4-亚硝基磺胺甲恶唑 | 131549-85-4

• 物质功能分类: 分析化学 - 分析试剂 - 离子色谱试剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-亚硝基磺胺甲恶唑
• 英文名称: nitroso sulfamethoxazole
• 英文别名: 4-Nitrososulfamethoxazole；N-(5-methyl-1,2-oxazol-3-yl)-4-nitrosobenzenesulfonamide
• CAS: 131549-85-4
• 化学式: C₁₀H₉N₃O₄S
• 分子量: 267.265
• InChiKey: GHNQGDUYHCZZPT-UHFFFAOYSA-N

物化性质

• 熔点：
  >180°C (dec.)
• 沸点：
  472.9±55.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、乙酸乙酯（微溶、加热）、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

ADMET

代谢

4-硝基磺胺甲恶唑是人类已知的代谢物，包括[(2R)-2-[[(4S)-4-氨基-4-羧基丁酰基]氨基]-3-(羧甲基氨基)-3-氧代丙基]硫基-[4-[(5-甲基-1,2-恶唑-3-基)磺酰氨基]苯基]-氧代铵。

4-Nitrososulfamethoxazole has known human metabolites that include [(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]-oxoazanium.

来源:NORMAN Suspect List Exchange

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37
• 危险类别码：
  R36/37/38,R43
• WGK Germany：
  3
• 储存条件：
  -20°C 冰箱，在惰性气氛下保存

反应信息

• 作为反应物：
  描述：

  谷胱甘肽杂质 、 4-亚硝基磺胺甲恶唑 以 二甲基亚砜 为溶剂， 反应 20.0h， 生成 磺胺甲恶唑 、 glutathione disulfide 、 (S)-2-Amino-4-[(S)-1-(carboxymethyl-carbamoyl)-2-sulfino-ethylcarbamoyl]-butyric acid 、 、 、
  参考文献：
  名称：

  Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: Implications for immune mediated toxicity

  摘要：

  Sulphamethoxazole hydroxylamine (SMX-NHOH) and nitroso sulphamethoxazole (SMX-NO) were prepared by a modified literature procedure. SMX-NO produced a complex set of unstable intermediates with sulphur nucleophiles, but did not react with amino containing compounds. No reactions were observed between sulphamethoxazole (SMX)/SMX-NHOH and the nucleophiles used in this study. Thus antigens formed from N-oxidation of SMX are likely to be unstable in vivo. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00260-0
• 作为产物：
  描述：

  磺胺甲恶唑羟胺 在 iron(III) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 以40%的产率得到4-亚硝基磺胺甲恶唑
  参考文献：
  名称：

  对芳胺苯甲磺酰胺的交叉反应性免疫反应的代谢和化学起源：对羟胺和亚硝基衍生物的T细胞反应。

  摘要：

  暴露于磺胺甲恶唑（SMX）与人类患者的T细胞介导的超敏反应有关。假定的代谢物亚硝基SMX可以刺激T细胞，该代谢物与蛋白质不可逆地结合。合成了三种芳胺苯磺酰胺，磺胺噻唑，磺胺嘧啶和磺胺吡啶的羟胺和亚硝基衍生物，并探讨了它们在小鼠中的T细胞刺激能力。亚硝基衍生物是通过三步法合成的，包括形成硝基和羟胺磺酰胺中间体。为了免疫激活，雌性Balb-c品系小鼠每周四次给药亚硝基磺酰胺，持续2周。14天后，将分离的脾细胞与母体化合物羟胺代谢物一起温育，和亚硝基衍生物来测量抗原特异性增殖。为了探索不可逆蛋白结合对脾细胞活化的需求，在存在或不存在谷胱甘肽的情况下，将脾细胞与亚硝基衍生物一起孵育。亚硝基磺酰胺致敏小鼠的脾细胞在用亚硝基衍生物而不是母体化合物刺激后增殖并分泌白介素（IL）-2，IL-4，IL-5和粒细胞单核细胞集落刺激因子。还用结构相关的磺酰胺的羟胺和亚硝基衍生物刺激了致敏小鼠的脾细胞增殖。谷胱甘

  DOI：

  10.1021/tx900329b

文献信息

• Improved alkaline water electrolysis system for green energy: sulfonamide antibiotic-assisted anodic oxidation integrated with hydrogen generation
  作者：Qiwei Zhang、Yuhang Tong、Zhuowen Wang、Baojian Jing、Yingshi Zhu、Shan Qiu、Chongwei Cui、Fengxia Deng

  DOI：10.1039/d2ta08850a

  日期：——

  wastewater with hydrogen generation, an electrochemical system was built to combine the anodic sulfamethoxazole (SMX) degradation reaction with the cathodic hydrogen evolution reaction (HER). This system showed an excellent pollutant removal efficiency (92.99% ± 3.5%) and H2 yield with only a cell voltage of 2.37 V at 100 mA cm−2. This is attributed to a synergistic effect of indirect oxidation through Fe(VI)

