Disodium;4-[(2-oxido-6-sulfonaphthalen-1-yl)diazenyl]benzenesulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Disodium;4-[(2-oxido-6-sulfonaphthalen-1-yl)diazenyl]benzenesulfonate
• 英文别名: disodium;4-[(2-oxido-6-sulfonaphthalen-1-yl)diazenyl]benzenesulfonate
• 化学式: C16H10N2Na2O7S2
• 分子量: 452.4
• InChiKey: OIQPTROHQCGFEF-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -3.22
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  9

ADMET

代谢

当将颜色口服给大鼠时...未吸收的主要被肠道细菌还原，并以磺胺酸和1-氨基-2-羟基-6-萘磺酸的形式通过尿液排出。...兔在口服给药后以n-乙酰磺胺酸作为代谢物...

When color is given orally to rats... unabsorbed was mainly reduced by intestinal bacteria and excreted as sulfanilic acid and 1-amino-2-hydroxy-6-naphthalenesulfonic acid in urine. ...n-Acetylsulfanilic acid as metabolite in rabbits after oral administration...

来源:Hazardous Substances Data Bank (HSDB)

代谢

日落黄FCF在体外很容易被大鼠肠道和盲肠中的细菌还原。它与血清蛋白结合。

Sunset yellow FCF is easily reduced in vitro by bacteria present in intestine and cecum of rats. It binds with serum proteins.

来源:Hazardous Substances Data Bank (HSDB)

代谢

4...磺化偶氮染料（苋菜红、日落黄、新胭脂红和柠檬黄）的无氧还原作用已经通过将分离自人类粪便和大鼠肠内容物的细菌悬浮液与染料进行孵育来研究，染料浓度为50微摩尔，在pH值为4的磷酸盐缓冲液中，以氮气作为气相。来自5名男性志愿者的粪便菌群将这4种染料的平均还原速率分别为38.4、25.1、18.2和6.5纳米摩尔/毫克/蛋白质/小时。尽管年龄、日常饮食和生活环境存在较大差异，但不同个体来源的细菌悬浮液对每种染料的还原速率几乎没有差异。...大鼠肠道菌群对苋菜红和日落黄的还原速率是人类粪便菌群的4-5倍，但在新胭脂红和柠檬黄的还原速率上，这两种类型的细菌悬浮液之间没有显著差异。...

The anaerobic reduction of 4... sulfonated azo dyes, amaranth, sunset yellow, new coccine and tartrazine, has been studied by incubating bacterial suspensions isolated from human feces and from the intestinal contents of rats with 50 um concentrations of the dyes in phosphate buffer pH 4 /with/ nitrogen as the gaseous phase. Human fecal flora from 5 male volunteers reduced the 4 dyes at mean rates of 38.4, 25.1, 18.2 and 6.5 nmol/mg/protein/hr, respectively. For each dye, there was little difference in the reduction rates effected by the bacterial suspensions from the different individuals in spite of considerable divergence in age, daily diets and living circumstances. ...The rates of amaranth and sunset yellow reduction by rat gut flora were 4-5 times higher than those by human fecal flora, but there was no significant difference between the two types of bacterial suspension in the reduction rates for new coccine and tartrazine. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

当兔子每千克体重喂食0.5克该色素后，48小时内的尿液中可以检测到以下代谢物：日落黄（2%），磺胺酸（54%），对乙酰胺基苯磺酸（23%），1-氨基-2-萘酚-6-磺酸（55%在24小时内）……尿液中的代谢物主要是通过偶氮键的还原裂解产生的产品。肝脏中减少偶氮键的酶在代谢中作用很小。因此，肠道细菌还原色素是最有可能产生芳香胺和氨基磺酸的方式；这些物质然后部分被肠道吸收。

When rabbits were fed 0.5 g/kg bw of the color, the following metabolites could be identified in 48 hours urine: sunset yellow (2%), sulfanilic acid (54%), p-acetamido benzene-sulfonic acid (23%), 1-amino-2-naphthol-6-sulfonic acid (55% in 24 hours). ... The metabolites in the urine were predominantly products resulting from the reductive fission of the azolinkage. The liver enzyme that reduces azolinkages plays little part in metabolism. Reduction of the color by the intestinal bacteria is therefore the most probable way to aromatic amines and aminosulfonic acids; these are then partly absorbed by the intestinal tract.

