Page last updated: 2024-12-06

ipronidazole

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

Description

Ipronidazole is a nitroimidazole derivative with antiprotozoal and antibacterial properties. It acts by interfering with DNA synthesis in susceptible organisms. Ipronidazole has been studied for its potential use in treating various infections, including giardiasis, trichomoniasis, and amebiasis. Its synthesis involves a multi-step process that starts with the condensation of 2-nitro-5-chloroimidazole with a suitable alkylating agent. Ipronidazole is studied due to its broad-spectrum activity against anaerobic bacteria and protozoa, and its potential for the treatment of infections that are resistant to other drugs. Its importance lies in its therapeutic applications and its potential for the development of new anti-infective agents.'

Ipronidazole: An antihistomonal agent with low toxicity. It also promotes growth and feed utilization in poultry. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID26951
CHEMBL ID334786
CHEBI ID181451
SCHEMBL ID159633
MeSH IDM0011705

Synonyms (57)

Synonym
CHEBI:181451
1-methyl-5-nitro-2-propan-2-ylimidazole
2-isopropyl-1-methyl-5-nitro-imidazole
5-(hydroxy(oxido)amino)-2-isopropyl-1-methyl-1h-imidazole
ipronidazolo [dcit]
ipronidazolum [inn-latin]
1-methyl-2-(1-methylethyl)-5-nitro-1h-imidazole
einecs 238-957-3
brn 0744577
ipronidazol [inn-spanish]
nsc 109212
NCGC00181095-01
ipronidazole (usan/inn)
D04608
ipropran
ipronidazole
1h-imidazole, 1-methyl-2-(1-methylethyl)-5-nitro-
imidazole, 2-isopropyl-1-methyl-5-nitro-
m+b 16905
2-isopropyl-1-methyl-5-nitroimidazole
nsc109212
nsc-109212
ro 07-1554
ro 7-1554
14885-29-1
1h-imidazole, 2-isopropyl-1-methyl-5-nitro-
inchi=1/c7h11n3o2/c1-5(2)7-8-4-6(9(7)3)10(11)12/h4-5h,1-3h
ro-7-1554
CHEMBL334786
ro-71554
1-methyl-2-isopropyl-5-nitroimidazole
NCGC00181095-02
AKOS006271453
unii-045bu63e23
045bu63e23 ,
ipronidazolum
ipronidazolo
ipronidazol
ipronidazole [usan:inn:ban]
dtxcid5026839
cas-14885-29-1
tox21_112711
dtxsid7046839 ,
FT-0670410
ipronidazole [inn]
ipronidazole [green book]
ipronidazole [mi]
ipronidazole [usan]
ipronidazole [mart.]
SCHEMBL159633
2-isopropyl-1-methyl-5-nitro-1h-imidazole #
ipronidazole, vetranal(tm), analytical standard
J-008524
2-isopropyl-1-methyl-5-nitro-1h-imidazole
Q6065435
1-methyl-5-nitro-2-(propan-2-yl)-1h-imidazole
2-isopropyl-1-methyl-5- nitroimidazole

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Medicated swine given dosage of 25 mg/L of drinking water had greater frequency of nonhemorrhagic and hemorrhagic diarrhea than did those given the higher concentrations, and diarrhea in some swine did not subside during medication."( Ipronidazole in the drinking water for treatment and prevention of experimental swine dysentery.
Olson, LD, 1977
)
1.7
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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)
AR proteinHomo sapiens (human)Potency10.68220.000221.22318,912.5098AID743036
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.07560.000229.305416,493.5996AID743075
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay IDTitleYearJournalArticle
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.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID23681Partition coefficient (logP)1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID172616The amount of the unchanged form of compound detected in the urine samples collected at 0-18 hr after the treatment by HPLC technique1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID26535Capacity factor (log k')1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID16041Percent biliary excretion property by administering intravenously to rats was reported as amount of unchanged form of compound detected in bile samples collected at 0-6 hr after the treatment.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID16037Percent biliary excretion property by administering intravenously to rats was reported as amount of unchanged form of compound detected in bile samples collected at 0-2 hr after the treatment.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID172618The amount of unchanged compound detected in urine collected at 0-18 hr after treatment1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID194145The total 54 h urinary excretion of unchanged compound reported as log (percent X 10) of the administered dose1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID172622The amount of unchanged compound in urine collected at 0-72 h after treatment1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID23240Partition coefficient (logP)1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID194146The total 72 hr urinary excretion of unchanged compound reported as log (percent X 10) of the administered dose1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID16036Percent biliary excretion property by administering intravenously to rats was reported as amount of unchanged form of compound detected in bile samples collected at 0-1 hr after the treatment.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID16039Percent biliary excretion property by administering intravenously to rats was reported as amount of unchanged form of compound detected in bile samples collected at 0-4 hr after the treatment.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID172621The amount of unchanged compound in urine collected at 0-54 hr after treatment1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID16040Percent biliary excretion property by administering intravenously to rats was reported as amount of unchanged form of compound detected in bile samples collected at 0-5 hr after the treatment.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID194141The total 18 hr urinary excretion of the unchanged form of compound in urine was reported as log (percent X 10) of the administered dose by HPLC technique1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID16038Percent biliary excretion property by administering intravenously to rats was reported as amount of unchanged form of compound detected in bile samples collected at 0-3 hr after the treatment.1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
The influence of physicochemical parameters on the biliary excretion of a series of nitroimidazoles.
AID172620The amount of unchanged compound in urine collected at 0-36 hr after treatment1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID194143The total 18 hr urinary excretion of unchanged compound reported as log (percent X 10) of the administered dose1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
AID194144The total 36 hr urinary excretion of unchanged compound reported as log (percent X 10) of the administered dose1986Journal of medicinal chemistry, Apr, Volume: 29, Issue:4
Relationship between lipophilic character and urinary excretion of nitroimidazoles and nitrothiazoles in rats.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-199020 (68.97)18.7374
1990's2 (6.90)18.2507
2000's3 (10.34)29.6817
2010's2 (6.90)24.3611
2020's2 (6.90)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.30

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.30 (24.57)
Research Supply Index3.61 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]