Cyamemazine
(Synonyms: 氰美马嗪) 目录号 : GC38760
Cyamemazine 是一种抗精神病药，其中含有吩噻嗪发色团，通常被用作抗焦虑药。Cyamemazine 是具有抗精神病活性的有效的 5-HT3 (Ki 为 12 nM), 5-HT2A (Ki 为 1.5 nM) 和 5-HT2C (Ki 为 75 nM) 受体拮抗剂。
Cas No.:3546-03-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
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- Datasheet
Cyamemazine is a neuroleptic agent that contains the phenothiazine chromophore. Cyamemazine is often used as an anxiolytic. Cyamemazine is a potent 5-HT3 (Ki of 12 nM), 5-HT2A (Ki = 1.5 nM) and 5-HT2C (Ki of 75 nM) receptors antagonist with antipsychotic activity[1][2].
Cyamemazine exhibits a high affinity for dopamine receptors, which is consistent with its antipsychotic activity. The antagonist activity of Cyamemazine at muscarinic receptors is consistent with its affinity for M1 (Ki = 13 nM), M2 (Ki = 42 nM), M3 (Ki = 321 nM), M4 (Ki = 12 nM), and M5 (Ki = 35 nM) receptors[1].
Cyamemazine behaves as an antagonist at the 5-HT3, 5-HT2C, and 5-HT2A receptors in 5-HT3-dependent contraction of isolated guinea pig ileum and bradycardic responses in rats, in 5-HT2C-dependent phospholipase C stimulation in the rat brain membrane, and in 5-HT2A-dependent contraction of isolated rat aorta rings and isolated guinea pig trachea. Cyamemazine antagonizes 5-HT3 and 5-HT2C receptors and that this effect is partially involved in its therapeutic activity in anxiety disorders. Acute administration of low doses of Cyamemazine can reduces extracellular dopamine and metabolite concentrations in rat striatum[1].
[1]. Bourin M, et al. Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome. CNS Drug Rev. 2004 Fall;10(3):219-29. [2]. Vendrell-Criado V, et al. Photobehavior of the antipsychotic drug cyamemazine in a supramolecular gel protective environment. J Photochem Photobiol B. 2020 Jan;202:111686.
| Cas No. | 3546-03-0 | SDF | |
| 别名 | 氰美马嗪 | ||
| Canonical SMILES | CN(C)CC(C)CN1C2=C(C=CC(C#N)=C2)SC3=CC=CC=C31 | ||
| 分子式 | C19H21N3S | 分子量 | 323.46 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0916 mL | 15.4579 mL | 30.9157 mL |
| 5 mM | 0.6183 mL | 3.0916 mL | 6.1831 mL |
| 10 mM | 0.3092 mL | 1.5458 mL | 3.0916 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
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计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
[Therapeutic drug monitoring of Cyamemazine: How to interpret a concentration? A review of literature]
Therapie 2022 Sep-Oct;77(5):603-609.PMID:35221129DOI:10.1016/j.therap.2022.01.018.
Cyamemazine is the most prescribed antipsychotic drug in France, often in combination with another antipsychotic, for its sedative and anxiolytic component. Providing to physicians serum concentrations of Cyamemazine in different contexts (compliance checking, ineffectiveness, adverse effects, intoxication, modification of pharmacokinetic parameters…) requires to interpret them correctly. This article presents an update on how to interpret a concentration of Cyamemazine, wich remains poorly documented. The anxiolysis occurs at steady-state serum trough concentrations of 4 to 5μg/L; the antipsychotic effect from 18-20μg/L. Cyamemazine is not a drug with a narrow therapeutic window and concentrations up to 400μg/L may be sought in cases of partial efficacy; concentrations of 1800μg/L might be fatal; lower concentrations might be fatal if association with high others concentrations of drugs.
Preclinical and clinical pharmacology of Cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome
CNS Drug Rev 2004 Fall;10(3):219-29.PMID:15492772DOI:10.1111/j.1527-3458.2004.tb00023.x.
