S-(N,N-diethylcarbamoyl)glutathione | 157723-51-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(N,N-diethylcarbamoyl)glutathione
• 英文别名: L-gamma-Glutamyl-S-(diethylcarbamoyl)-L-cysteinylglycine；(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-(diethylcarbamoylsulfanyl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 157723-51-8
• 化学式: C₁₅H₂₆N₄O₇S
• 分子量: 406.46
• InChiKey: WZXBYDBYBIGAQN-UWVGGRQHSA-N

物化性质

• 熔点：
  228-230°C
• 溶解度：
  可溶于酸性水溶液（轻微）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  204
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  S-(N,N-diethylcarbamoyl)glutathione 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 S-(N,N-diethylcarbamoyl)glutathione hydrochloride
  参考文献：
  名称：

  [EN] SALT FORMS OF S-(N, N-DIETHYLCARBAMOYL)GLUTATHIONE
  [FR] FORMES SALINES DE S-(N, N-DIÉTHYLCARBAMOYL)GLUTATHION

  摘要：

  该发明涉及盐形式S-(N,N-二乙基氨甲酰)谷胱甘肽的各种方面，一种制备该盐形式的方法，包括所述盐形式的药物组合物。该发明还涉及一种预防或治疗谷氨酸相关疾病的方法，包括向所述受试者投予所述盐形式的治疗有效量。

  公开号：

  WO2020194058A1
• 作为产物：
  描述：

  谷胱甘肽 、 N,N-二乙基氯甲酰胺 在 吡啶 作用下， 以 水 为溶剂， 反应 0.5h， 以29%的产率得到S-(N,N-diethylcarbamoyl)glutathione
  参考文献：
  名称：

  [EN] SALT FORMS OF S-(N, N-DIETHYLCARBAMOYL)GLUTATHIONE
  [FR] FORMES SALINES DE S-(N, N-DIÉTHYLCARBAMOYL)GLUTATHION

  摘要：

  该发明涉及盐形式S-(N,N-二乙基氨甲酰)谷胱甘肽的各种方面，一种制备该盐形式的方法，包括所述盐形式的药物组合物。该发明还涉及一种预防或治疗谷氨酸相关疾病的方法，包括向所述受试者投予所述盐形式的治疗有效量。

  公开号：

  WO2020194058A1

文献信息

• Method for treatment of glutamate related disorders
  申请人：——

  公开号：US20010031730A1

  公开（公告）日：2001-10-18

  Disclosed are novel compounds and novel pharmaceutical compositions for use in medical therapy, as well as intermediates and processes for preparing such compounds. Therapeutic methods for preventing or treating glutamate-related disorders in a mammal and methods to inhibit or prevent glutamate binding in mammalian tissue are also disclosed.

  本发明涉及新型化合物和新型药物组合物，用于医疗治疗，以及制备这些化合物的中间体和过程。还公开了在哺乳动物中预防或治疗谷氨酸相关疾病的治疗方法，以及抑制或预防哺乳动物组织中谷氨酸结合的方法。
• Therapeutic compositions
  申请人：Schloss V. John

  公开号：US20050130904A1

  公开（公告）日：2005-06-16

  A method is provided for the preparation of compounds of the formula (R 1 )(R 2 )NC(═X)S(O) n R 3 or (R 1 )(R 2 )NC(═X)OS(O) n R 3 , wherein R 1 , R 2 and R 3 , X and n have any of the meanings defined in the specification. A method is also provided for the detection and quantitation of compounds of the formula (R 1 )(R 2 )NC(═X)OS(O) n R 3 . A method to link a therapeutic agent to a compound that is conjugated to glutathione is also provided for the purpose of improving the therapeutic properties of the therapeutic agent. Novel compounds, intermediates, pharmaceutical compositions and methods of use are also provided.

  提供了一种制备式（R 1 )(R 2 )NC(═X)S(O) n R 3 或（R 1 )(R 2 )NC(═X)OS(O) n R 3 其中 R 1 , R 2 和 R 3 X 和 n 具有说明书中定义的任何含义。还提供了一种检测和定量式（R 1 )(R 2 NC(═X)OS(O) n R 3 .为了改善治疗剂的治疗特性，还提供了一种将治疗剂与谷胱甘肽共轭的化合物连接的方法。还提供了新型化合物、中间体、药物组合物和使用方法。
• Glutathione Carbamoylation with S-Methyl N,N-diethylthiolcarbamate Sulfoxide and Sulfone
  作者：Nagendra S Ningaraj、John V Schloss、Todd D Williams、Morris D Faiman

  DOI：10.1016/s0006-2952(97)00513-3

  日期：1998.3

  S-Methyl N,N-diethylthiolcarbamate sulfoxide (DETC-MeSO) and sulfone (DETC-MeSO2) both inhibit rat liver low K-m aldehyde dehydrogenase (ALDH(2)) in vitro and in vivo (Nagendra et al., Biochem Pharmacol 47: 1465-1467, 1994). DETC-MeSO has been shown to be a metabolite of disulfiram, but DETC-MeSO2 has not. Studies were carried out to further investigate the inhibition of ALDH(2) by DETC-MeSO and DETC-MeSO2. In an in vitro system containing hydrogen peroxide and horseradish peroxidase, the rate of DETC-MeSO oxidation corresponded to the rate of DETC-MeSO2 formation. Carbamoylation of GSH by both DETC-MeSO and DETC-MeSO2 was observed in a rat liver S-9 fraction. Carbamoylation of GSH was not observed in the presence of N-methylmaleimide. In in vitro studies, DETC-MeSO and DETC-MeSO2 were equipotent ALDH(2) inhibitors when solubilized mitochondria were used, but DETC-MeSO was approximately four times more potent than DETC-MeSO2 in intact mitochondria. In studies with rats, the dose (i.p. or oral) required to inhibit 50% ALDH(2) (ED50) was 3.5 mg/kg for DETC-MeSO and approximately 35 mg/kg for DETC-MeSO2, approximately a 10-fold difference. Furthermore, maximum ALDH(2) inhibition occurred 1 hr after DETC-MeSO administration, whereas maximal ALDH(2) inhibition occurred 8 hr after DETC-MeSO2 dosing. DETC-MeSO is, therefore, not only a more potent ALDH(2) inhibitor than DETC-MeSO2 in vivo, but also in vitro when intact mitochondria are utilized. The in vitro results thus support the in vivo findings. Since oxidation of DETC-MeSO can occur both enzymatically and non-enzymatically, it is possible that DETC-MeSO2 is formed in vivo. DETC-MeSO2, however, is not as effective as DETC-MeSO in inhibiting ALDH(2), probably because it has difficulty penetrating the mitochondrial membrane. Thus, even if DETC-MeSO2 is formed in vivo from DETC-MeSO, it is the metabolite DETC-MeSO that is most likely responsible for the inhibition of ALDH(2) after disulfiram administration. (C) 1998 Elsevier Science Inc.
• SALT FORMS OF S-(N, N-DIETHYLCARBAMOYL)GLUTATHIONE
  申请人：Tonix Pharma Holdings Limited

  公开号：EP3946601A1

  公开（公告）日：2022-02-09
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF NEURONAL INJURY
  申请人：AXCELLA HEALTH INC.

  公开号：US20190046486A1

  公开（公告）日：2019-02-14

  This disclosure provides compositions and methods for treating or preventing neuronal injury in a subject, e.g., a subject at risk of or having traumatic brain injury or stroke.