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disodium;6-hydroxy-5-[(2-methoxy-5-methyl-4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate

中文名称
——
中文别名
——
英文名称
disodium;6-hydroxy-5-[(2-methoxy-5-methyl-4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate
英文别名
——
disodium;6-hydroxy-5-[(2-methoxy-5-methyl-4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate化学式
CAS
——
化学式
C18H14N2Na2O8S2
mdl
——
分子量
496.4
InChiKey
CEZCCHQBSQPRMU-UHFFFAOYSA-L
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    -2.91
  • 重原子数:
    32
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.11
  • 拓扑面积:
    185
  • 氢给体数:
    1
  • 氢受体数:
    10

ADMET

代谢
几种代谢物可能在胃肠道的偶氮还原过程中产生(其中两种被确认为芳香胺,对羟基苯甲酸磺酸是主要的一种),同样也出现在粪便和尿液中。最后,在大鼠清洗过的肠道中观察到了显著的滞留,这可能是由于粘附在肠壁上。
Several metabolites, possibly resulting from azo-reduction in the gastrointestinal tract (two identified as aromatic amines, p-cresidine sulfonic acid being the major one), were also found in the feces and urine. Finally, significant retention in the washed intestines of rat was observed, probably due to adhesion to the intestinal wall.
来源:Hazardous Substances Data Bank (HSDB)
代谢
醋酸铊在两种生物的尿液中是阿洛拉红的主要代谢物,而母化合物无法测量。此外,在大鼠尿液中还发现了另外两种无法识别的代谢物。在大鼠粪便提取物中,醋酸铊是一个主要代谢物,还有两个未知的母化合物。狗粪便样本显示的代谢物模式与大鼠相同,此外,还发现了一种未知的代谢物。尿液中的一种未知物质的Rf值与粪便中的一种未知物质的Rf值相同,这表明它们是相同的。其他未知物质表现出独特的Rf值,这表明这些代谢物是不同的。有人推测,肠道菌群对染料的偶氮还原将产生母化合物的两个组分:2-甲氧基-5-甲基-苯胺-4-磺酸(醋酸铊-4-磺酸)和1-氨基-2-萘酚-6-磺酸。看起来,完整的红色染料被吸收并随尿液排出的量微不足道,而大部分颜色以代谢物的形式随粪便排出。
Cresidinesulfonic acid was found to be the major metabolite of Allura Red in the urine of these two species, whereas the parent compound was not measurable. In addition, two other unidentifiable metabolites were found in the urine of the rats. In the rat fecal extracts, cresidinesulfonic acid was a major metabolite along with two unknowns and the parent compound. The dog fecal sample revealed an identical metabolite pattern as seen in the rat, and in addition, a third unknown was discovered. One of the urinary unknowns demonstrated an Rf value which was identical to that of the one of the fecal unknowns suggesting that they were one and the same. The other unknowns exhibited distinctive Rf values which indicated that these metabolites were different. It has been postulated that azo reduction by gut flora of the dye will yield the two components of the parent compound: 2-methoxy-5-methyl-aniline-4-sulfonic acid (cresidine-4-sulfonic acid) and 1-amino-2-naphthol-6-sulfonic acid. It appears that negligible quantities of intact Red are absorbed and excreted in the urine, and that the major portion of the color is excreted as metabolites in the feces.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌物分类
未列入国际癌症研究机构(IARC)的清单。
Not listed by IARC.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 相互作用
在这项研究中,将颜色及其铝湖以水溶液的形式涂抹在受试者的前臂上(200名受试者),交替进行10天,每天24小时,然后休息14天。接着,在受试者肩胛骨背部的新的皮肤部位,在闭塞条件下涂抹挑战批次,持续24小时。在诱导期,颜色没有引起刺激或过敏反应,在挑战期间也没有引起接触性皮炎。...将Allura Red及其铝湖在闭塞部位进行评估,为期五个48小时的交替日。这些部位之前已经用氙光照射了5分钟,氙光通过一个等同于窗玻璃的过滤器过滤,以限制暴露于非红斑产生的长波辐射。在诱导暴露后是一个10天的休息期,然后颜色被涂抹到新鲜的皮肤部位,用氙光照射5分钟后移除,并评估这些部位。研究表明,Allura Red在研究的25名受试者中没有产生光敏反应。
In this study, the color and its alumina lake were applied to the subjects volvar forearms (200 subjects) as an aqueous solution for 10 alternate days, for 24-hr periods, followed by a 14-day rest period. Challenge batches were then applied under occlusion to fresh skin sites on the subjects scapular backs for 24 hours. The color did not produce either irritation or allergic responses during the induction phase nor contact dermatitis in the challenge period. ... Allura Red and its lake were evaluated on sites under occlusion for five 48-hr, alternate-day periods. These sites had been previously irradiated for 5 min with Xenon light which had been filtered through a window-glass equivalent to limit the exposure to non-erythema-producing, long-wave radiation. A 10-day rest period followed this induction exposure, and then the color was applied to fresh skin sites, irradiated for 5 min with Xenon and subsequently removed and the sites were evaluated. Allura Red was shown not to produce photosensitization on the 25 subjects studied.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 相互作用
