喹硫平亚砜 | 329216-63-9

• 物质功能分类: 化学试剂 - 有机试剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 中文名称: 喹硫平亚砜
• 中文别名: 喹硫平磺酸盐
• 英文名称: Quetiapine sulfoxide
• 英文别名: 2-[2-[4-(5-oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]ethanol；quetiapine S-oxide；2-[2-[4-(11-oxobenzo[b][1,4]benzothiazepin-6-yl)piperazin-1-yl]ethoxy]ethanol
• CAS: 329216-63-9
• 化学式: C₂₁H₂₅N₃O₃S
• 分子量: 399.514
• InChiKey: FXJNLPUSSHEDON-UHFFFAOYSA-N

物化性质

• 熔点：
  ~48°C
• 沸点：
  611.3±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.37
• 氢给体数：
  1.0
• 氢受体数：
  6.0

安全信息

• 储存条件：
  2-8℃

制备方法与用途

Quetiapine sulfoxide 是 Quetiapine 的代谢产物。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  喹硫平	Quetiapine	111974-69-7	C21H25N3O2S	383.514
  喹硫平 N-氧化物	quetiapine N19-oxide	1076199-40-0	C21H25N3O3S	399.514

反应信息

• 作为产物：
  描述：

  11-(4-[2-(2-hydroxyethoxy)ethyl]-1-piperazinyl)dibenzo[b,f]-1,4-thiazepine hydrochloride 在 sodium periodate 作用下， 反应 22.0h， 以1.98 g的产率得到喹硫平亚砜
  参考文献：
  名称：

  Behavioral Approach to Nondyskinetic Dopamine Antagonists:  Identification of Seroquel

  摘要：

  A great need exists for antipsychotic drugs which will not induce extrapyramidal symptoms (EPS) and tardive dyskinesias (TDs). These side effects are deemed to be a consequence of nonselective blockade of nigrostriatal and mesolimbic dopamine D2 receptors. Nondyskinetic clozapine (1) is a low-potency D2 dopamine receptor antagonist which appears to act selectively in the mesolimbic area. In this work dopamine antagonism was assessed in two mouse behavioral assays: antagonism of apomorphine-induced climbing and antagonism of apomorphine-induced disruption of swimming. The potential for the liability of dyskinesias was determined in haloperidol-sensitized Cebus monkeys. Initial examination of a few close cogeners of 1 enhanced confidence in the Cebus model as a predictor of dyskinetic potential. Considering dibenzazepines, 2 was not dyskinetic whereas 2a was dyskinetic. Among dibenzodiazepines, 1 did not induce dyskinesias where as its N-2-(2-hydroxyethoxy)ethyl analogue 3 was dyskinetic. The emergence of such distinctions presented an opportunity. Thus, aromatic and N-substituted analogues of 6-(piperazin-1-yl)-11H-dibenz[b,e]azepines and 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepines and -oxazepines were prepared and evaluated. 11-(4-[2-(2-Hydroxyethoxy)ethyl]piperazin-1-yl)dibenzo[b,f][1,4]thiazepine (23) was found to be an apomorphine antagonist comparable to clozapine. It was essentially nondyskinetic in the Cebus model. With 23 as a platform, a number of N-substituted analogues were found to be good apomorphine antagonists but all were dyskinetic.

  DOI：

  10.1021/jm000242+

文献信息

• Synthesis and Oxidant Properties of Phase 1 Benzepine N-Oxides of Common Antipsychotic Drugs
  作者：Udo Nubbemeyer、Jochen Körber、Stefan Löffler、Dieter Schollmeyer

  DOI：10.1055/s-0033-1338519

  日期：——

  In the osmium tetroxide catalyzed dihydroxylation of styrene or cinnamyl alcohol and in the tetrapropylammonium perruthenate catalyzed oxidation of cinnamyl alcohol, the benzepine N-oxides could be used as replacements for the standard oxidant, N-methylmorpholine N-oxide (NMO) with varying degrees of efficiency. From a chemical point of view, clozapine N-oxide displayed a comparable oxidation power

  摘要 越来越多的证据表明，广泛使用的抗精神病药会氧化细胞成分，但直到现在，基本化学仍不清楚。众所周知，这类药物容易经历N-氧化作为第一步关键的代谢步骤。为了深入了解问题，第三阶段1个ñ -oxides氯氮平，奥氮平，喹硫平，和佐替平，合成，与一起Ñ，小号-dioxides喹硫平与佐替平的。这些N然后对氧化物进行完善的化学转化，以测试其在第VIII族过渡金属催化的反应中的氧化性能。在四氧化催化的苯乙烯或肉桂醇的二羟基化反应中以及在四丙基过钌酸催化的肉桂醇的氧化反应中，苯并pine庚因N-氧化物可以替代标准氧化剂N-甲基吗啉N-氧化物（NMO）效率。从化学角度看，氯氮平N氧化物显示出可与NMO媲美的氧化能力，表明苯并ze以氧为载体。此外，发现喹硫平是优良的双氧受体，经历了最初的N-氧化和随后的S-氧化。因此，值得考虑的是，对人体的氧化损伤是否可能与普通抗精神病药的潜在氧化还原特性有关。 越来越
• A study of photodegradation of quetiapine by the use of LC-MS/MS method
  作者：Robert Skibiński

  DOI：10.2478/s11532-011-0133-4

  日期：2012.2.1

  Photodegradation of quetiapine under UVC irradiation in methanol solution was investigated and structural elucidation of its photodegradation products was performed with the use of the reversed phase UHPLC system coupled with accurate mass hybrid ESI-Q-TOF mass spectrometer. During one run all essential data for the determination of photodegradation kinetics and for the structural elucidation of the products was collected with the use of auto MS/MS mode. Five degradation products were found and their masses and formulas were obtained with high accuracy (0.26–5.02 ppm). For all the analyzed compounds, MS/MS fragmentation spectra were also obtained allowing structural elucidation of the unknown degradation products and indicating photodegradation pathways of quetiapine. The main photodegradation product was identified as 2-[2-[4-(5-oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]-ethanol and the photodegradation reaction yields the first-order kinetics with the rate constant k = 0.1094 h−1.

  摘要：本研究调查了在甲醇溶液中UVC辐射下喹硫平的光降解，并使用反相UHPLC系统结合精确质量杂化ESI-Q-TOF质谱仪对其光降解产物进行结构阐明。在一次运行中，使用自动MS/MS模式收集了用于确定光降解动力学和产物结构阐明的所有必要数据。发现了五种降解产物，并且它们的质量和公式得到了高精度的确定（0.26-5.02 ppm）。对于所有分析化合物，还获得了MS/MS碎片谱，以便结构阐明未知的降解产物，并指示喹硫平的光降解途径。主要的光降解产物被确定为2-[2-[4-(5-氧化二苯并[b,f][1,4]噻唑啉-11-基)-1-哌嗪基]乙氧基]-乙醇，光降解反应产生的速率常数k为0.1094 h^-1，符合一级动力学。
• METHODS OF MONITORING ADHERENCE TO QUETIAPINE THERAPY
  申请人：Ameritox, Ltd.

  公开号：US20160041192A1

  公开（公告）日：2016-02-11

  The present disclosure provides methods for monitoring subject (e.g., patient) adherence to quetiapine therapy, for example as a component of treating a subject for a mental health disorder such as schizophrenia, bipolar disorder or major depressive disorder.