Several studies have suggested that the antipsychotic compound, Cyamemazine, possesses anxiolytic properties in humans. The original pharmacological profile of Cyamemazine (D(2), 5-HT(2A), 5-HT(2C), and 5-HT(3) receptor antagonist), which was established by binding, microdialysis and behavioral studies, is consistent with these observations. In the light/dark exploration test, Cyamemazine demonstrated anxiolytic-like activity by acute, but not chronic administration. By chronic administration, however, Cyamemazine increased the time spent in the open arms of the elevated plus maze (EPM) test demonstrating anxiolytic-like activity. The discrepancy between the results obtained in these tests by acute and chronic administration, could be due to a combination of dopamine D(2) receptor antagonism with antagonism of the 5-HT(2C) and 5-HT(3) receptors. The action of Cyamemazine on both the dopaminergic system and 5-HT(3) receptors could also explain the activity of Cyamemazine in the management of alcohol withdrawal demonstrated in preclinical studies. This potential indication for Cyamemazine and its activity in benzodiazepine withdrawal syndrome have recently been investigated in clinical trials and the results of these studies are presented in this review.
Potential role of cortical 5-HT(2A) receptors in the anxiolytic action of Cyamemazine in benzodiazepine withdrawal
Psychiatry Res 2012 Jul 30;198(2):307-12.PMID:22421069DOI:10.1016/j.psychres.2012.01.009.
The antipsychotic Cyamemazine is a potent serotonin 5-HT(2A) receptor (5-HT(2AR)) antagonist. A positron emission tomography (PET) study in human patients showed that therapeutic doses of Cyamemazine produced near saturation of 5-HT(2AR) occupancy in the frontal cortex, whereas dopamine D(2) occupancy remained below the level for motor side effects observed with typical antipsychotics. Recently, numerous studies have revealed the involvement of 5-HT(2AR) in the pathophysiology of anxiety and a double-blind, randomized clinical trial showed similar efficacy of Cyamemazine and bromazepam in reducing the anxiety associated with benzodiazepine withdrawal. Therefore, we reviewed the above articles about 5-HT(2AR) and anxiety in order to understand better the anxiolytic mechanisms of Cyamemazine in benzodiazepine withdrawal. The 5-HT(2AR) is the most abundant serotonin receptor subtype in the cortex. Non-pharmacological studies with antisense oligodeoxynucleotides and genetically modified mice clearly showed that cortical 5-HT(2AR) signaling positively modulates anxiety-like behavior. With a few exceptions, most other studies reviewed here further support this view. Therefore, the anxiolytic efficacy of Cyamemazine in benzodiazepine withdrawal can be due to a 5-HT(2AR) antagonistic activity at the cortical level.
Pharmacological interventions for benzodiazepine discontinuation in chronic benzodiazepine users
Cochrane Database Syst Rev 2018 Mar 15;3(3):CD011481.PMID:29543325DOI:10.1002/14651858.CD011481.pub2.
Background: Prolonged treatment with benzodiazepines is common practice despite clinical recommendations of short-term use. Benzodiazepines are used by approximately 4% of the general population, with increased prevalence in psychiatric populations and the elderly. After long-term use it is often difficult to discontinue benzodiazepines due to psychological and physiological dependence. This review investigated if pharmacological interventions can facilitate benzodiazepine tapering. Objectives: To assess the benefits and harms of pharmacological interventions to facilitate discontinuation of chronic benzodiazepine use. Search methods: We searched the following electronic databases up to October 2017: Cochrane Drugs and Alcohol Group's Specialised Register of Trials, CENTRAL, PubMed, Embase, CINAHL, and ISI Web of Science. We also searched ClinicalTrials.gov, the WHO ICTRP, and ISRCTN registry, and checked the reference lists of included studies for further references to relevant randomised controlled trials. Selection criteria: We included randomised controlled trials comparing pharmacological treatment versus placebo or no intervention or versus another pharmacological intervention in adults who had been treated with benzodiazepines for at least two months and/or fulfilled criteria for benzodiazepine dependence (any criteria). Data collection and analysis: We used standard methodological procedures expected by Cochrane. Main results: We included 38 trials (involving 2543 participants), but we could only extract data from 35 trials with 2295 participants. Many different interventions were studied, and no single intervention was assessed in more than four trials. We extracted data on 18 different comparisons. The risk of bias was high in all trials but one. Trial Sequential Analysis showed imprecision for all comparisons.For benzodiazepine discontinuation, we found a potential benefit of valproate at end of intervention (1 study, 27 participants; risk ratio (RR) 2.55, 95% confidence interval (CI) 1.08 to 6.03; very low-quality evidence) and of tricyclic