CAS: 111974-69-7; Quetiapine

英文名称Quetiapine
中文名称喹硫平
IUPAC名称2-(2-(4-dibenzo[b,f][1,4]thiazepine- 11-yl- 1-piperazinyl)ethoxy)ethanol
其它别名2-[2-(4-Dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol
CAS编号111974-69-7
MFCD编号:MFCD08064204
EINECS号:601-143-7
FDA UNII编号:BGL0JSY5SI
分子式:C21H25N3O2S
分子量:383.51
产品CID: 154312
同类组份化合物CAS111974-72-2 (hemifumarate)111974-69-7 (free base)
产品分类原料药 → 神经系统用药 → 抗精神病药

相似结构搜索
产品信息参考
InChIKey: URKOMYMAXPYINW-UHFFFAOYSA-N
InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2…
计算化学: 氢键受体数5.0氢键供体数1.0可旋转键数6.0

物理性质

熔点172 - 174 °C
沸点556.5±60.0 °C at 760 mmHg
闪点290.4±32.9 °C
密度1.3±0.1 g/cm3
pKa:14.41±0.10(预测)
PSA:73.6
LogP:1.57
折射率1.653
蒸汽压0.0±1.6 mmHg at 25°C
溶解性H2O: < 0.1 mg/mL (Insoluble)
外观形态淡黄色至黄色粉末
储存条件储存在 -20°C
产品应用奎硫平(111974-69-7)的用途:该药是吩噻嗪类抗精神病药.用于各型精神分裂症.本品不仅对精神分裂症阳性症状有效,对阴性症状也有一定效果.也可以减轻与精神分裂症有关的情感症状如抑郁,焦虑及认知缺陷症状.

