(3β)-3-(sulfooxy)pregn-5-en-20-one sodium salt | 1852-38-6

• 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: (3β)-3-(sulfooxy)pregn-5-en-20-one sodium salt
• 英文别名: pregnenolone sulfate sodium；pregnenolone sulfate；pregnenolone sulfate sodium salt；pregnenolone-SO4；sodium;[(3S,8S,9S,10R,13S,14S,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] sulfate
• CAS: 1852-38-6
• 化学式: C₂₁H₃₁O₅S*Na
• 分子量: 418.53
• InChiKey: QQVJEIZJHDPTSH-UTNKIXDHSA-M

物化性质

• 熔点：
  192 °C(lit.)
• 溶解度：
  溶于甲醇和水的混溶液中，1.93mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  28
• 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：
  91.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C，密闭保存，置于干燥处。

制备方法与用途

生物活性

Pregnenolone monosulfate sodium盐（3β-羟基-5孕烯-20-one单硫酸钠盐）是一种强大的神经甾体，是包括孕酮在内的多种甾体激素的主要前体。它也是大麻素CB1受体信号传导的特异性抑制剂，能够抑制由CB1受体介导的大麻酚（THC）的作用，并保护大脑免受大麻毒素的影响。

靶点

• CB1
• 人体内源性代谢物

体外研究

CB1受体刺激会增加脑内的Pregnenolone水平，从而对CB1受体的活动产生负反馈作用，对抗THC大多数已知的行为和生理效应。Pregnenolone很可能作为信号特异性负配体调节剂，结合在不同于正配体占据位点的不同位置。它不改变激动剂结合，仅影响激动剂效力。当预先用100 nM Pregnenolone处理切片时（抑制率为15.1±1.8%），THC的效果显著减弱。Pregnenolone主要通过预突触作用起效，能阻止THC引起的配对脉冲比值增加，而不改变迷你EPSC的幅度或衰减时间。

体内研究

Pregnenolone（2-6 mg/kg）在Wistar大鼠和C57BL/6N小鼠中阻断了THC诱导的食物摄入，并缓解了THC引起的小鼠记忆障碍。但这些行为本身并未受到影响。预先注射Pregnenolone（2和4 mg/kg）可减少WIN 55,212-2的摄入量，并降低递增比率程序中的击破点。

反应信息

• 作为反应物：
  描述：

  (3β)-3-(sulfooxy)pregn-5-en-20-one sodium salt 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 以97%的产率得到孕烯醇酮
  参考文献：
  名称：

  一种新的温和的PTSA催化的硫酸酯水解和酸催化的12-乙酰基-二烯-11-醇四环三萜类化合物的硫酸催化重排，涉及角甲基迁移

  摘要：

  含有12-乙酰基-Δ8,14-二烯-11-ol部分的四环三萜类化合物经历了一系列的酸催化重排。已经对重排产物进行了表征，已经阐明了用于重排的合理机制，并且已经开发了条件以提供高产率的重排产物。开发了一种新的，通用的PTSA·H 2 O和PPTS催化的硫酸盐水解方法。

  DOI：

  10.1016/s0040-4039(00)01190-4

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 Santé et de la Recherche Médicale)

  公开号：EP3170501B1

  公开（公告）日：2020-07-08
• METHODS FOR TREATING NEUROLOGICAL DISORDERS OR DAMAGE
  申请人：Tyers Mike

  公开号：US20090076019A1

  公开（公告）日：2009-03-19

  A clonogenic neurosphere assay is described that carries out high throughput screens (HTS) to identify potent and/or selective modulators of proliferation, differentiation and/or renewal of neural precursor cells, neural progenitor cells and/or self-renewing and multipotent neural stem cells (NSCs). Compositions comprising the identified modulators and methods of using the modulators and compositions, in particular to treat neurological disorders (e.g. brain or CNS cancer) or damage are also disclosed.
• METHODS FOR THE MODULATION OF BRAIN PROGESTAGEN SIGNALING IN THE PREVENTION AND TREATMENT OF NEUROLOGICAL DISORDERS AND NEURODEGENERATIVE DISEASES
  申请人：Atwood Craig Stephen

  公开号：US20100028360A1

  公开（公告）日：2010-02-04

  The present invention relates to methods for modulating progestagen signaling for treating neurological disorders or neurodegenerative disease, or preventing or delaying its onset in individuals deemed by competent observation and testing to be susceptible thereto. Progestagens can be administered to elevate serum and brain levels of progestagens and induce neurogenesis. Progestagen therapy may prevent some of the neurodegenerative and cognitive changes associated with developmental and aging associated neurological disorders and neurodegenerative diseases. Progestagen therapy together with suppression of GnRH, kisspeptin, LH and/or FSH signaling also may be used for treating neurological disorders or neurodegenerative diseases. The invention also relates to methods for inhibiting or delaying blastulation during embryogenesis, and neurogenesis during embryogenesis, fetal, neonatal, childhood, puberty or adult life. Blocking progestagen, estrogen and/or opioid signaling with receptor antagonists will inhibit neurogenesis. The invention also relates to using progestagens in vitro to induce neurogenesis in embryonic or adult stem cells.
• 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.