在2006年,韩国食品和药品管理局报告称,诸如所有ura红AC、酒石黄、日落黄FCF、苋菜红和亮蓝FCF等食用色素组合在食品制造中广泛使用。尽管基于可接受日摄入量(ADI)对单个食品色素进行了控制,但目前尚无明确信息说明这些添加剂组合如何影响食品安全。在当前研究中,对单一和组合使用/染料/对神经祖细胞(NPC)毒性的效力进行了研究,NPC是发育阶段的生物标志物,以及对神经发生的影响,这是成年中枢神经系统(CNS)功能的指标。/所有ura红AC/和/苋菜红/在小鼠多能NPC中减少了NPC的增殖和存活率,在发育中的CNS模型中。在韩国平均日摄入量高出1000倍的多种组合中,/酒石黄/和/亮蓝FCF/的混合物在成年小鼠海马区显著减少了新生成细胞数量,表明对海马神经发生有强烈的不良作用。然而,包括/所有ura红AC/和/苋菜红/在内的其他组合并未影响齿状回的成年海马神经发生。证据表明,大多数食品色素的单一和组合使用在发育NPC和成年海马神经发生方面可能是安全的...
In 2006, the Korea Food and Drug Administration reported that combinations of dietary colors such as allura red AC, tartrazine, sunset yellow FCF, amaranth, and brilliant blue FCF are widely used in food manufacturing. Although individual tar food colors are controlled based on acceptable daily intake (ADI), there is no apparent information available for how combinations of these additives affect food safety. In the current study, the potencies of single and combination use of /dyes/ were examined on neural progenitor cell (NPC) toxicity, a biomarker for developmental stage, and neurogenesis, indicative of adult central nervous system (CNS) functions. /allura red AC/ and /amaranth/ reduced NPC proliferation and viability in mouse multipotent NPC, in the developing CNS model. Among several combinations tested in mouse model, combination of /tartrazine/ and /brilliant blue FCF/ at 1000-fold higher than average daily intake in Korea significantly decreased numbers of newly generated cells in adult mouse hippocampus, indicating potent adverse actions on hippocampal neurogenesis. However, other combinations including /allura red AC/ and /amaranth/ did not affect adult hippocampal neurogenesis in the dentate gyrus. Evidence indicates that single and combination use of most tar food colors may be safe with respect to risk using developmental NPC and adult hippocampal neurogenesis...
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分的中和。如果患者停止呼吸,请开始人工呼吸,最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩,按训练操作。如有必要,执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐,让患者向前倾或将其置于左侧(如果可能的话,头部向下),以保持呼吸道畅通,防止吸入。保持患者安静,维持正常体温。寻求医疗救助。 /毒物A和B/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 基本治疗:建立专利气道(如有需要,使用口咽或鼻咽气道)。如有必要,进行吸痰。观察呼吸不足的迹象,如有需要,辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿,如有必要,进行治疗……。监测休克,如有必要,进行治疗……。预防癫痫发作,如有必要,进行治疗……。对于眼睛污染,立即用水冲洗眼睛。在运输过程中,用0.9%的生理盐水(NS)持续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能吞咽、有强烈的干呕反射且不流口水,则用温水冲洗口腔,并给予5毫升/千克,最多200毫升的水进行稀释……。在去污后,用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
老鼠被喂食含有5.19%的阿洛拉红(Allura Red)的饮食。观察到0.1%和29%的完整染料分别通过尿液和粪便排出。在后续研究中,老鼠和狗每天预先非放射性阿洛拉红处理。随后,这些动物被给予35S标记的化合物,并研究了长达72小时的排泄和分布模式。两个物种对化合物的吸收有限,主要的排泄途径是通过粪便。在狗体内,72小时内92-95%的放射性出现在粪便中,而在老鼠体内,76-92%的放射性在这个时间内在粪便中出现。老鼠和狗尿液中色素的回收率分别变化在5.7和19.8%以及2.7和3.6%之间。在牺牲后,两个物种的肠道内容物中和老鼠洗过的肠道中发现了显著的放射性物质滞留。这被认为是由于化合物粘附在肠壁上,因为这些动物的整体和内脏含有少于0.4%的给药剂量。
Rats were fed a diet containing 5.19% of Allura Red. It was observed that 0.1% and 29% of the intact dye was excreted in the urine and feces respectively. In later studies, rats and dogs were pretreated daily with nonradioactive Allura Red. Subsequently, the animals were dosed with the 35S labelled compound and studied for up to 72 hours for excretion and distribution patterns of the color. Both species showed limited absorption of the compound with the major route of excretion being via the feces. In the dog 92-95% of the recovered radioactivity appeared in the feces within 72 hours while in the rat 76-92% of the recovered radioactivity appeared in the feces within this time period. Urinary recoveries of the color in rats and dogs, respectively varied between 5.7 and 19.8% and 2.7 and 3.6%. After sacrifice, significant retention of radioactivity was located in the intestinal contents of both species and in the washed intestines of the rats. This was thought to be due to adhesion of the compound to the intestinal wall, since the total carcass and viscera of these animals contained <0.4% of the administered dose.
来源:Hazardous Substances Data Bank (HSDB)