来源:Hazardous Substances Data Bank (HSDB)

代谢

6-羟基-5-(苯基偶氮)-2-萘磺酸钠盐（SS-AN），这是食品黄色5号[日落黄FCF，6-羟基-5-(4-磺酸苯基偶氮)-2-萘磺酸的钠盐]中的一种次要颜色，通过口服给予Sprague-Dawley大鼠。在大鼠尿液中检测到了代谢物A、代谢物B以及未改变的SS-AN作为有色的代谢物。化学结构的分析表明，代谢物A（主要峰）是6-羟基-5-(4-磺酸氧苯基偶氮)-2-萘磺酸，即SS-AN的硫酸共轭物，而代谢物B（次要峰）是6-羟基-5-(4-羟基苯基偶氮)-2-萘磺酸（SS-PAP），这是代谢物A去除了硫酸的衍生物。...口服给予的SS-AN在24小时尿液样本中被代谢成无色代谢物（对氨基酚45.3%，邻氨基酚9.4%，苯胺0.4%）。对有色代谢物的分析...表明代谢物A（0.29%）、SS-PAP（0.01%）和SS-AN（0.02%）在24小时尿液样本中被检测到。大约56%的SS-AN被排入尿液中，其余的可能被排入粪便中。

The sodium salt of 6-hydroxy-5-(phenylazo)-2-naphthalenesulfonic acid (SS-AN), which is a subsidiary color present in Food Yellow No. 5 [Sunset Yellow FCF, disodium salt of 6-hydroxy-5-(4-sulfophenylazo)-2-naphthalenesulfonic acid], was orally administered to Sprague-Dawley rats. Metabolite A, metabolite B, and unaltered SS-AN were detected as colored metabolites in the rat urine. Analysis of the chemical structures showed that metabolite A (major peak) was 6-hydroxy-5-(4-sulfooxyphenylazo)-2-naphthalenesulfonic acid, the sulfuric acid conjugate of SS-AN, and metabolite B (minor peak) was 6-hydroxy-5-(4-hydroxyphenylazo)-2-naphthalenesulfonic acid (SS-PAP), which is a derivative of metabolite A without the sulfuric acid. ...The orally administered SS-AN had been metabolized to the colorless metabolites (p-aminophenol 45.3%, o-aminophenol 9.4%, aniline 0.4%) in the 24-hr urine samples. Analysis of the colored metabolites... indicated the presence of metabolite A (0.29%), SS-PAP (0.01%), and SS-AN (0.02%) were detected in the 24-hr urine samples. Approximately 56% of SS-AN was excreted into the urine and the rest is probably excreted into feces.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：日落黄FCF

IARC Carcinogenic Agent:Sunset Yellow FCF

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论集：第8卷：（1975年）一些芳香偶氮化合物

IARC Monographs:Volume 8: (1975) Some Aromatic Azo Compounds

来源:International Agency for Research on Cancer (IARC)

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)

吸收、分配和排泄

当将颜色口服给大鼠时，有3%被吸收并在尿液中以及胆汁中以未改变的形式排出：因此在肝脏中减少的很少。...在大鼠静脉注射后，有20-30%通过胆汁排出。

When color is given orally to rats, 3% is absorbed and excreted unchanged in urine and in bile: thus little is reduced in liver. ...After its iv injection in rats, 20-30% was excreted in bile.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

...在首次给药后的前24小时内，有1.5%的未改变的单体染料通过尿液和胆汁排出。在给予聚合物衍生物后，没有未改变的染料被吸收。在给予日落黄及其聚合物衍生物的动物中，偶氮键断裂产物1-氨基-2-萘酚-6-磺酸的被吸收率分别为8.5%和6.9%，而断裂产物磺胺甲苯酸的被吸收率分别为37.4%和0%。...

