Page last updated: 2024-12-06

dehydroemetine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Dehydroemetine is a naturally occurring alkaloid derived from the ipecacuanha plant (Carapichea ipecacuanha). It exhibits significant anti-amoebic activity and has been used in the treatment of amoebiasis, an infection caused by the parasite Entamoeba histolytica. Dehydroemetine's anti-amoebic properties are attributed to its ability to inhibit the growth and replication of amoeba. Dehydroemetine has been studied for its potential therapeutic applications in treating amoebiasis, particularly in cases resistant to other anti-amoebic drugs. However, its clinical use is limited due to its toxicity, which can include cardiovascular effects and hepatotoxicity. Research efforts are ongoing to investigate potential modifications to the structure of dehydroemetine that could reduce its toxicity while maintaining its anti-amoebic efficacy.'

dehydroemetine: was MH 1991-94 (see under EMETINE 1976-90); use EMETINE to search DEHYDROEMETINE 1976-94; amebicide, derivative of emetine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dehydroemetine : A pyridoisoquinoline which was developed in response to the cardiovascular toxicity associated with emetine and results from the dehydrogenation of the heterotricylic ring of emetine. It is an antiprotozoal agent and displays antimalarial, antiamoebic, and antileishmanial properties. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID21022
CHEMBL ID1697741
CHEBI ID149634
CHEBI ID4363
SCHEMBL ID66089
MeSH IDM0229928

Synonyms (61)

Synonym
nsc-129414
dehydroemetinum
ro 1-9334/19
mebadin
bt 436
emetine,3-didehydro-
nsc131546
(-)-2,3-dehydroemetine
dehidroemetina
emetine,3-dehydro-, (-)-
emetan,3-didehydro-6',7',10,11-tetramethoxy-
nsc-131546
2-dehydroemetine
ccris 4110
nsc 131546
einecs 225-542-7
dehydroemetine [inn:ban:dcf]
3-ethyl-9,10-dimethoxy-1,6,7,11b-tetrahydro-2-((1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl)-4h-benzo(a)quinolizine
dehidroemetina [inn-spanish]
dehydroemetinum [inn-latin]
2,3-didehydro-6',7',10,11-tetramethoxyemetan
(11bs)-2-[[(1r)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-4,6,7,11b-tetrahydro-1h-benzo[a]quinolizine
dehydroemetine
C07996
4914-30-1
mebadin (tn)
dehydroemetine (inn)
D00828
NCI60_000664
SR-02000000202-1
CHEBI:149634
ro-1933419
chebi:4363 ,
CHEMBL1697741
7s79qt1t91 ,
unii-7s79qt1t91
1986-67-0
unii-l36ly97uh4
dehydroemetine, (+/-)-
4h-benzo(a)quinolizine, 3-ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-(((1r)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl)methyl)-, (11bs)-rel-
l36ly97uh4 ,
(+/-)-2,3-dehydroemetine
26266-12-6
emetane, didehydro-6',7',10,11-tetramethoxy-
didehydro-6',7',10,11-tetramethoxyemetane
121523-30-6
4h-benzo(a)quinolizine, 3-ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-(((1r)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl)methyl)-, (11bs)-
(11bs)-3-ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-(((1r)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl)methyl)-4h-benzo(a)quinolizine
ro-1-9334/19
dehydroemetine [mi]
dehydroemetine [who-dd]
dehydroemetine [inn]
SCHEMBL66089
Q5252386
HY-121241
DB13865
CS-0081294
MS-28899
4h-benzo[a]quinolizine,3-ethyl-1,6,7,11b-tetrahydro-9,10-dimethoxy-2-[[(1r)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-, (11bs)-
DTXSID901023600
AKOS040741621
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antiprotozoal drugAny antimicrobial drug which is used to treat or prevent protozoal infections.
antimalarialA drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antileishmanial agentAn antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
pyridoisoquinolineAn organic heterotricyclic compound with a skeleton derived from a pyridine ring fused to an isoquinoline.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID588211Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in humans2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID588213Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in non-rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID588212Literature-mined compound from Fourches et al multi-species drug-induced liver injury (DILI) dataset, effect in rodents2010Chemical research in toxicology, Jan, Volume: 23, Issue:1
Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (71.79)18.7374
1990's7 (17.95)18.2507
2000's2 (5.13)29.6817
2010's1 (2.56)24.3611
2020's1 (2.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.87

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.87 (24.57)
Research Supply Index3.89 (2.92)
Research Growth Index4.01 (4.65)
Search Engine Demand Index54.33 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (4.35%)5.53%
Reviews2 (4.35%)6.00%
Case Studies4 (8.70%)4.05%
Observational0 (0.00%)0.25%
Other38 (82.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]