130929-57-6

• 常用中文名：恩他卡朋
• 常用英文名：Entacapone
• CAS号：130929-57-6
• 分子式：C₁₄H₁₅N₃O₅
• 分子量：305.286
• 相关类别： 原料药 神经系统用药 脑代谢调节药
• 发布时间：2018-09-16 16:50:30
• 更新时间：2024-01-02 13:24:06
• 【用途一】
  为COMT抑制剂，用于治疗帕金森病。

名称

• 中文名: 恩他卡朋
• 英文名: entacapone
• 中文别名: (2E)-2-氰基-3-(3,4-二羟基-5-硝基苯基)-N,N-二乙基-2-丙烯酰胺; (E)-2-氰基-3-(3,4二羟基-5-硝基苯)-N,N二乙基丙烯酰胺; 安托卡朋 F·S; 安托卡朋; (E)-2-氰基-3-(3,4-二羟基-5-硝基苯基)-N,N-二乙基-2-丙烯酰胺
• 英文别名: (E)-2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide; (2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide; Comtan; Comtes; (2Z)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide; OR-611; 2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide; MFCD00866580; 2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2E)-; (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; Comtess; (E)-a-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide; Entacapone; 2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2Z)-

物化性质

• 密度: 1.4±0.1 g/cm3
• 沸点: 526.6±50.0 °C at 760 mmHg
• 熔点: 162-1630C
• 分子式: C₁₄H₁₅N₃O₅
• 分子量: 305.286
• 闪点: 272.3±30.1 °C
• 精确质量: 305.101166
• PSA: 130.38000
• LogP: 2.38
• 外观性状: 黄色粉末
• 蒸汽压: 0.0±1.4 mmHg at 25°C
• 折射率: 1.642
• 储存条件: -20°C Freezer
• 分子结构:

  1、 摩尔折射率：79.12

  2、 摩尔体积（cm³/mol）：219.2

  3、 等张比容（90.2K）：629.8

  4、 表面张力（dyne/cm）：68.1

  5、 极化率（10-24cm3）：31.36

• 计算化学:

  1.疏水参数计算参考值（XlogP）:2.1

  2.氢键供体数量:2

  3.氢键受体数量:6

  4.可旋转化学键数量:4

  5.互变异构体数量:16

  6.拓扑分子极性表面积130

  7.重原子数量:22

  8.表面电荷:0

  9.复杂度:500

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:1

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：结晶。

  2.熔点：162~163℃。

生物活性

• 描述: Entacapone是特异的外周活性的邻苯二酚-O-甲基转移酶(COMT)抑制剂,IC50为151 nM。
• 相关类别:
  信号通路 >> 代谢酶/蛋白酶 >> COMT
  信号通路 >> 神经信号通路 >> COMT
  研究领域 >> 神经疾病
• 参考文献:

  [1]. Piccini P, Brooks DJ, Korpela K, The catechol-O-methyltransferase(COMT) inhibitor entacapone enhances the pharmacokinetic and clinical response to Sinemet CR in Parkinson's disease. J Neurol Neurosurg Psychiatry. 2000 May;68(5):589-94.

  [2]. Di Giovanni S, Eleuteri S, Paleologou KE, Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity. J Biol Chem. 2010 May 14;285(20):1494

  [3]. Sethi KD, Hauser RA, Isaacson SH, Levodopa/carbidopa/entacapone 200/50/200 mg (Stalevo 200) in the treatment of Parkinson's disease: a case series. Cases J. 2009 Jul 30;2:7134.

  [4]. Poulopoulos M, Waters C. Carbidopa/levodopa/entacapone: the evidence for its place in the treatment of Parkinson's disease. Core Evid. 2010 Jul 27;5:1-10.

MSDS

Material Safety Data Sheet Section1. Identification of the substance Product Name: Entacapone Synonyms: Section2. Hazards identification Harmful by inhalation, in contact with skin, and if swallowed. Section3. Composition/information on ingredients. Ingredient name:Entacapone CAS number:130929-57-6 Section4. First aid measures Skin contact:Immediately wash skin with copious amounts of water for at least 15 minutes while removing contaminated clothing and shoes. If irritation persists, seek medical attention. Eye contact:Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical attention. Inhalation:Remove to fresh air. In severe cases or if symptoms persist, seek medical attention. Ingestion:Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention. Section5. Fire fighting measures In the event of a fire involving this material, alone or in combination with other materials, use dry powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus should be worn. Section6. Accidental release measures Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national standards. Respiratory precaution:Wear approved mask/respirator Hand precaution:Wear suitable gloves/gauntlets Skin protection:Wear suitable protective clothing Eye protection:Wear suitable eye protection Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container for disposal. See section 12. Environmental precautions: Do not allow material to enter drains or water courses. Section7. Handling and storage Handling:This product should be handled only by, or under the close supervision of, those properly qualified in the handling and use of potentially hazardous chemicals, who should take into account the fire, health and chemical hazard data given on this sheet. Store in closed vessels, refrigerated. Storage: Section8. Exposure Controls / Personal protection Engineering Controls: Use only in a chemical fume hood. Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles. General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse. Section9. Physical and chemical properties Appearance:Not specified Boiling point:No data No data Melting point: Flash point:No data Density:No data Molecular formula:C14H15N3O5 Molecular weight:305.3 Section10. Stability and reactivity Conditions to avoid: Heat, flames and sparks. Materials to avoid: Oxidizing agents. Possible hazardous combustion products: Carbon monoxide, nitrogen oxides. Section11. Toxicological information No data. Section12. Ecological information No data. Section13. Disposal consideration Arrange disposal as special waste, by licensed disposal company, in consultation with local waste disposal authority, in accordance with national and regional regulations. Section14. Transportation information Non-harzardous for air and ground transportation. Section15. Regulatory information No chemicals in this material are subject to the reporting requirements of SARA Title III, Section 302, or have known CAS numbers that exceed the threshold reporting levels established by SARA Title III, Section 313. SECTION 16 - ADDITIONAL INFORMATION N/A

安全

• 危害码 (欧洲): Xn,T,F
• 风险声明 (欧洲): R10:Flammable. R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R37/38:Irritating to respiratory system and skin . R41:Risk of serious damage to eyes. R62:Possible risk of impaired fertility. R38:Irritating to the skin. R36/37/38:Ir
• 安全声明 (欧洲): S26-S36-S39-S45-S36/37/39-S16
• 危险品运输编码: UN 1986 3/PG 3
• WGK德国: 1
• RTECS号: KM5250000
• 包装等级: III
• 危险类别: 3
• 海关编码: 2942000000

合成路线

制备

1.83g 3,4-二羟基-5-硝基苯甲醛和1.5g N,N-二乙基氰基乙酰胺和催化量的哌啶乙酸盐溶于40ml干燥乙醇中,搅拌过夜,得2.23g粗品,收率73%,熔点153～156℃.

2. 在90℃下加热,将3.0kg粗品溶于含80gHBr(或40gHCl)的8.0kg乙酸(或甲酸)中.缓慢冷却到20℃,并在此温度搅拌20h,然后在15℃搅拌6h.过滤收集析出的结晶,先小心地用冷的(4℃)1L甲苯-乙酸(1:lv/v)的混合液洗,再用1L的冷甲苯洗.在真空和45℃下干燥,得2.4kg结晶性的纯的恩他卡朋,收率80％,mp162~163℃.

海关

海关编码	2942000000