Emetine hydrochloride

Modify Date: 2024-01-02 09:48:03

Emetine hydrochloride Structure
Emetine hydrochloride structure
Common Name Emetine hydrochloride
CAS Number 14198-59-5 Molecular Weight 517.100
Density 1.17g/cm3 Boiling Point 624.8ºC at 760 mmHg
Molecular Formula C29H41ClN2O4 Melting Point N/A
MSDS N/A Flash Point 331.7ºC

 Use of Emetine hydrochloride


Emetine hydrochloride, derived from the ipecac root, is a potent anti-protozoal and emetic agent. Emetine hydrochloride inhibits viral polymerases and inhibits Zika and Ebola virus infections. Emetine hydrochloride potently inhibits autophagy and has anti-malarial, anti-bacterial and anti-amoebic effect[1][2][3][4].

 Names

Name (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine,hydrochloride
Synonym More Synonyms

 Emetine hydrochloride Biological Activity

Description Emetine hydrochloride, derived from the ipecac root, is a potent anti-protozoal and emetic agent. Emetine hydrochloride inhibits viral polymerases and inhibits Zika and Ebola virus infections. Emetine hydrochloride potently inhibits autophagy and has anti-malarial, anti-bacterial and anti-amoebic effect[1][2][3][4].
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In Vitro Emetine hydrochloride accumulates SQSTM1 and MAP1LC3B in SNB-19 cells, indicating autophagy is blocked[1]. Emetine hydrochloride dose-dependently decreases NS1 protein level in HEK293 cells infected with the African prototype, ZIKV MR766 (IC50=52.9 nM). Emetine hydrochloride directly inhibits ZIKV NS5 RNA polymerase activity with an IC50 of 121 nM[1]. Cell Autophagy Assay[1] Cell Line: SNB-19 cells Concentration: 25, 50, 100, 200 nM Incubation Time: For 24 hours Result: Showed the accumulation of SQSTM1 and MAP1LC3B, indicating autophagy was blocked.
In Vivo Emetine hydrochloride (1, 2 mg/kg/day; IP; for 3 days) significantly reduces the serum viral load of ZIKV infected Ifnar1−/− mice[1]. Emetine hydrochloride (1 mg/kg/day; retro-orbital injection; for six days) reduces the levels of circulating ZIKV approximately 10-fold in three-month-old female SJL mice with ZIKVBR[1]. Emetine (0.002, 0.02, 0.2, 2 mg/kg/day; i.p.) not only attenuates blood glucose levels in dose-dependent way but also induces a persistent attenuation of blood glucose levels in C57Bl/6 male mice (20-25 g) [2]. Animal Model: Ifnar1−/− mice[1] Dosage: 1, 2 mg/kg Administration: IP; once daily for 3 days Result: Significantly reduced the serum viral load of ZIKV infected Ifnar1−/− mice.
References

[1]. Yang S, et al. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibitingviral replication and decreasing viral entry. Cell Discov. 2018 Jun 5;4:31.

[2]. Hudson LK, et al. Emetine Di-HCl attenuates Type 1 diabetes mellitus in mice. Mol Med. 2016 Jun 10;22

[3]. Matthews H, et al. Drug repositioning as a route to anti-malarial drug discovery: preliminary investigation of the in vitro anti-malarial efficacy of emetine dihydrochloride hydrate. Malar J. 2013 Oct 9;12:359.

[4]. Khandelwal N, et al. Emetine inhibits replication of RNA and DNA viruses without generating drug-resistant virusvariants. Antiviral Res. 2017 Aug;144:196-204.

[5]. Sands, M, et al. (1977). Antibacterial activity of emetine. Transactions of the Royal Society of Tropical Medicine and Hygiene, 71(5), 454-455.

 Chemical & Physical Properties

Density 1.17g/cm3
Boiling Point 624.8ºC at 760 mmHg
Molecular Formula C29H41ClN2O4
Molecular Weight 517.100
Flash Point 331.7ºC
Exact Mass 516.275513
PSA 52.19000
LogP 6.01210
Vapour Pressure 4.54E-16mmHg at 25°C

 Synonyms

(-)-Emetine hydrochloride
Cephaeline methyl ether HCl
6',7',10,11-Tetramethoxyemetan hydrochloride (1:1)
Cephaeline methyl ether hydrochloride
Emetin-hydrochlorid
EMETINE HYDROCHLORIDE
2H-Benzo[a]quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-, (2S,3R,11bS)-, hydrochloride (1:1)
Emetine monohydrochloride
Emetan, 6',7',10,11-tetramethoxy-, monohydrochloride
emetine chloride