Tiopronin 硫普罗宁

CAS 1953-02-2 MFCD00004861

化学结构图

1953-02-2
SMILES: CC(S)C(=O)NCC(=O)O

化学属性

Mol. FormulaC5H9NO3S
Mol. Weight163.19
Melting Point93-98°C
Appearance 50 白色结晶性粉末,有硫的臭味。溶于水。熔点95~97℃。急性毒性LD 小鼠(g/kg):2.1静脉注射。
Density1.294
SolubilitySoluble in DMSO (32 mg/ml at 25 °C), water (32 mg/ml at 25 °C), ethanol (32 mg/ml at 25 °C), and methanol.

别名和识别编码

Chemical NameTiopronin
CAS Number1953-02-2
Synonym Tiopronin {LY} Tiopronin {} {LY} Tiopronin {} {} {LY} Tiopronin {} {} {} {LY} Tiopronin {} {} {} {} {LY} Tiopronin {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Tiopronin
MDL NumberMFCD00004861
PubChem Substance ID5483
Beilstein Registry Number1859822
EC Number217-778-4
Reaxys-RN1859822
Merck Number9453
Chemical Name Translation硫普罗宁
Wiswesser Line NotationSHY1&1OM1VQ
LabNetwork Molecule IDLN01300535
InChIInChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
Canonical SMILESO=C(O)CNC(C(S)C)=O
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分类

  • Isotope Labelled Compounds
  • {SNA} Amino Acid Derivatives, Amino Acids, Chemical Biology, Chemical Synthesis,
  • Amino Acids & Derivatives
  • Sulfur & Selenium Compounds
  • {SNA} Amino Acid Derivatives, Amino Acids, Biochemicals and Reagents, Chemical B
  • {Chemicalbook} 药物: 消化系统用药: 肝病用药
  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, T, TF - TO, 分析/色谱
  • Pharmaceuticals
  • {SNA} Amino Acids, Amino Acids & Derivatives, Chemical Biology, Chemical Synthesis, Glycine, I - Z, Modified Amino Acids, Peptide Chemistry, 生化试剂
  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, T, TF - TO

产品应用

  • Controls the rate of cystine precipitation and excretion

相关文献及参考

  • Capasso, F., et al.: Agents Actions, 11, 741 (1981),
  • Amor, B., et al.: Arthritis Rheum., 25, 698 (1982),
  • Merck: 14,9453
  • Ichida, F., et al.: J. Int. Med. Res., 10, 325 (1982),

安全信息

GHS Symbol
Hazard statements
  • H302 Harmful if swallowed 吞食有害
WGK Germany3
RTECSMC0596500
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Signal word Warning
Hazard Codes Xn
Safety Statements
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P301+P312+P330
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1400 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia,
   Italy)  V.8-43 1953-88 For publisher information, see FRMCE8
   Volume(issue)/page/year: 41,758,1986

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 1800 mg/kg
TOXIC EFFECTS :
   Behavioral - excitement
   Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
   85JBAB "Proceedings of the International Symposium on Thiola, Tokyo, Japan,
   1970," Osaka, Japan, Santen Pharmaceutical Co., Ltd., 1970
   Volume(issue)/page/year: -,9,1970

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2330 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: 6,456,1982

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 673 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YKKZAJ Yakugaku Zasshi.  Journal of Pharmacy.  (Nippon Yakugakkai, 2-12-15
   Shibuya, Shibuya-ku, Tokyo 150, Japan)  No.1-    1881-
   Volume(issue)/page/year: 89,1138,1969

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERV

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 600 mg/kg
SEX/DURATION            : male 30 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
   Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland,
   accessory glands
   Reproductive - Paternal Effects - other effects on male
REFERENCE :
   IJEBA6 Indian Journal of Experimental Biology.  (Publications & Information
   Directorate, CSIR, Hillside Rd., New Delhi 110 012, India)  V.1-    1963-
   Volume(issue)/page/year: 24,34,1986

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1200 mg/kg
SEX/DURATION            : male 60 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
REFERENCE :
   CUSCAM Current Science.  (Current Science Assoc., Sadashivanagar P.O.,
   Bangalore 560 080, India) V.1-    1932-  Volume(issue)/page/year:
   55,378,1986

Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}

其他信息

  • 方法一:方法1:丙酸先用氯化亚砜氯化,再用溴+磷溴化,得α-溴丙酰氯(Ⅰ),收率84.7%。 甘氨酸溶于2mol/L氢氧化钠,用冰盐浴冷却,在剧烈搅拌下同时滴加化合物(Ⅰ)和2mol/L氢氧化钠溶液,保持溶液弱碱性。加毕,搅拌。盐酸酸化至Ph值1,用乙酸乙酯提取。提取液浓缩至有结晶析出,放置。滤集结晶,干燥,得化合物(Ⅱ),收率.53%。 硫化钠、升华硫和水,加热搅拌溶解备用。另外化合物(Ⅱ)和碳酸钠溶于水,滴加上述二硫化钠溶液。加毕,搅拌。用硫酸酸化至Ph值1,在搅拌下分批加入锌粉。加毕,搅拌。过滤,滤液减压浓缩至有结晶析出,放置。滤集结晶,用乙酸乙酯重结晶,真空干燥,得硫普罗宁,收率50.5%,熔点96~97.5℃。 方法2:甘氨酸、碳酸钠和水混合,在0℃以下同时滴加2-溴丙酰氯和10%碳酸钠溶液,保持弱碱性。加毕,搅拌。加入硫代苯甲酸,并滴加15%氢氧化钠溶液使之溶解。室温搅拌过夜,滤除少量不溶物,滤液酸化。滤集固体,依次用水、50%甲醇和乙酸乙酯洗,干燥,得化合物(Ⅳ),收率76.2%。 碳酸钠溶于水,加入化合物(Ⅳ),搅拌溶解后加入浓氨水,在20℃下搅拌过夜。滤除固体,用少量水洗。洗液和滤液合并,减压除氨,再用6mol/L盐酸酸化。减压浓缩,加入热的乙酸乙酯和乙醇(1:1)混合液溶解。滤除不溶物,滤液减压浓缩得油状物,冷却后析出固体,用乙酸乙酯重结晶,得硫普罗宁,产率54.9%,熔点95~97℃。 方法3:2-氯丙酸和氯化亚砜一起回流。蒸出过量的氯化亚砜,收集109~110℃的馏分,得2-氯丙酰氯,收率91%。 甘氨酸、碳酸钠和适量水混合,在冰盐浴冷却和剧烈搅拌下,同时滴加2-氯丙酰氯和碳酸钠的水溶液,保持弱碱性。加毕,搅拌。盐酸酸化至Ph值1,用乙酸乙酯提取,干燥,过滤,浓缩至有结晶析出,放置。滤集结晶,干燥得化合物(V),收率61%。 硫化钠九水合物、升华硫和适量水混合,加热搅拌至溶备用。另外,化合物(V)、碳酸钠和适量水混合,滴加制得的二硫化钠溶液。加毕,于40~45℃反应。用硫酸酸化至Ph值1,过滤。在搅拌下,往滤液中分批加入锌粉。加毕,搅拌。处理后得硫普罗宁,收率52.2%,熔点96~97.5℃。
  • 用途二:主要用于初期老年白内障,还可用于慢性肝炎、金属中毒、湿疹等。
  • MOL 文件:1953-02-2.mol
  • 硫普罗宁价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 T2614 硫普罗宁 Tiopronin 5G 713元 2014/06/02 T2614 硫普罗宁 Tiopronin 25G 1840元
  • 用途一:能赋活代谢酶,并能和阻碍HS-酶活性的有毒物质相螯合,因而有解毒作用。主要用于治疗急、慢性肝炎、肝硬化、酒精性肝损伤和药物引起的肝损伤,也可用于金属中毒、化疗及放疗保护、荨麻疹、皮炎、湿疹和痤疮等。
  • 上游原料:氧氯化硫 --> 硫磺 --> 甘氨酸 --> 丙酸 --> 丙酰氯 --> 二硫化钠 --> 丙酰溴 --> 2-溴丙酰氯 --> 硫代苯甲酸
  • MSDS 信息:alpha-Mercaptopropionyl glycine(1953-02-2).msds
  • 用途三:主要用于初期老年白内障,还可用于慢性肝炎;金属中毒;湿疹等。
  • Sigma Aldrich:1953-02-2(sigmaaldrich)

系列性分类


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