Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C29H40N2O4.2ClH.5H2O |
| Molecular Weight | 643.637 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.O.Cl.Cl.[H][C@]4(C[C@H]1C[C@]2([H])N(CCC3=CC(OC)=C(OC)C=C23)C[C@@H]1CC)NCCC5=CC(OC)=C(OC)C=C45
InChI
InChIKey=KRLFSNFHPJMYFW-ZICYJAKRSA-N
InChI=1S/C29H40N2O4.2ClH.5H2O/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24;;;;;;;/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3;2*1H;5*1H2/t18-,21-,24+,25-;;;;;;;/m0......./s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/international/emetine.html | https://www.ncbi.nlm.nih.gov/pubmed/11716514 | https://www.ncbi.nlm.nih.gov/pubmed/837444 | https://www.ncbi.nlm.nih.gov/pubmed/27912879
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/emetine.html | https://www.ncbi.nlm.nih.gov/pubmed/11716514 | https://www.ncbi.nlm.nih.gov/pubmed/837444 | https://www.ncbi.nlm.nih.gov/pubmed/27912879
Emetine is a principal alkaloid of ipecac, isolated from the ground roots of Uragoga ipecacuanha. Early use of emetine was in the form of oral administration of the extract of ipecac root, or ipecacuanha. This extract contains several, including cephaeline, and others. The identification of emetine as a more potent agent improved the treatment of amoebiasis. While the use of emetine still caused nausea, it was more effective than the crude extract of ipecac root. Additionally, emetine could be administered hypodermically which still produced nausea, but not to the degree experienced in oral administration. Emetine dihydrochloride hydrate is used in the laboratory to block protein synthesis in eukaryotic cells. It does this by binding to the 40S subunit of the ribosome. Emetine induces hypotension by blocking adrenoreceptors. Also, emetine was identified as a specific inhibitor of HIF-2α protein stability and transcriptional activity. Heavy or over usage of emetine can carry the risk of developing proximal myopathy and/or cardiomyopathy.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Cytopathological effects of protein synthesis inhibitor emetine on HeLa cells and their nucleoli]. | 2003 |
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| Emetine inhibits glycolysis in isolated, perfused rat hearts. | 2003 |
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| [Fascioliasis: diagnosis, epidemiology and treatment]. | 2003 Apr-Jun |
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| Cross-talk between the pathways leading to the induction of apoptosis and the secretion of tumor necrosis factor-alpha in ricin-treated RAW 264.7 cells. | 2003 Dec |
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| A role for dendritic protein synthesis in hippocampal late LTP. | 2003 Dec |
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| Transformation of ipecac (Cephaelis ipecacuanha) with Agrobacterium rhizogenes. | 2003 Nov |
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| Replication inhibitors modulate instability of an expanded trinucleotide repeat at the myotonic dystrophy type 1 disease locus in human cells. | 2003 Nov |
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| Marginal blebbing during the early stages of TNF-induced apoptosis indicates alteration in actomyosin contractility. | 2004 |
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| Inhibition of puromycin-induced apoptosis in breast cancer cells by IGF-I occurs simultaneously with increased protein synthesis. | 2004 |
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| 5-fluorouracil-induced oligodendrocyte death and inhibitory effect of cycloheximide, Trolox, and Z-VAD-FMK in murine cortical culture. | 2004 Apr 1 |
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| Cyclosporin A inhibits calcineurin (phosphatase 2B) and P-glycoprotein activity in Entamoeba histolytica. | 2004 Aug |
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| Histopathology of cutaneous amebiasis. | 2004 Aug |
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| In vitro activity of antiamoebic drugs against clinical isolates of Entamoeba histolytica and Entamoeba dispar. | 2004 Dec 21 |
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| Natural products for dental caries prevention. | 2004 Fall |
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| Increased calbindin-D28K immunoreactivity in rat cerebellar Purkinje cell with excitatory amino acids agonists is not dependent on protein synthesis. | 2004 Feb |
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| Transcriptional regulation of TNF family receptors and Bcl-2 family by chemotherapeutic agents in murine CT26 cells. | 2004 Feb 1 |
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| The nonclassical MHC class I molecule Qa-1 forms unstable peptide complexes. | 2004 Feb 1 |
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| Manipulation of nonsense mediated decay identifies gene mutations in colon cancer Cells with microsatellite instability. | 2004 Jan 22 |
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| Mutation in mitochondrial complex I ND6 subunit is associated with defective response to hypoxia in human glioma cells. | 2004 Jul 12 |
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| Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoquinolizidine alkaloid by using a domino process. | 2004 Jun 7 |
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| Emetine ditartrate: a possible lead for emergency contraception. | 2004 May |
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| From mRNA to tumor suppressor. | 2004 Sep |
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| Nonsense-mediated decay microarray analysis identifies mutations of EPHB2 in human prostate cancer. | 2004 Sep |
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| The type IV-specific phosphodiesterase inhibitor rolipram and its effect on hippocampal long-term potentiation and synaptic tagging. | 2004 Sep 1 |
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| NMD microarray analysis for rapid genome-wide screen of mutated genes in cancer. | 2005 |
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| Investigations of the protein synthesis dependency of mGluR-induced long-term depression in the dentate gyrus of freely moving rats. | 2005 |