  为了将抗生素污染废水的处理与制氢相结合，建立了一个电化学系统，将阳极磺胺甲恶唑 (SMX) 降解反应与阴极析氢反应 (HER) 相结合。该系统在 100 mA cm -2的电池电压仅为 2.37 V 时显示出出色的污染物去除效率 (92.99% ± 3.5%) 和 H 2产率。这归因于通过 Fe( VI ) 间接氧化和直接氧化的协同效应，分别占总去除量的约 30% 和 60%。为了进一步揭示 Fe( VI），基于密度泛函理论（DFT）分析了静电势。基于通过LC-MS 和量子化学计算检测到的中间体，提出了可能的 SMX 降解途径。我们利用 SMX 氧化反应代替析氧反应 (OER)。这项工作为设计与废水处理和可再生能源生产相结合的潜在系统提供了思路。
• Insights into the electrochemical degradation of sulfamethoxazole and its metabolite by Ti/SnO2-Sb/Er-PbO2 anode
  作者：Yanping Wang、Chengzhi Zhou、Jinhua Wu、Junfeng Niu

  DOI：10.1016/j.cclet.2020.03.073

  日期：2020.10

  Electrochemical degradation of sulfamethoxazole (SMX) and its metabolite acetyl-sulfamethoxazole (Ac-SMX) by Ti/SnO2-Sb/Er-PbO2 were investigated. Results indicated that the electrochemical degradation of SMX and Ac-SMX followed pseudo-first-order kinetics. The rate constants of SMX and Ac-SMX were 0.268 and 0.072 min(-1) at optimal current density of 10 and 14 mA/cm(2), respectively. Transformation products of SMX and Ac-SMX were identified and the possible degradation pathways, including the cleavage of S-N bond, opening ring of isoxazole and nitration of amino group, were proposed. Total organic carbon removal of SMX was nearly 63.2% after 3 h electrochemical degradation. 22.4% nitrogen of SMX was transformed to NO3-, and 98.8% sulfur of SMX was released as SO42-. According to quantitative structure-activity relationship model, toxicities of SMX and Ac-SMX to aquatic organisms significantly decreased after electrochemical degradation. Electric energy consumption for 90% SMX and Ac-SMX degradation was determined to be 0.58-8.97 and 6.88-44.19 Wh/L at different experimental conditions, respectively. Compared with parent compound SMX, the metabolite Ac-SMX is more refractory and toxic, which emphasizes the importance of taking its metabolites into account when investigating the disposal of pharmaceuticals from wastewater. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Metabolic and Chemical Origins of Cross-Reactive Immunological Reactions to Arylamine Benzenesulfonamides: T-Cell Responses to Hydroxylamine and Nitroso Derivatives
  作者：J. Luis Castrejon、Sidonie N. Lavergne、Ayman El-Sheikh、John Farrell、James L. Maggs、Sunil Sabbani、Paul M. O’Neill、B. Kevin Park、Dean J. Naisbitt

  DOI：10.1021/tx900329b

  日期：2010.1.18

  intermediates. For immune activation, female Balb-c strain mice were administered nitroso sulfonamides four times weekly for 2 weeks. After 14 days, isolated splenocytes were incubated with the parent compounds, hydroxylamine metabolites, and nitroso derivatives to measure antigen-specific proliferation. To explore the requirement of irreversible protein binding for spleen cell activation, splenocytes were

  暴露于磺胺甲恶唑（SMX）与人类患者的T细胞介导的超敏反应有关。假定的代谢物亚硝基SMX可以刺激T细胞，该代谢物与蛋白质不可逆地结合。合成了三种芳胺苯磺酰胺，磺胺噻唑，磺胺嘧啶和磺胺吡啶的羟胺和亚硝基衍生物，并探讨了它们在小鼠中的T细胞刺激能力。亚硝基衍生物是通过三步法合成的，包括形成硝基和羟胺磺酰胺中间体。为了免疫激活，雌性Balb-c品系小鼠每周四次给药亚硝基磺酰胺，持续2周。14天后，将分离的脾细胞与母体化合物羟胺代谢物一起温育，和亚硝基衍生物来测量抗原特异性增殖。为了探索不可逆蛋白结合对脾细胞活化的需求，在存在或不存在谷胱甘肽的情况下，将脾细胞与亚硝基衍生物一起孵育。亚硝基磺酰胺致敏小鼠的脾细胞在用亚硝基衍生物而不是母体化合物刺激后增殖并分泌白介素（IL）-2，IL-4，IL-5和粒细胞单核细胞集落刺激因子。还用结构相关的磺酰胺的羟胺和亚硝基衍生物刺激了致敏小鼠的脾细胞增殖。谷胱甘
• Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: Implications for immune mediated toxicity
  作者：Dean J. Naisbitt、Paul M. O'Neill、Munir Pirmohamed、B. Kevin Park

  DOI：10.1016/s0960-894x(96)00260-0

  日期：1996.7

  Sulphamethoxazole hydroxylamine (SMX-NHOH) and nitroso sulphamethoxazole (SMX-NO) were prepared by a modified literature procedure. SMX-NO produced a complex set of unstable intermediates with sulphur nucleophiles, but did not react with amino containing compounds. No reactions were observed between sulphamethoxazole (SMX)/SMX-NHOH and the nucleophiles used in this study. Thus antigens formed from N-oxidation of SMX are likely to be unstable in vivo. Copyright (C) 1996 Elsevier Science Ltd