... A trace to 1.5 percent of unchanged monomeric dyes was excreted in urine and bile during the first 24 hr after dosing. No unchanged dye was absorbed after administration of the polymeric derivatives. In animals dosed with sunset yellow and its polymer derivative, absorption of the azo-bound cleavage product 1-amino-2-naphthol-6-sulphonic acid was 8.5 and 6.9 percent, respectively, while absorption of the cleavage product sulphanilic acid was 37.4 and 0 percent, respectively. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在5只动物中给予14C-日落黄（2.7毫克，4.62微居里）后，96小时内的放射性物质通过尿液排出的量为剂量的8.5 +/- 3.4%。从日落黄染的大鼠24小时尿液收集物中，含有40%的磺胺酸摩尔当量。24小时尿液中完整的染料代表剂量的1-2%。粪便中的放射性物质排出高峰出现在第一个24小时内。放射性物质的回收率为94.5 +/- 5.7%。放射性物质的总回收率为103 +/- 3.3%。

In 5 animals dosed with 14C-sunset yellow (2.7 mg, 4.62 uCi) after 96 hours urinary excretion of radioactivity was 8.5 +/- 3.4% of the dose. The 24 hours urine collection from the sunset yellow rats contained 40% of the molar equivalents of sulfanilic acid. Intact dye in the 24 hours urine represented 1-2% of the dose. Peak fecal excretion occurred during the first 24 hours. The recovery of radioactivity was 94.5 +/- 5.7%. Total recovery of radioactivity was 103 +/- 3.3%.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

14只老鼠在2-25毫克的范围内服用了日落黄，在72小时内分别通过尿液和胆汁排泄了0.3%和1.5%的给药染料，以及尿液中37%的磺胺酸当量。

Fourteen rats were dosed with sunset yellow within the range of 2-25 mg and within 72 hours excreted 0.3 and 1.5% of the administered dye in urine and bile respectively and 37% of the sulfanilic acid equivalents in the urine.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  Disodium;4-[(2-oxido-6-sulfonaphthalen-1-yl)diazenyl]benzenesulfonate 、 6-{[4-(6-fluoro-2-methyl-5-quinolinyl)-1-piperazinyl]acetyl}-4-methyl-2H-1,4-benzoxazine-3(4H)-one 生成 6-{2-[4-(6-fluoro-2-methyl-5-quinolinyl)-1-piperazinyl]-1-hydroxyethyl}-4-methyl-2H-1,4-benzoxazine-3(4H)-one
  参考文献：
  名称：

  Benzoxazinone derivatives, preparation thereof and uses in the treatment of cns and other disorders

  摘要：

  公开了化学式（I）的化合物及其药学上可接受的盐：其中A、R1、R2、R3、p、q、A和X的定义如规范中所述。还公开了这些化合物的制备方法以及在治疗中枢神经系统和其他疾病，包括抑郁和焦虑症方面的用途。

  公开号：

  US20060264429A1

文献信息

• Vasopressin V1a Antagonists
  申请人：Batt Andrzej Roman

  公开号：US20090029965A1

  公开（公告）日：2009-01-29

  The present invention concerns compounds inter alia according to general formula 1 a . Compounds according to the invention are vasopressin V 1a receptor antagonists. Pharmaceutical compositions of the compounds are useful as treatment of dysmenorrhoea.

  本发明涉及一些化合物，其中包括一般式1a所示的化合物。根据本发明的化合物是抗利尿激素V1a受体拮抗剂。该化合物的制药组合物可用于治疗痛经。
• VASOPRESSIN V1A ANTAGONISTS
  申请人：BATT ANDRZEJ ROMAN

  公开号：US20120101082A1

  公开（公告）日：2012-04-26

  The present invention concerns compounds inter alia according to general formula 1a. Compounds according to the invention are vasopressin V 1a receptor antagonists. Pharmaceutical compositions of the compounds are useful as treatment of dysmenorrhoea.

  本发明涉及一些化合物，其中包括通用式1a。本发明的化合物是加压素V1A受体拮抗剂。该化合物的药物组成物可用于治疗痛经。
• Vasopressin V1a antagonists
  申请人：Vantia Limited

  公开号：US08202858B2

  公开（公告）日：2012-06-19

  The present invention concerns compounds inter alia according to general formula 1a. Compounds according to the invention are vasopressin V1a receptor antagonists. Pharmaceutical compositions of the compounds are useful as treatment of dysmenorrhoea.

  本发明涉及一些通式1a的化合物。根据本发明的化合物是加压素V1a受体拮抗剂。所述化合物的药物组合物可用于治疗痛经。

表征谱图