Pregnenolon-3β-sulfonsaeureester | 1247-64-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Pregnenolon-3β-sulfonsaeureester
• 英文别名: [(3S,10R,13S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
• CAS: 1247-64-9；51922-44-2；87761-10-2
• 化学式: C₂₁H₃₂O₅S
• 分子量: 396.548
• InChiKey: DIJBBUIOWGGQOP-WPVPORHCSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：62.5 mg/mL（157.61 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

制备方法与用途

生物活性

Pregnenolone monosulfate（3β-羟基-5-孕烯-20-酮单硫酸盐）是一种功能强大的神经甾体，是包括甾体酮在内的多种甾体激素的主要前体。它还是大麻素 CB1 受体信号传导的特异性抑制剂，能够抑制由 CB1 受体介导的大麻素（如四氢大麻酚 THC）的作用，并保护大脑免受大麻中毒的影响。

靶点

| CB1 | 人类内源性代谢物 |

体外研究

激活 CB1 受体会增加脑部孕烯醇酮水平，进而对 CB1 受体的活性产生负反馈作用，拮抗大多数已知的行为和生理效应。Pregnenolone 很可能作为特异性的非竞争性负共价调节剂，与正构配体占据不同的位点。Pregnenolone 并不改变激动剂结合，仅影响其效能。

在 THC 诱导的配对脉冲比（PPR）增加中，预先用 Pregnenolone (100 nM) 处理显著抑制了这一效应（15.1±1.8 % 的抑制）。这些效果可能归因于 Pregnenolone 在突触前的作用机制。

体内研究

Pregnenolone（2-6 mg/kg）给药能够阻断大麻素诱导的食物摄入，并减轻 THC 引起的记忆损害。然而，它本身并不会改变这些行为。预先注射 Pregnenolone (2 和 4 mg/kg) 可以减少 WIN 55,212-2 的摄入量，并降低渐进比例递增程序中的断点。

文献信息

• Antagonists of CB1 receptor
  申请人：INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE)

  公开号：US10040816B2

  公开（公告）日：2018-08-07

  The invention relates to an antagonist of CB1 receptor for use in the treatment of a pathologic condition or disorder selected from the group consisting of bladder and gastrointestinal disorders; inflammatory diseases; cardiovascular diseases; nephropathies; glaucoma; spasticity; cancer; osteoporosis; metabolic disorders; obesity; addiction, dependence, abuse and relapse related disorders; psychiatric and neurological disorders; neurodegenerative disorders; autoimmune hepatitis and encephalitis; pain; reproductive disorders and skin inflammatory and fibrotic diseases.

  本发明涉及一种 CB1 受体拮抗剂，用于治疗选自以下组别的病理状况或紊乱：膀胱和胃肠道疾病；炎症性疾病；心血管疾病；肾病；青光眼；痉挛；癌症；骨质疏松症；代谢紊乱；肥胖；成瘾、依赖、滥用和复发相关紊乱；精神和神经紊乱；神经退行性疾病；自身免疫性肝炎；骨质疏松症；代谢紊乱；肥胖；成瘾、依赖、滥用和复发相关疾病；精神和神经系统疾病；神经退行性疾病；自身免疫性肝炎和脑炎；疼痛；生殖系统疾病以及皮肤炎症和纤维化疾病。
• Antagonists of CB1 Receptor
  申请人：INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE)

  公开号：US20160145294A1

  公开（公告）日：2016-05-26

  The invention relates to an antagonist of CB1 receptor for use in the treatment of a pathologic condition or disorder selected from the group consisting of bladder and gastrointestinal disorders; inflammatory diseases; cardiovascular diseases; nephropathies; glaucoma; spasticity; cancer; osteoporosis; metabolic disorders; obesity; addiction, dependence, abuse and relapse related disorders; psychiatric and neurological disorders; neurodegenerative disorders; autoimmune hepatitis and encephalitis; pain; reproductive disorders and skin inflammatory and fibrotic diseases.
• COMPOSITIONS AND METHODS COMPRISING YEAST ORGANISMS AND LIPID EXTRACTS THEREOF
  申请人：R.F. Technology Consultants, Inc.

  公开号：US20160375071A1

  公开（公告）日：2016-12-29

  The invention provides compositions comprising whole yeast organisms and/or lipid yeast extract. Such compositions may be medical or cosmetic compositions, comprising one or more cosmetic or medical, pharmaceutical ingredients. The invention comprises methods of making such compositions. The yeast components of the compositions may be derived from yeast cultures which comprise at least 0.1% oil by dry weight.
• ANTAGONISTS OF CB1 RECEPTOR
  申请人：INSERM (Institut National de la Sante et de la Recherche Medicale)

  公开号：US20220153776A1

  公开（公告）日：2022-05-19

  The invention relates to an antagonist of CB1 receptor for use in the treatment of a pathologic condition or disorder selected from the group consisting of bladder and gastrointestinal disorders; inflammatory diseases; cardiovascular diseases; nephropathies; glaucoma; spasticity; cancer; osteoporosis; metabolic disorders; obesity; addiction, dependence, abuse and relapse related disorders; psychiatric and neurological disorders; neurodegenerative disorders; autoimmune hepatitis and encephalitis; pain; reproductive disorders and skin inflammatory and fibrotic diseases.