依托咪酯

**依托咪酯**
	(R)-etomidate ethyl ester
临床资料
商品名（英语：Drug nomenclature）	Amidate, Hypnomidate, Tomvi
AHFS/Drugs.com	Monograph
核准状况	美 DailyMed: Etomidate;
给药途径	静脉注射
ATC码	N01AX07 (WHO) ;
法律规范状态
法律规范	澳：限医生处方（S4）; 加：处方药（℞-only）; 中：处方药（第二类精神药品）; 英：处方药（℞-only） (POM); 美：处方药（℞-only）;
药物动力学数据
血浆蛋白结合率	76%
药物代谢	在血浆和肝脏中发生酯水解
生物半衰期	75 分钟
排泄途径	尿液(85%)，胆管 (15%)
识别信息
	IUPAC命名法 Ethyl 3-[(1R)-1-phenylethyl]imidazole-5-carboxylate; ;
CAS号	33125-97-2
PubChem CID	36339;
DrugBank	DB00292 ;
ChemSpider	33418 ;
UNII	Z22628B598;
KEGG	D00548 ;
ChEMBL	ChEMBL23731 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID5023033 ;
ECHA InfoCard	100.046.700
化学信息
化学式	C14H16N2O2
摩尔质量	244.29 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
熔点	67 °C（153 °F）
沸点	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 ;

依托咪酯（英语：etomidate），别名R-(+)-1-(1-苯乙基)-1-氢-咪唑-5-甲酸乙酯、(R)-(+)-1-(1-苯乙基)-1-氢-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。是一种催眠剂，用于诱导全身麻醉。

化学性质[编辑]

1-苯乙基咪唑-5-甲醇的氧化-酯化反应^[2]、咪唑-5-甲酸乙酯和1-苯基乙醇的Mitsunobu偶合反应^[3]及N-[1-(2-溴苯基)乙基]甘氨酸乙酯的成环-脱溴反应可用于该药物的合成。^[4]

它在氢氧化钠溶液中水解，酸化后可以得到(R)-1-(1-苯乙基)咪唑-5-甲酸^[5]；它和丙醇钠或异丙醇钠反应，可以得到相应的丙酯或异丙酯类似物。^[6]它可以和钌形成配合物。^[7]

管制信息[编辑]

依托咪酯在中国是麻醉类处方药，非法贩卖涉及妨害药品管理罪和贩卖毒品罪。^[8]吸食含有依托咪酯的电子烟则会被强制戒毒。^[9]

参考文献[编辑]

^ Summary Basis of Decision (SBD) for Tomvi. Health Canada. 23 October 2014 [29 May 2022]. （原始内容存档于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. 绍兴市公安局. 2023-07-24 [2024-06-27].
^ 3名未成年人抽电子烟抽进戒毒所. 新浪网. 2024-06-26 [2024-06-27].

外部链接[编辑]

Etomidate. Drug Information Portal. U.S. National Library of Medicine. [2022-06-23]. （原始内容存档于2022-08-01）.

[1] Summary Basis of Decision (SBD) for Tomvi. Health Canada. 23 October 2014 [29 May 2022]. （原始内容存档于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. 绍兴市公安局. 2023-07-24 [2024-06-27].

[9] 3名未成年人抽电子烟抽进戒毒所. 新浪网. 2024-06-26 [2024-06-27].

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