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
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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P21728 Gene ID: 1812.0 Gene Symbol: DRD1 Target Organism: Homo sapiens (Human) |
3.8 nM [Ki] | ||
Target ID: CHEMBL234 |
2.5 nM [Ki] | ||
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) |
1.5 nM [Ki] | ||
Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) |
12.0 nM [Ki] | ||
Target ID: CHEMBL2095203 |
2.3 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TERCIAN Approved UseChronic psychotic states (schizophrenia, chronic non-schizophrenic delusions: paranoid delusions, chronic hallucinatory psychoses). |
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| Primary | TERCIAN Approved UseShort-term symptomatic treatment of adult anxiety in case of failure of usual therapies. |
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| Primary | TERCIAN Approved UseIn combination with an antidepressant, short-term treatment of some severe forms of major depressive episode. |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hypertonia and malignant hyperthermia due to morphine and neuroleptic. | 1981 Feb 14 |
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| Transient ST segment elevation in right precordial leads induced by psychotropic drugs: relationship to the Brugada syndrome. | 2001 Jan |
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| Concentrations of cis(Z)-clopenthixol and trans(E)-clopenthixol in a lethal case involving zuclopenthixol, diazepam, and cyamemazine. | 2001 Jul-Aug |
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| Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice. | 2001 Sep 28 |
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| [Pharmaco-epidemiological study on antipsychotic drug prescription in French Psychiatry: Patient characteristics, antipsychotic treatment, and care management for schizophrenia]. | 2002 Mar-Apr |
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| 5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle. | 2002 Nov 15 |
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| A randomised, double-blind comparison of milnacipran and imipramine in the treatment of depression. | 2002 Oct |
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| Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine. | 2003 Feb |
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| Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes. | 2003 Feb 1 |
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| [Catatonia de novo, report on a case: immediate vital prognosis and psychiatric prognosis in longer term]. | 2003 Jan-Feb |
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| Acute fatal poisoning with cyamemazine. | 2003 Oct 14 |
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| Interspecies variability and drug interactions of loxapine metabolism in liver microsomes. | 2003 Oct-Dec |
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| Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome. | 2004 Fall |
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| An insight into the mechanisms of the phototoxic response induced by cyamemazine in cultured fibroblasts and keratinocytes. | 2004 Feb |
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| Primary photochemical processes of the phototoxic neuroleptic cyamemazine: a study by laser flash photolysis and steady-state irradiation. | 2004 Nov-Dec |
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| A positron emission tomography (PET) study of cerebral dopamine D2 and serotonine 5-HT2A receptor occupancy in patients treated with cyamemazine (Tercian). | 2005 Jul |
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| Contrasting action of flavonoids on phototoxic effects induced in human skin fibroblasts by UVA alone or UVA plus cyamemazine, a phototoxic neuroleptic. | 2005 May |
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| 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 |
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| Double-blind study of cyamemazine and diazepam in the alcohol withdrawal syndrome. | 2005 Oct |
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| Effects of cyamemazine on hERG, INa, ICa, Ito, Isus and IK1 channel currents, and on the QTc interval in guinea pigs. | 2006 Feb 27 |
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| Double-blind, comparative study of cyamemazine vs. bromazepam in the benzodiazepine withdrawal syndrome. | 2006 Jan |
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| 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 |
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| Characterization of human cytochrome P450 enzymes involved in the metabolism of cyamemazine. | 2007 Dec |
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| Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study. | 2007 Jun |
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| [Acute Datura stramonium poisoning in an emergency department]. | 2007 Oct |
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| Fatal intoxication with milnacipran. | 2008 Aug |
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| 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 |
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| Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes. | 2008 Jan 14 |
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| Cyamemazine metabolites: effects on human cardiac ion channels in-vitro and on the QTc interval in guinea pigs. | 2008 Nov |
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| [Treatment of a serious autistic disorder in a child with Naltrexone in an oral suspension form]. | 2009 Apr |
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| [Prescribing patterns of antipsychotics in 13 French psychiatric hospitals]. | 2009 Apr |
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| 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 |
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| A tendency for re-offending in drug-facilitated crime. | 2010 Mar 20 |
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| 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
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24892868
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93841-82-8
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236251
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100000088201
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C4ZT3BE459
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SUB01510MIG
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DTXSID70917530
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ACTIVE MOIETY
SUBSTANCE RECORD