MSDS等安全信息

GHS象形图
GHS符号GHS07 & GHS05 & GHS09;
注释: Exclamation mark & Corrosion & Environment
危险类别急性毒性类别4(经口)
严重眼损伤类别1
水生慢性毒性类别1
特定目标器官毒性 - 单次接触类别3
水生慢性毒性类别3
警示词Danger(危险)
危险描述H302 |吞咽有害.
H318 |造成严重眼损伤.
H410 |对水生生物毒性极大并具有长期持续影响.
H335 |可能引起呼吸道刺激.
H412 |对水生生物有害并具有长期持续影响.
防范说明P280-P305+P351+P338-P310-P264-P270-P301+P312-P330-P501-P273-P391-P501
UN编号HAZARD
危险品标志T,F
安全声明IDENTIFICATION AND USE: Quetiapine fumarate is used for the symptomatic management of psychotic disorders. Short-term efficacy of quetiapine for the management of schizophrenia has been established by placebo-controlled studies of 6 weeks' duration principally in hospitalized patients with schizophrenia. Quetiapine is used alone or in conjunction with lithium or divalproex sodium for the management of acute manic episodes associated with bipolar I disorder. Quetiapine also is used for the treatment of depressive episodes associated with bipolar disorder. HUMAN EXPOSURE AND TOXICITY: The most common adverse effects reported in 5% or more of patients receiving quetiapine therapy for schizophrenia or bipolar disorder and at a frequency twice that reported among patients receiving placebo in clinical trials include somnolence, sedation, asthenia, lethargy, dizziness, dry mouth, constipation, increased ALT, weight gain, dyspepsia, abdominal pain, postural hypotension, and pharyngitis. The development of cataracts in association with quetiapine was observed in animal studies. Lens changes also have been reported in some patients receiving long-term quetiapine therapy, although a causal relationship has not been established. Seizures occurred in 0.6% of patients receiving quetiapine in controlled clinical trials. Geriatric patients with dementia-related psychosis treated with atypical antipsychotic drugs appear to be at an increased risk of death compared with that among patients receiving placebo. Worsening of depression and/or the emergence of suicidal ideation and behavior (suicidality) or unusual changes in behavior may occur in both adult and pediatric patients with major depressive disorder and other psychiatric disorders, whether or not they are taking antidepressants. Neuroleptic malignant syndrome (NMS), a potentially fatal syndrome requiring immediate discontinuance of the drug and intensive symptomatic treatment, has been reported in patients receiving antipsychotic agents, including quetiapine. Contact dermatitis, maculopapular rash, and photosensitivity reactions were reported infrequently during clinical trials. Anaphylaxis and Stevens-Johnson syndrome have been reported during postmarketing surveillance. Quetiapine appears to be distributed into human milk in relatively small amounts. The effect of quetiapine on labor and delivery is unknown. Safety and efficacy of quetiapine in pediatric patients younger than 18 years of age with bipolar depression have not been established. Quetiapine overdose causes central nervous system depression and sinus tachycardia. In large overdoses, patients may require intubation and ventilation for associated respiratory depression. Although a prolonged QTc occurs, its clinical significance is unclear because it is most likely caused by an overcorrection caused by the tachycardia. No evidence of clastogenic potential was obtained in an in vitro chromosomal aberration assay in cultured human lymphocytes. ANIMAL STUDIES: Quetiapine caused a dose-related increase in pigment deposition in thyroid gland in a mouse 2 year carcinogenicity study. Doses were 75-750 mg/kg. The identity of the pigment could not be determined, but was found to be co-localized with quetiapine in thyroid gland follicular epithelial cells. The functional effects and the relevance of this finding to human risk are unknown. In dogs receiving quetiapine for 6 or 12 months, but not for 1 month, focal triangular cataracts occurred at the junction of posterior sutures in the outer cortex of the lens at a dose of 100 mg/kg. This finding may be due to inhibition of cholesterol biosynthesis by quetiapine. Quetiapine caused a dose related reduction in plasma cholesterol levels in repeat-dose dog and monkey studies; however, there was no correlation between plasma cholesterol and the presence of cataracts in individual dogs. The appearance of delta-8-cholestanol in plasma is consistent with inhibition of a late stage in cholesterol biosynthesis in these species. There also was a 25% reduction in cholesterol content of the outer cortex of the lens observed in a special study in quetiapine treated female dogs. The teratogenic potential of quetiapine was studied in rats and rabbits dosed during the period of organogenesis. No evidence of a teratogenic effect was detected in rats at doses of 25 to 200 mg/kg or in rabbits at 25 to 100 mg/kg. There was, however, evidence of embryo/fetal toxicity. Delays in skeletal ossification were detected in rat fetuses at doses of 50 and 200 mg/ kg and in rabbits at 50 and 100 mg/kg. Fetal body weight was reduced in rat fetuses at 200 mg/kg and rabbit fetuses at 100 mg/kg. There was an increased incidence of a minor soft tissue anomaly (carpal/tarsal flexure) in rabbit fetuses at a dose of 100 mg/kg. Evidence of maternal toxicity (i.e., decreases in body weight gain and/or death) was observed at the high dose in the rat study and at all doses in the rabbit study. In a peri/ postnatal reproductive study in rats, no drug-related effects were observed at doses of 1, 10, and 20 mg/kg. However, in a preliminary peri/postnatal study, there were increases in fetal and pup death, and decreases in mean litter weight at 150 mg/kg. The mutagenic potential of quetiapine was tested in six in vitro bacterial gene mutation assays and in an in vitro mammalian gene mutation assay in Chinese Hamster Ovary cells. However, sufficiently high concentrations of quetiapine may not have been used for all tester strains. Quetiapine did produce a reproducible increase in mutations in one Salmonella typhimurium tester strain in the presence of metabolic activation. No evidence of clastogenic potential was obtained in the in vivo micronucleus assay in rats. | Quetiapine can be life-threatening if abused or misused. Toxicity is associated with levels greater than 1500 ng/mL in serum or plasma. Supportive care is the mainstay of treatment. In acute toxicity, measures are necessary to maintain the airway and ensure adequate oxygenation and ventilation. Gastric lavage and activated charcoal administration alongside a laxative to prevent further drug absorption are used if time appropriate. Plasma concentrations of quetiapine reach maximal levels within 1 to 2 hours of oral administration. ECG is a recommendation to monitor for possible Torsades de pointes or another arrhythmia due to QT-interval prolongation. Treat extrapyramidal effects with anticholinergic and hypotension with intravenous fluids and sympathomimetic agents such as A1 agonists. Management/treatment of neuroleptic malignant syndrome is possible by immediate withdrawal of quetiapine, followed by the management of symptoms. | Currently, no definitive antidote exists to reverse quetiapine toxicity; however, in a case report, the patient developed toxicity secondary to quetiapine, characterized by hypotension, tachycardia, altered sensorium, and electrocardiogram (ECG) showed a QT interval of 110 milliseconds. After the initial failure of symptomatic management, the patient was treated successfully after administration of Intravenous lipid emulsions (ILEs) (a source of calories and essential fatty acids rendered for patients who do not tolerate enteral nutrition) at a dose of 1.5 mg/kg for up to two doses 15 minutes apart. Rapid improvement was seen in the patient after 30 minutes. It is proposed that it might be because of the lipophilic nature of quetiapine. Similarly, the beneficial effect of ILE was also reported by Bartos and Knudsen in resuscitating patients with cardiovascular collapse. Another case series study reported successful reversal of significantly altered mental status with physostigmine (a muscarinic agonist). | The mechanism of action of quetiapine, as with other drugs used to treat schizophrenia, is unknown. However, it is thought that the drug's therapeutic activity in schizophrenia is mediated through a combination of dopamine type 2 (D2) and serotonin type 2 (5HT<sub>2</sub>) receptor antagonism. Although quetiapine is known to bind other receptors with similar affinity, only the dopamine D2 and serotonin 5HT<sub>2</sub> receptor binding is responsible for quetiapine's therapeutic activity in schizophrenia.
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REACH注册ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