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| Myxobacterial epothilones and tubulysins as promising anticancer agents. | 2005 |
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| Inactivation of MAP kinase signalling in Myc transformed cells and rescue by LiCl inhibition of GSK3. | 2005 Apr 5 |
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| Dynamic acetylation of all lysine 4-methylated histone H3 in the mouse nucleus: analysis at c-fos and c-jun. | 2005 Dec |
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| GATA4, 5 and 6 mediate TGFbeta maintenance of endodermal gene expression in Xenopus embryos. | 2005 Feb |
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| Activity-dependent long-term potentiation of intrinsic excitability in hippocampal CA1 pyramidal neurons. | 2005 Feb 16 |
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| Persistent phosphorylation by protein kinase Mzeta maintains late-phase long-term potentiation. | 2005 Feb 23 |
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| Entamoeba histolytica: cloning and expression of the poly(A) polymerase EhPAP. | 2005 Jul |
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| Entamoeba histolytica EhPgp5 transcriptional activation depends on putative emetine response elements. | 2005 Jul |
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| Terpenoid tetrahydroisoquinoline alkaloids emetine, klugine, and isocephaeline inhibit the activation of hypoxia-inducible factor-1 in breast tumor cells. | 2005 Jun |
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| Ribotoxic stress response to the trichothecene deoxynivalenol in the macrophage involves the SRC family kinase Hck. | 2005 Jun |
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| Spontaneous recovery from extinction depends on the reconsolidation of the acquisition memory in an appetitive learning paradigm in the honeybee (Apis mellifera). | 2005 May 4 |
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| Long-distance apoptotic killing of cells is mediated by hydrogen peroxide in a mitochondrial ROS-dependent fashion. | 2005 Nov |
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| Ipecac syrup abuse, morbidity, and mortality: isn't it time to repeal its over-the-counter status? | 2005 Sep |
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| Identification of inactivating mutations in the JAK1, SYNJ2, and CLPTM1 genes in prostate cancer cells using inhibition of nonsense-mediated decay and microarray analysis. | 2005 Sep |
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| Anisomycin activates p38 MAP kinase to induce LTD in mouse primary visual cortex. | 2006 Apr 26 |
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| Suppression of galactosylceramidase (GALC) expression in the twitcher mouse model of globoid cell leukodystrophy (GLD) is caused by nonsense-mediated mRNA decay (NMD). | 2006 Aug |
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| In vitro susceptibility of Entamoeba histolytica and Giardia lamblia to plants used in Mexican traditional medicine for the treatment of gastrointestinal disorders. | 2006 Dec 6 |
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| Antigiardial activity of methanolic extracts from Helianthemum glomeratum Lag. and Rubus coriifolius Focke in suckling mice CD-1. | 2006 Dec 6 |
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| Targeting heat shock response to sensitize cancer cells to proteasome and Hsp90 inhibitors. | 2006 Feb 1 |
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| State of nucleolar proteins B23/nucleophosmin and UBF in HeLa cells during apoptosis induced by tumor necrosis factor. | 2006 Jun |
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| p38 Mitogen-activated protein kinase mediates IL-8 induction by the ribotoxin deoxynivalenol in human monocytes. | 2006 Jun 15 |
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| Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step. | 2006 Mar 30 |
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| Reduction of cytotoxicity of the alkaloid emetine through P-glycoprotein (MDR1/ABCB1) in human Caco-2 cells and leukemia cell lines. | 2006 Oct |
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| Persistent (>24h) long-term depression in the dentate gyrus of freely moving rats is not dependent on activation of NMDA receptors, L-type voltage-gated calcium channels or protein synthesis. | 2007 Jan |
Patents
Sample Use Guides
Subcutaneous or intramuscular, 60mg daily, For 10 Days
Route of Administration:
Other
T. b. brucei TC 221 were used to activity evaluation. A cell density of 1.3 ×10 6 cells/ml was exposed to different doses of homohar- ringtonine (0.01, 0.25 and 1 μM) and emetine (0.02, 0.25 and 2 μM) for short periods of time (30, 120 and 240 min). Cells were then centrifuged at 1800 ×g for 5 min at room temperature, washed two times with sterile phosphate-buffered saline (PBS) and transferred to fresh, drug-free Baltz medium at a density of 10 4 cells/ml. The cell density was determined every 24 h in the improved Neubauer counting chamber. Growth recovery was monitored for 72 h after drug contact.
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100000076113
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DTXSID50229608
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79300-07-5
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7083-71-8
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07DUY5KO8X
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SUB11931MIG
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EMETINE HYDROCHLORIDE PENTAHYDRATE
Created by
admin on Fri Dec 15 18:54:18 GMT 2023 , Edited by admin on Fri Dec 15 18:54:18 GMT 2023
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PRIMARY | Chemical name: Emetine dihydrochloride pentahydrate; 6',7',10,11-tetramethoxyemetan dihydrochloride pentahydrate; CAS Reg. No. 79300-07-5 (pentahydrate). Description: A white or very slightly yellow, crystalline powder; odourless.Solubility: Freely soluble in water and ethanol (~750 g/l) TS. Category: Antiamoebic drug. Storage: Emetine hydrochloride should be kept in a tightly closed container, protected from light.Labelling: The designation on the container of Emetine hydrochloride should state whether the substance is the pentahydrate or the heptahydrate. |
ACTIVE MOIETY
SUBSTANCE RECORD
