依託咪酯

**依託咪酯**
	(R)-etomidate ethyl ester
臨床資料
商品名（英語：Drug nomenclature）	Amidate, Hypnomidate, Tomvi
AHFS/Drugs.com	Monograph
核准狀況	美 DailyMed: Etomidate;
給藥途徑	靜脈注射
ATC碼	N01AX07 (WHO) ;
法律規範狀態
法律規範	澳：限醫生處方（S4）; 加：處方藥（℞-only）; 中：處方藥（第二類精神藥品）; 英：處方藥（℞-only） (POM); 美：處方藥（℞-only）;
藥物動力學數據
血漿蛋白結合率	76%
藥物代謝	在血漿和肝臟中發生酯水解
生物半衰期	75 分鐘
排泄途徑	尿液(85%)，膽管 (15%)
識別資訊
	IUPAC命名法 Ethyl 3-[(1R)-1-phenylethyl]imidazole-5-carboxylate; ;
CAS號	33125-97-2
PubChem CID	36339;
DrugBank	DB00292 ;
ChemSpider	33418 ;
UNII	Z22628B598;
KEGG	D00548 ;
ChEMBL	ChEMBL23731 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID5023033 ;
ECHA InfoCard	100.046.700
化學資訊
化學式	C14H16N2O2
摩爾質量	244.29 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
熔點	67 °C（153 °F）
沸點	392 °C（738 °F）
	SMILES O=C(OCC)c1cncn1C(c2ccccc2)C;
	InChI 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 ; Key:NPUKDXXFDDZOKR-UHFFFAOYSA-N ;

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

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-苯基乙醇的Mitsunobu偶合反應^[3]及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]；它和丙醇鈉或異丙醇鈉反應，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

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

^ 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）.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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
^ 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.
^ 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].
^ 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

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

[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].

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]