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依託咪酯

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依託咪酯
(R)-etomidate ethyl ester
臨床資料
商品名英語Drug nomenclatureAmidate, Hypnomidate, Tomvi
AHFS/Drugs.comMonograph
核准狀況
給藥途徑靜脈注射
ATC碼
法律規範狀態
法律規範
藥物動力學數據
血漿蛋白結合率76%
藥物代謝血漿肝臟中發生酯水解
生物半衰期75 分鐘
排泄途徑尿液(85%),膽管 (15%)
識別資訊
  • Ethyl 3-[(1R)-1-phenylethyl]imidazole-5-carboxylate
CAS號33125-97-2  checkY
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.046.700 編輯維基數據鏈接
化學資訊
化學式C14H16N2O2
摩爾質量244.29 g·mol−1
3D模型(JSmol英語JSmol
熔點67 °C(153 °F)
沸點392 °C(738 °F)
  • O=C(OCC)c1cncn1C(c2ccccc2)C
  • InChI=1S/C14H16N2O2/c1-3-18-14(17)13-9-15-10-16(13)11(2)12-7-5-4-6-8-12/h4-11H,3H2,1-2H3 checkY
  • Key:NPUKDXXFDDZOKR-UHFFFAOYSA-N checkY

依託咪酯(英語:etomidate),別名R-(+)-1-(1-苯乙基)-1-氫-咪唑-5-甲酸乙酯(R)-(+)-1-(1-苯乙基)-1-氫-咪唑-5-甲酸乙酯(R)-1-(1-苯基乙基)-1H-咪唑-5-甲酸乙酯乙苄咪唑。是一種催眠劑,用於誘導全身麻醉。

化學性質[編輯]

1-苯乙基咪唑-5-甲醇的氧化-酯化反應[2]、咪唑-5-甲酸乙酯和1-苯基乙醇Mitsunobu偶合反應[3]N-[1-(2-溴苯基)乙基]甘氨酸乙酯的成環-脫溴反應可用於該藥物的合成。[4]

它在氫氧化鈉溶液中水解,酸化後可以得到(R)-1-(1-苯乙基)咪唑-5-甲酸[5];它和丙醇鈉異丙醇鈉反應,可以得到相應的丙酯或異丙酯類似物。[6]它可以和釕形成配合物。[7]

管制信息[編輯]

依託咪酯在中國是麻醉類處方藥,非法販賣涉及妨害藥品管理罪和販賣毒品罪。[8]吸食含有依託咪酯的電子煙則會被強制戒毒。[9]

參考文獻[編輯]

  1. ^ Summary Basis of Decision (SBD) for Tomvi. Health Canada. 23 October 2014 [29 May 2022]. (原始內容存檔於2022-05-30). 
  2. ^ Marcus Baumann, Ian R. Baxendale. A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives. European Journal of Organic Chemistry, 2017. doi:10.1002/ejoc.201700833.
  3. ^ Joydev K. Laha and Gregory D. Cuny. Synthesis of Fused Imidazoles, Pyrroles, and Indoles with a Defined Stereocenter α to Nitrogen Utilizing Mitsunobu Alkylation Followed by Palladium-Catalyzed Cyclization. J. Org. Chem. 2011, 76, 20, 8477–8482. doi:10.1021/jo201237h.
  4. ^ Cor G. M. Janssen, Jos B. A. Thijssen, Willy L. M. Verluyten, Jozef J. P. Heykants. Synthesis of (R)-(+)-3H-etomidate. Journal of Labelled Compounds and Radiopharmaceuticals, 1987. 24 (8). doi:10.1002/jlcr.2580240805.
  5. ^ Zhao, Shizhen; et al. Design, synthesis and evaluation of 1-benzyl-1H-imidazole-5-carboxamide derivatives as potent TGR5 agonists. Bioorganic & Medicinal Chemistry. 2021. 32. 115972. doi:10.1016/j.bmc.2020.115972.
  6. ^ Zolle, Ilse M.; et al. New Selective Inhibitors of Steroid 11β-Hydroxylation in the Adrenal Cortex. Synthesis and Structure-Activity Relationship of Potent Etomidate Analogues. Journal of Medicinal Chemistry (2008), 51(7), 2244-2253. doi:10.1021/jm800012w
  7. ^ Ana Zamora; et al. Ruthenium-containing P450 inhibitors for dual enzyme inhibition and DNA damage. Dalton Trans., 2017,46, 2165-2173. doi:10.1039/C6DT04405K.
  8. ^ 又一种“上头电子烟”!添加了依托咪酯,危害不亚于毒品. 紹興市公安局. 2023-07-24 [2024-06-27]. 
  9. ^ 3名未成年人抽电子烟抽进戒毒所. 新浪網. 2024-06-26 [2024-06-27]. 

外部連結[編輯]

  • Etomidate. Drug Information Portal. U.S. National Library of Medicine. [2022-06-23]. (原始內容存檔於2022-08-01).