反应信息

  • 作为反应物:
    描述:
    (RS)-1-[2-(5-Bromo-benzofuran-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone 、 disodium;6-hydroxy-5-[(2-methoxy-5-methyl-4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate氰化亚铜 生成 (RS)-1-[2-(5-Cyano-benzofuran-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone
    参考文献:
    名称:
    N-AROYL CYCLIC AMINE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
    摘要:
    本发明涉及具有以下式子的N-芳酰基环状胺衍生物:其中变量如本文所定义,并且它们作为药物的用途,具体而言是作为促进睡眠的药物,特别是作为促进睡眠的药物。
    公开号:
    US20090012083A1
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文献信息

  • N-AROYL CYCLIC AMINE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
    申请人:BRANCH Clive Leslie
    公开号:US20080318944A1
    公开(公告)日:2008-12-25
    Disclosed are N-aroyl cyclic amine derivatives having the formula: where the variables are as define herein, and their use as pharmaceuticals, specifically as orexin receptor antagonists.
    本发明涉及具有以下公式的N-芳酰基环氨基衍生物:其中变量如本文所定义,并且它们作为药物的用途,特别是作为促进睡眠的药物。
  • N-aroyl cyclic amine derivatives as orexin receptor antagonists
    申请人:SmithKline Beecham Limited
    公开号:US07893090B2
    公开(公告)日:2011-02-22
    Disclosed are N-aroyl cyclic amine derivatives having the formula: where the variables are as define herein, and their use as pharmaceuticals, specifically as orexin receptor antagonists.
    本发明涉及一种具有以下式子的N-芳酰基环状胺衍生物: 其中变量如本文所定义,以及它们作为制药物的用途,特别是作为荷尔蒙受体拮抗剂。
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