2-(2-(4-(二苯并[b,F][1,4]硫氮杂卓-11-基)哌嗪-1-基)乙氧基)乙基乙酸酯置于sodium Hydroxide,水体系中,用甲醇用作溶剂,化学反应生成喹硫平
参考文献:Process For The Preparation Of A Thiazepine Derivative
标题:Process For The Preparation Of A Thiazepine Derivative
摘要:本发明涉及一种制备生物活性噻吩环衍生物的过程.本发明更具体地涉及一种改进的制备式(i)的二苯并[b,F][1,4]噻吩环衍生物的过程.

海关参考信息

2902300000-甲苯
2905310000-1,2-乙二醇
2909110000-乙醚
2921211000-乙二胺
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-2012177593-A1
优先权日:2009-07-20
标题 :Synthesis of dendrimer conjugates
发明人：BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH
权利人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH; UNIV MICHIGAN
摘要:The present invention relates to novel methods of synthesis of therapeutic and diagnostic dendrimers. In particular, the present invention is directed to novel dendrimer conjugates, novel methods of synthesizing the same, compositions comprising the conjugates, as well as systems and methods utilizing the conjugates (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease (e.g., cancer, inflammatory disease) diagnosis and/or therapy, pain therapy, etc.)). Accordingly, dendrimer conjugates of the present invention may further comprise at least two different components for targeting, imaging, sensing, and/or providing a therapeutic or diagnostic material and/or monitoring response to therapy. Furthermore, the novel synthesis methods of certain embodiments of the present invention provide significant advantages with regard to total reaction time and simplicity.

专利号:US-8389716-B2
优先权日:2009-01-30
标题:Process for the synthesis of quetiapine
发明人：SERAFINI SIRO; TOMASI FILIPPO; GALVAGNI MARCO
权利人:SERAFINI SIRO; TOMASI FILIPPO; GALVAGNI MARCO; ITALIANA SINT SPA
摘要:The present invention relates to a process for the synthesis of quetiapine. In particular, a process is provided for the synthesis of quetiapine of formula (A) comprising reacting dibenzo[b,f][1,4]thiazepin-11(10H)-one, intermediate (I) with phosphorous oxychloride to give 11-chlorodibenzo[b,f][1,4]thiazepine, intermediate (II) wherein the said reaction of intermediate (I) to intermediate (II) is performed in an organic solvent in the presence of a mixture of an organic base together with an inorganic base.

