Page last updated: 2024-12-05

dimetridazole

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

Description

Dimetridazole is a nitroimidazole derivative that has been used as an antiprotozoal drug. It is effective against a variety of protozoal infections, including giardiasis, trichomoniasis, and amebiasis. Dimetridazole is synthesized by a multi-step process that involves the reaction of 2-nitroimidazole with 1,3-dichloro-2-propanol. Dimetridazole works by inhibiting the growth and replication of protozoa. It is believed to do this by interfering with the synthesis of DNA. Dimetridazole is still being studied for its potential use in the treatment of other infections. For example, some studies have shown that dimetridazole may be effective against certain bacteria, including Staphylococcus aureus. However, dimetridazole has been associated with a number of side effects, including nausea, vomiting, and diarrhea. It is also known to cause liver damage in some cases. Dimetridazole is not currently approved for use in humans in the United States. However, it is still used in some countries for the treatment of protozoal infections.'

Dimetridazole: A compound used to treat histomoniasis in poultry. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dimetridazole : A C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by methyl groups. An antiprotozoal drug, it has been banned by both the Government of Canada and the European Union as a livestock feed additive owing to suspicions of it being carcinogenic. [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 CID3090
CHEMBL ID38938
CHEBI ID141155
SCHEMBL ID63278
MeSH IDM0006468

Synonyms (90)

Synonym
AC-12771
5-23-05-00058 (beilstein handbook reference)
unii-k59p7xnb8x
k59p7xnb8x ,
rp 8595
wln: t5n cnj a1 b1 enw
5-nitro-1,2-dimethylimidazole
1,2-dimethyl-5-nitroimidazole
dimetridazole
imidazole,2-dimethyl-5-nitro-
dimetridazol
nsc-226253
1h-imidazole,2-dimethyl-5-nitro-
component of emtryl
8595 r.p.
emtryl
unizole soluble
emtrymix
emtrylvet
1,2-dimethyl-5-nitro-1h-imidazole
nsc 226253
ccris 997
dimetridazolo [dcit]
dimetridazole [inn:ban]
ai3-27217
dimetridazol [inn-spanish]
dimetridazolum [inn-latin]
imidazole, 1,2-dimethyl-5-nitro-
einecs 209-001-2
caswell no. 371a
brn 0130665
epa pesticide chemical code 371200
EU-0033396
1,2-dimethyl-5-nitro-imidazole
551-92-8
nsc226253
1h-imidazole, 1,2-dimethyl-5-nitro-
rp-8595
alazol
CHEMBL38938
dimetridazole (inn)
alazol [veterinary] (tn)
D07855
FT-0667567
D1564
dimetridazolum
CHEBI:141155
AKOS000121461
NCGC00249084-01
dtxsid5020497 ,
cas-551-92-8
NCGC00256615-01
dtxcid30497
tox21_302989
tox21_201618
NCGC00259167-01
A830512
D4081
STL259130
dimetridazolo
FT-0606425
dimetridazole [mart.]
dimetridazole [inn]
dimetridazole [mi]
S5541
SCHEMBL63278
BBL028012
NCGC00249084-02
tox21_113657
CS-4956
AM87060
W-205401
W-105582
dimetrizadole
HY-B1244
mfcd00047046
1, 2-dimethyl-5-nitroimidazole
SR-01000944778-1
sr-01000944778
dimetridazole, vetranal(tm), analytical standard
Q5277356
EN300-21183
CCG-266155
D78134
551-92-8 (free base)
dimetridazole free base
(1r,3s)-(-)-camphoricanhydride
1,2-dimethyl-5-nitroimidazole; dimetridazole; 1,2-dimethyl-5-nitro-1h-imidazole
dimetridazole 1000 microg/ml in acetonitrile
Z104493616

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Treatment with dimetridazole controlled the clinical disease but did not eliminate the infection."( Hexamitiasis in a laboratory mouse colony.
Flatt, RE; Halvorsen, JA; Kemp, RL, 1978
)
0.6

Bioavailability

ExcerptReferenceRelevance
" Bioavailability (F > 80%) and some pharmacokinetic parameters were determined."( Tissue concentration of dimetridazole in laying hens.
Biernacki, B; Niedzielska, J; Posyniak, A; Semeniuk, S; Zmudzki, J,
)
0.44
" The absolute bioavailability of the tablet in fasted pigeons was 83."( Pharmacokinetics and anti-trichomonal efficacy of a dimetridazole tablet and water-soluble powder in homing pigeons (Columba livia).
DeBacker, P; Inghelbrecht, S; Remon, JP; Ronsmans, S; Vercruysse, J; Vermeersch, H, 1996
)
0.54

Dosage Studied

Laying hens were dosed orally with dimetridazole (DMZ) for 3 days or intramuscularly (50 mg/kg) residues were determined by liquid chromatography in albumen and yolk.

