エメチン

エメチン 化学特性,用途語,生産方法

• 解説

  エメチン，白色の粉末．融点74 ℃．[α]²⁰_D－50°(クロロホルム)．エタノール，エーテル，アセトン，クロロホルムに易溶，水，石油エーテルに難溶．副アルカロイドのセファエリン(融点115～116 ℃．[α]_D－43°)がエメチンとともに得られる．LD50 17 mg/kg(ラット，経口)．
  

  森北出版「化学辞典（第2版）
  

• 用途

  アメーバ赤痢の特効薬．催吐，去たん薬としても使われる．

• 製法

  アカネ科Cephaelis ipecacuanhaの地下根から得られる吐根(とこん)アルカロイドの一つ．

• 化学的特性

  Brown Solid

• 使用

  Emetine is the principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha.

• 定義

  ChEBI: Emetine is a pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties. It has a role as an antiprotozoal drug, a plant metabolite, an antiviral agent, an emetic, a protein synthesis inhibitor, an antimalarial, an antineoplastic agent, an autophagy inhibitor, an antiinfective agent, an expectorant, an anticoronaviral agent and an antiamoebic agent. It is a pyridoisoquinoline and an isoquinoline alkaloid. It is functionally related to a cephaeline. It is a conjugate base of an emetine(2+). It derives from a hydride of an emetan.

• 適応症

  Chlorprothixene (Taractan) has been reported twice to be effective in the treatment of PHN. For severe pain, an initial 50 to 100 mg IM injection has been advocated. Otherwise, the dosage is 25 to 50 mg PO q6h. The recommended duration of therapy is 4 to 10 days. Higher doses are unwarranted and frequently result in side effects.

• 世界保健機関（WHO）

  Emetine, an alkaloid obtained from ipecacuanha, was first used rationally as an amoebocide in 1912. It was subsequently widely used and was included in earlier editions of the WHO Model List of Essential Drugs but has now been replaced by the less cardiotoxic synthetic derivative dehydroemetine. Although it is valuable in the treatment of systemic amoebic hepatitis it has now been largely superseded by considerably less toxic drugs, and in particular by metronidazole.

• 危険性

  Toxic by ingestion.

• 健康ハザード

  The toxicity of cephaeline is lower than thatof emetine. The toxic effects are cumulative. Ingestion of high doses may producehypotension, muscle weakness, and gastroin testinal problems, including nausea, vomit ing, and diarrhea.

• 作用機序

  This drug has a direct amebicidal effect against trophozoites E. histolytica in tissues, and it is not active against cysts in either the lumen or intestinal walls, or in other organs. The mechanism of action of emetine consists of the blockage of protein synthesis in eukaryotic (but not in prokaryotic) cells. It inhibits the process of polypeptide chain formation. Protein synthesis is inhibited in parasite and mammalian cells, but not in bacteria.
  Emetine is currently only used as a drug for treating amebiasis in cases of resistance to other drugs. Synonyms of this drug are ipecin and methylcefalin.

• 参考文献

  1) Lee et al. (2008), Ipecacuanha: the South American vomiting root; J R Coll. Physicians Edinb., 38 355
  2) Sun et al. (2019), Emetine Exhibits Anticancer Activity in Breast Cancer Cells as an Antagonist of Wnt/β-catenin Signaling; Oncol. Rep., 42 1735 DOI:10.3892/or.2019.7290
  3) Yang et al. (2018), Changing cancer survival in China during 2003-2015: a pooled analysis of 17 population-based cancer registries; Cell Discov., 4 31
  4) Choy et al. (2020), Remdesivir, Lopinavir, and Homoharringtonine Inhibit SARS-CoV-2 Replication in Vitro; Antivir. Res., 178 104786 DOI:10.1016/j.antiviral.2020.104786
  5) Cuyas et al. (2015), Anti-protozoal and Anti-Bacterial Antibiotics That Inhibit Protein Synthesis Kill Cancer Subtypes Enriched for Stem Cell-Like Properties; Cell Cycle, 14 3527
  DOI:10.1080/15384101.2015.1044173
  6) Application of emetine in SARS-CoV-2 treatment: regulation of p38 MAPK signaling pathway for preventing emetine-induced cardiac complications DOI:10.1080/15384101.2022.2100575
  7) Emetine, a potent alkaloid for the treatment of SARS-CoV-2 targeting papain-like protease and non-structural proteins: pharmacokinetics, molecular docking and dynamic studies DOI:10.1080/07391102.2021.1946715
  8) A Comprehensive Guide to the Hazardous Properties of Chemical Substances
  9) Manual of Dermatologic Therapeutics with Essentials of Diagnosis, 7th Edition
  10) Consolidated List of Products whose Consumption

エメチン 生産企業

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