专利号:US-10005720-B2
优先权日:2013-04-05
标题:Compounds useful for the treatment of metabolic disorders and synthesis of the same
发明人：SEXTON JONATHAN Z; BRENMAN JAY E; MUSSO DAVID L
权利人:NORTH CAROLINA CENTRAL UNIV; UNIV NORTH CAROLINA CHAPEL HILL
摘要:The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

专利号:US-9315483-B2
优先权日:2007-09-13
标题 :Synthesis of deuterated catechols and benzo[D][1,3]dioxoles and derivatives thereof
发明人：JONES ANDREW D; ZELLE ROBERT E; SILVERMAN I ROBERT
权利人:CONCERT PHARMACEUTICALS INC
摘要:The present invention provides a convenient and efficient process for the synthesis of d 2 -benzo[d][1,3]dioxoles.

专利号:US-7071331-B2
优先权日:2003-02-22
标题 :Synthesis of quetiapine and pharmaceutically acceptable salts thereof
发明人：DILLER DOV; DOLITZKY BEN-ZION
权利人:TEVA PHARMA
摘要:Provided is a novel synthesis of quetiapine employing phase transfer catalyst.

专利号:EP-1660469-B1
优先权日:2003-07-18
标题 :Process for the preparation of 11-(1-piperazinyl)dibenzo 'b, f! '1 ,4!-thiazepine, an intermediate in the synthesis of the antipsychotic drug quetiapine
发明人：KACZMAREK LUKASZ; BADOWSKA-ROSLONEK KATARZYNA; STOLARCZYK ELZBIETA; SZELEJEWSKI WIESLAW
权利人:HELM AG; INST FARMACEUTYCZNY
摘要:A process for the preparation of 11-(1-piperazinyl)dibenzo-[b, f ] [ 1, 4 ] thiazepine comprising reacting phenyl 2Â(phenylthio) phenylcarbamate with piperazine and cyclizing the obtained N-[ (2 -phenylthio) phenyl ] -1 -piperazinylcarboxamide in a presence of cyclizing agent. 11-(1-piperazinyl)-dibenzo [b, f] [1, 4]thiazepine is itself, an intermediate in the synthesis of antipsychotic drug Quetiapine.

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主要参考文献

1: He Q, Zhu P, Liu X, Huo C. Association of new-onset diabetes mellitus in adults with schizophrenia treated with clozapine versus patients treated with olanzapine, risperidone, or quetiapine: A systematic review and meta-analysis. Schizophr Res. 2024 Aug 6;271:371-379. doi: 10.1016/j.schres.2024.07.028. Epub ahead of print.
85:148-154. doi: 10.1016/j.genhosppsych.2023.10.016. Epub 2023 Oct 24.
3: Kikuchi Y, Kurosawa M, Sakata M, Takahashi Y, Yamamoto K, Tomita H, Yoshio T, Yasui-Furukori N. Effects of titration speed, gender, obesity and concomitant medications on the risk and onset time of clozapine-associated fever among Japanese patients with schizophrenia: retrospective review of charts from 21 hospitals. Br J Psychiatry. 2024 Aug

合成参考文献

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参考文献:10.2165/11533060-000000000-00000
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参考文献:10.2165/11530130-000000000-00000
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参考文献:10.1186/1752-1947-4-6
摘要:Baune BT, Eyre H. Anti-inflammatory effects of antidepressant and atypical antipsychotic medication for the treatment of major depression and comorbid arthritis: a case report. Journal of Medical Case Reports. 2010 Jan 12;4(1):6. doi: 10.1186/1752-1947-4-6.
参考文献:10.1007/s00228-005-0028-4
摘要:Zesiewicz TA, Pathak A, Sullivan KL, Shamayev M, Hauser RA. Treatment of chorea with levetiracetam. European Journal of Clinical Pharmacology. 2005 Dec 01;62(1):87. doi: 10.1007/s00228-005-0028-4.

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