2009 Apr
Antipsychotics-induced ischaemic colitis and gastrointestinal necrosis: a review of the French pharmacovigilance database.
2009 Oct
Effect of cyamemazine on the steady-state plasma concentrations of risperidone and 9-hydroxyrisperidone: a preliminary retrospective study.
2010 Dec
A tendency for re-offending in drug-facilitated crime.
2010 Mar 20
Buprenorphine-related deaths: unusual forensic situations.
2010 Nov
Patents

Sample Use Guides

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
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
INN   MART.   MI   WHO-DD  
INN  
Official Name English
TH-2602
Code English
FL-6229
Code English
TERCIAN
Brand Name English
CYAMEMAZINE [MI]
Common Name English
RP-7204
Code English
RP 7204
Code English
10-(3-(DIMETHYLAMINO)-2-METHYLPROPYL)PHENOTHIAZINE-2-CARBONITRILE
Systematic Name English
CYAMEMAZINE [WHO-DD]
Common Name English
CYAMEMAZINE [INN]
Common Name English
CYAMEMAZINE [MART.]
Common Name English
CYAMEPROMAZINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
WHO-VATC QN05AA06
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
WHO-ATC N05AA06
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
Code System Code Type Description
DRUG CENTRAL
746
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
RXCUI
21877
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB09000
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
NCI_THESAURUS
C79120
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
MERCK INDEX
M3943
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
222-594-2
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
EVMPD
SUB06836MIG
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
PUBCHEM
62865
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
WIKIPEDIA
Cyamemazine
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL2104153
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
MESH
C028457
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
FDA UNII
A2JGV5CNU4
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
CAS
3546-03-0
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY
INN
1148
Created by admin on Sat Jun 26 03:19:56 UTC 2021 , Edited by admin on Sat Jun 26 03:19:56 UTC 2021
PRIMARY