antidepressants at longest follow-up (1 study, 47 participants; RR 2.20, 95% CI 1.27 to 3.82; low-quality evidence).We found potentially positive effects on benzodiazepine withdrawal symptoms of pregabalin (1 study, 106 participants; mean difference (MD) -3.10 points, 95% CI -3.51 to -2.69; very low-quality evidence), captodiame (1 study, 81 participants; MD -1.00 points, 95% CI -1.13 to -0.87; very low-quality evidence), paroxetine (2 studies, 99 participants; MD -3.57 points, 95% CI -5.34 to -1.80; very low-quality evidence), tricyclic antidepressants (1 study, 38 participants; MD -19.78 points, 95% CI -20.25 to -19.31; very low-quality evidence), and flumazenil (3 studies, 58 participants; standardised mean difference -0.95, 95% CI -1.71 to -0.19; very low-quality evidence) at end of intervention. However, the positive effect of paroxetine on benzodiazepine withdrawal symptoms did not persist until longest follow-up (1 study, 54 participants; MD -0.13 points, 95% CI -4.03 to 3.77; very low-quality evidence).The following pharmacological interventions reduced symptoms of anxiety at end of intervention: carbamazepine (1 study, 36 participants; MD -6.00 points, 95% CI -9.58 to -2.42; very low-quality evidence), pregabalin (1 study, 106 participants; MD -4.80 points, 95% CI -5.28 to -4.32; very low-quality evidence), captodiame (1 study, 81 participants; MD -5.70 points, 95% CI -6.05 to -5.35; very low-quality evidence), paroxetine (2 studies, 99 participants; MD -6.75 points, 95% CI -9.64 to -3.86; very low-quality evidence), and flumazenil (1 study, 18 participants; MD -1.30 points, 95% CI -2.28 to -0.32; very low-quality evidence).Two pharmacological treatments seemed to reduce the proportion of participants that relapsed to benzodiazepine use: valproate (1 study, 27 participants; RR 0.31, 95% CI 0.11 to 0.90; very low-quality evidence) and Cyamemazine (1 study, 124 participants; RR 0.33, 95% CI 0.14 to 0.78; very low-quality evidence). Alpidem decreased the proportion of participants with benzodiazepine discontinuation (1 study, 25 participants; RR 0.41, 95% CI 0.17 to 0.99; number needed to treat for an additional harmful outcome (NNTH) 2.3 participants; low-quality evidence) and increased the occurrence of withdrawal syndrome (1 study, 145 participants; RR 4.86, 95% CI 1.12 to 21.14; NNTH 5.9 participants; low-quality evidence). Likewise, magnesium aspartate decreased the proportion of participants discontinuing benzodiazepines (1 study, 144 participants; RR 0.80, 95% CI 0.66 to 0.96; NNTH 5.8; very low-quality evidence).Generally, adverse events were insufficiently reported. Specifically, one of the flumazenil trials was discontinued due to severe panic reactions. Authors' conclusions: Given the low or very low quality of the evidence for the reported outcomes, and the small number of trials identified with a limited number of participants for each comparison, it is not possible to draw firm conclusions regarding pharmacological interventions to facilitate benzodiazepine discontinuation in chronic benzodiazepine users. Due to poor reporting, adverse events could not be reliably assessed across trials. More randomised controlled trials are required with less risk of systematic errors ('bias') and of random errors ('play of chance') and better and full reporting of patient-centred and long-term clinical outcomes. Such trials ought to be conducted independently of industry involvement.
[Cyamemazine (Tercian®): Exploration of extrapyramidal syndrome cases contained in the French pharmacovigilance database]
Therapie 2017 Jun;72(3):345-350.PMID:27726885DOI:10.1016/j.therap.2016.07.004.
Purpose: Cyamemazine (Tercian®) is currently the most widely prescribed neuroleptic in France. This widespread use is due to its anxiolytics properties and to a claimed good safety profile. Although, prescription of Cyamemazine is not devoid of the risks associated with the use of neuroleptics: extrapyramidal syndromes. This study aims at describing extrapyramidal syndromes induced by Cyamemazine registered in the French pharmacovigilance database. Methods: All spontaneous reports of extrapyramidal syndromes in the French pharmacovigilance database between 1st January 1985 and 31th December 2015 were described and analyzed. Results: During this period 132 cases following Cyamemazine intake were reported in the French pharmacovigilance database. The extrapyramidal syndromes were considered as "serious" in 77% of cases. More than 80% of the cases were described with a dosage of Cyamemazine under 100mg/day and no correlation between drug dose and seriousness of the cases were found. Thirty-six cases were described with a monotherapy of Cyamemazine. Conclusion: We should keep in mind that despite its widespread use in various indications (e.g. anxiolytic) Cyamemazine remains a neuroleptic and could induce extrapyramidal syndromes even with low dosage. Careful monitoring should be performed when introducing and with long-term use of Cyamemazine, mostly in elderly patients or patient already being treated with neuroleptics.