ExcerptRelevanceReference
" It was a 5-fold increase of the recommended ronidazole dosage which eliminated the infection in affected pigeons."( In vitro nitroimidazole resistance of Trichomonas gallinae and successful therapy with an increased dosage of ronidazole in racing pigeons (Columba livia domestica).
Franssen, FF; Lumeij, JT, 1992
)
0.28
"Laying hens were dosed orally with dimetridazole (DMZ) (50 and 250 mg/kg) for 3 days or intramuscularly (50 mg/kg), also for 3 days, and the residues were determined by liquid chromatography in albumen and yolk."( Residues of dimetridazole in eggs after treatment of laying hens.
Biernacki, B; Niedzielska, J; Posyniak, A; Semeniuk, S; Zmudzki, J, 1996
)
0.95
"After laying hens had been dosed orally with dimetridazole (DMZ) for 3 days (50 and 250 mg/kg body weight (b."( Tissue concentration of dimetridazole in laying hens.
Biernacki, B; Niedzielska, J; Posyniak, A; Semeniuk, S; Zmudzki, J,
)
0.7
" In aerobic conditions, MZ and DZ produced significant dose-response relationships."( Evaluation of the genotoxic activity of metronidazole and dimetridazole in human lymphocytes by the comet assay.
Castegnaro, M; De Méo, MP; Duménil, G; Guiraud, H; Laget, M; Ré, JL; Vanelle, P, 1997
)
0.54
" Only by increasing the dosage of antibiotics to a therapeutic level does antibiotic metaphylaxis surpass homeopathic metaphylaxis."( Homeopathy versus antibiotics in metaphylaxis of infectious diseases: a clinical study in pig fattening and its significance to consumers.
Albrecht, H; Schütte, A, 1999
)
0.3
" The routine antibiotic dosage of metaphylaxis is too low to be effective."( Homeopathy versus antibiotics in metaphylaxis of infectious diseases: a clinical study in pig fattening and its significance to consumers.
Albrecht, H; Schütte, A, 1999
)
0.3
" Results obtained showed that, at appropriate concentrations, H(2)O(2) accelerates MNZ degradation by generating additional HO(); however, when the dosage of H(2)O(2) exceeds the optimal concentration, the efficacy of MNZ degradation is reduced."( Gamma irradiation of pharmaceutical compounds, nitroimidazoles, as a new alternative for water treatment.
Ferro-García, MA; López-Peñalver, J; Prados-Joya, G; Rivera-Utrilla, J; Sánchez-Polo, M, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antiprotozoal drugAny antimicrobial drug which is used to treat or prevent protozoal infections.
antiparasitic agentA substance used to treat or prevent parasitic infections.
[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 (2)

ClassDescription
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
[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]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency26.11660.006038.004119,952.5996AID1159521; AID1159523
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency44.31420.003041.611522,387.1992AID1159552; AID1159555
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (45)

Assay IDTitleYearJournalArticle
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID211142The Mutagenicity against Trichomonas foetus relative to Ronidazole.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles.
AID416736Ratio of number of revertant per nmol of drug for Salmonella Typhimurium YG1042 to number of revertant per nmol of drug for Salmonella Typhimurium TA1002009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID318681Anticarcinogenic activity in rat assessed as induction of tumors per day2008Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6
QSAR modeling of the rodent carcinogenicity of nitrocompounds.
AID235834Safety index.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles.
AID416729Cytotoxicity against human THP1 cells after 72 hrs by propidium iodide-based flow cytometry2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416734Induction of mutagenicity in Salmonella Typhimurium TA100 assessed as number of revertant per nmol after 48 hrs relative to metranidazole2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416733Induction of mutagenicity in Salmonella Typhimurium TA100 assessed as number of revertant per nmol after 48 hrs2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416735Induction of mutagenicity in Salmonella Typhimurium YG1042 assessed as number of revertant per nmol after 48 hrs relative to metranidazole2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416728Specificity index, ratio of IC50 for human THP1 cells to IC50 for Trichomonas vaginalis TVR872009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID211139In vitro anti-trichomonal activity against Trichomonas foetus-Ortho strain-2.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structural alterations that differentially affect the mutagenic and antitrichomonal activities of 5-nitroimidazoles.
AID416730Induction of mutagenicity in Salmonella Typhimurium YG1042 assessed as number of revertant per ug after 48 hrs2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416731Induction of mutagenicity in Salmonella Typhimurium TA100 assessed as number of revertant per ug after 48 hrs2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416732Induction of mutagenicity in Salmonella Typhimurium YG1042 assessed as number of revertant per nmol after 48 hrs2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
AID416727Antitrichomonas activity against Trichomonas vaginalis TVR87 after 48 hrs by trypan blue staining2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Lowering of 5-nitroimidazole's mutagenicity: towards optimal antiparasitic pharmacophore.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (120)

TimeframeStudies, This Drug (%)All Drugs %
pre-199047 (39.17)18.7374
1990's28 (23.33)18.2507
2000's20 (16.67)29.6817
2010's14 (11.67)24.3611
2020's11 (9.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.07

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 Index40.07 (24.57)
Research Supply Index4.93 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index62.87 (26.88)
Search Engine Supply Index2.13 (0.95)

This Compound (40.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.48%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (2.22%)4.05%
Observational0 (0.00%)0.25%
Other130 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]