142217-69-4

• 常用中文名：恩替卡韦
• 常用英文名：Entecavir
• CAS号：142217-69-4
• 分子式：C₁₂H₁₅N₅O₃
• 分子量：277.279
• 相关类别： 原料药 人工合成抗感染类药 抗病毒类药
• 发布时间：2018-02-08 08:00:00
• 更新时间：2024-01-02 08:07:22
• Entecavir(SQ 34676; BMS 200475)是有选择且有效地HBV抑制剂。在HepG2细胞中的EC50值为3.75 nM。
• 本品为鸟嘌呤核苷类似物，对乙肝病毒（HBV）多聚酶具有抑制作用。它能够通过磷酸化成为具有活性的三磷酸盐，三磷酸盐在细胞内的半衰期为15小时。通过与HBV多聚酶的天然底物三磷酸脱氧鸟嘌呤核苷竞争，恩替卡韦三磷酸盐能抑制病毒多聚酶（逆转录酶）的所有三种活性：（1）HBV多聚酶的启动；（2）前基因组mRNA逆转录负链的形成；（3）HBV DNA正链的合成。恩替卡韦三磷酸盐对HBV DNA多聚酶的抑制常数(Ki)为0.0012μM。恩替卡韦三磷酸盐对细胞的α、β、δDNA多聚酶和线粒体γDNA多聚酶抑制作用较弱，Ki值为18至于160μM。

名称

• 中文名: 恩替卡韦
• 英文名: entecavir (anhydrous)
• 中文别名: ENTECAVIR(一水合物); 2-氨基-9-((1S,3R,4S)-4-羟基-3-(羟甲基)-2-甲烯基环戊基)-3H-嘌呤-6(9H)-酮; 9-(4-羟基-3-羟甲基-2-亚甲基环戊-1-基)鸟嘌呤
• 英文别名: 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one; entecavir (anhydrous); 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one; 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-; Baraclude; entecavir; 9H-purin-6-ol, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-; UNII-NNU2O4609D; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-9H-purin-6-ol

物化性质

• 密度: 1.8±0.1 g/cm3
• 沸点: 734.2ºC at 760 mmHg
• 熔点: 249-252ºC
• 分子式: C₁₂H₁₅N₅O₃
• 分子量: 277.279
• 闪点: 397.9ºC
• 精确质量: 277.117493
• PSA: 130.05000
• LogP: -0.96
• 外观性状: 白色至灰白色/黄色结晶粉末
• 折射率: 1.837
• 储存条件: -20°C Freezer

生物活性

• 描述: Entecavir(SQ 34676; BMS 200475)是有选择且有效地HBV抑制剂。在HepG2细胞中的EC50值为3.75 nM。
• 相关类别:
  信号通路 >> 抗感染 >> HBV
  研究领域 >> 感染
• 靶点:

  EC50: 3.75 nM (anti-HBV, HepG2 cell)[2]

• 体外研究: BMS-200475对HBV的EC50为3.75 nM。将其掺入HBV的蛋白质引物中,随后抑制逆转录酶的引发步骤。 BMS-200475的抗病毒活性明显低于其他RNA和DNA病毒[1]。与其他脱氧鸟苷类似物(喷昔洛韦,更昔洛韦,lobucavir和阿昔洛韦)或拉米夫定相比,恩替卡韦更容易被磷酸化为其活性代谢物。恩替卡韦的细胞内半衰期为15小时[2]。
• 体内研究: BMS-200475每日口服治疗,剂量范围为0.02至0.5毫克/千克体重,持续1至3个月,可有效降低慢性感染土拨鼠中土拨鼠肝炎病毒(WHV)病毒血症的水平[3]。
• 细胞实验: BMS 200475在磷酸盐缓冲盐水（PBS）中制备，并用含有2％胎牛血清的适当培养基稀释。将HepG2 2.2.15细胞以每孔5×10 5个细胞的密度接种在12孔Biocoat胶原包被的平板上，并保持在融合状态2至3天，然后用1mL掺有BMS 200475的培养基覆盖。 HBV的定量在第10天进行[1]。
• 参考文献:

  [1]. Innaimo SF, et al. Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. Antimicrob Agents Chemother. 1997 Jul;41(7):1444-9.

  [2]. Rivkin A, et al. A review of entecavir in the treatment of chronic hepatitis B infection. Curr Med Res Opin. 2005 Nov;21(11):1845-57.

  [3]. Genovesi EV, et al. Efficacy of the carbocyclic 2'-deoxyguanosine nucleoside BMS-200475 in the woodchuck model of hepatitis B virus infection. Antimicrob Agents Chemother. 1998 Dec;42(12):3209-18.

MSDS

Material Safety Data Sheet Section1. Identification of the substance Product Name: Entecavir Synonyms: Section2. Hazards identification Harmful by inhalation, in contact with skin, and if swallowed. Section3. Composition/information on ingredients. Ingredient name:Entecavir CAS number:142217-69-4 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. Storage:Store in closed vessels, refrigerated. 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 Melting point:No data Flash point:No data Density:No data Molecular formula: C12H15N5O3 Molecular weight: 277.3 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

• 危险品运输编码: NONH for all modes of transport
• 海关编码: 2933990090

合成路线

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海关

海关编码	2933990090
中文概述	2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%