Emetine
- CAS No.
- 483-18-1
- Chemical Name:
- Emetine
- Synonyms
- C09421;EMetin;EMETINE;Emetine (>Ipecac alkali;EMetine (>90%);EMETINE USP/EP/BP;Emetine HCL BP/USP;Cephaeline methyl ether;6',7',10,11-Tetramethoxymetan
- CBNumber:
- CB6512352
- Molecular Formula:
- C29H40N2O4
- Molecular Weight:
- 480.64
- MOL File:
- 483-18-1.mol
- Modify Date:
- 2023/7/17 14:24:23
| Melting point | 89-96°C |
|---|---|
| alpha | D20 -50° (c = 2 in CHCl3) |
| Boiling point | 578.63°C (rough estimate) |
| Density | 1.1174 (rough estimate) |
| refractive index | 1.5800 (estimate) |
| storage temp. | -20°C Freezer |
| solubility | Soluble in Water (100 mg/ml) |
| form | solid |
| pka | 5.77, 6.64(at 25℃) |
| color | White |
| Water Solubility | 961.3mg/L(15 ºC) |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in water may be stored at -20°C for up to 3 months. |
SAFETY
Risk and Safety Statements
| RIDADR | 1544 |
|---|---|
| HazardClass | 6.1(b) |
| PackingGroup | III |
| Toxicity | LD50 i.p. in rats: 12.1 mg/kg (Radomski) |
Emetine Chemical Properties,Uses,Production
Chemical Properties
Brown Solid
Uses
Emetine is the principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha.
Indications
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.
Definition
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.
World Health Organization (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.
Hazard
Toxic by ingestion.
Health Hazard
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.
Mechanism of action
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.
References
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
Emetine Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | China | 24639 | 58 | Inquiry |
| TargetMol Chemicals Inc. | +1-781-999-5354 | United States | 19973 | 58 | Inquiry |
| GIHI CHEMICALS CO.,LIMITED | +8618058761490 | China | 49999 | 58 | Inquiry |
| Wuhan Huangzhen Biochemical Co., Ltd | 13795480948 13795480948 | China | 4958 | 58 | Inquiry |
| Chengdu Alfa Biotechnology Co.,Ltd. | 028-028-85142057 19983342022 | China | 1984 | 58 | Inquiry |
| Shaanxi DIDU pharmaceutical and Chemical Co., Ltd | 17691182729 18161915376 | China | 10011 | 58 | Inquiry |
| RENI Pharmaceutical Technology Co., Ltd | 028-87865381 18108190480 | China | 3302 | 58 | Inquiry |
| Hubei CuiRan Biotechnology Co., Ltd. | 181-86211184 18162791556 | China | 4351 | 58 | Inquiry |
| Aikon International Limited | 18626450290 | China | 10718 | 58 | Inquiry |
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