Page last updated: 2024-12-06

4-nitroimidazole

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

Description

4-nitroimidazole is a heterocyclic compound with a nitro group at the 4-position. It is a key intermediate in the synthesis of various pharmaceuticals, including metronidazole, a potent antimicrobial drug effective against anaerobic bacteria. Its synthesis typically involves nitration of imidazole using a mixture of nitric acid and sulfuric acid. Research on 4-nitroimidazole focuses on its role in drug development, exploring its antimicrobial activity and potential for use in treating parasitic infections. The presence of the nitro group imparts a unique electronic structure and contributes to the compound's biological activity. Studies investigate its interactions with biological systems and its potential for modifying the structure of existing drugs to enhance their efficacy.'

5-nitroimidazole : A C-nitro compound that is imidazole bearing a nitro substituent at position 5. [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 CID18208
CHEMBL ID135599
CHEBI ID64635
SCHEMBL ID44903
MeSH IDM0149202

Synonyms (66)

Synonym
AC-1213
4-nitroimidazole
nsc50359
imidazole, 4-nitro-
5-nitroimidazole
3034-38-6
4(5)-nitroimidazole
1h-imidazole, 4-nitro-
nsc-50359
ai3-60154
nsc 50359
einecs 221-224-7
AB-323/25048517
5-nitro-1h-imidazole
MLS001304931
smr000420248
4-nitro-1h-imidazole
inchi=1/c3h3n3o2/c7-6(8)3-1-4-2-5-3/h1-2h,(h,4,5
4-nitroimidazole, 97%
chebi:64635 ,
CHEMBL135599
STK793006
AKOS000561522
N0506
AKOS003613147
A5584
4-nitro-1h-imidazole;5-nitro-1h-imidazole
NCGC00247072-01
1h-imidazole, 5-nitro-
y8u32az5o7 ,
ec 221-224-7
unii-y8u32az5o7
4-nitro-3h-imidazole
5(4)-nitroimidazole
HMS2234E17
100214-79-7
cl 205086
FT-0619234
PS-4383
AM20090417
AB00374225-05
HMS3374L01
AB00374225-07
BBL027506
SCHEMBL44903
imidazole, 4(or 5)-nitro-
1h-5-nitroimidazole
nitroimidazole, 4-
4-nitro-imidazole
DTXSID9062803
W-106949
STR08114
1h-4-nitroimidazole
mfcd00005196
F1791-0019
Z235345333
metronidazole ep impurity b
4-nitroimidazole, vetec(tm) reagent grade, 97%
SY001473
CS-W019995
EN300-27185
metronidazole impurtiy b; 5-nitro-1h-imidazole;1h-imidazole, 4-nitro-
BCP32907
E80412
cl 205086 (9ci)
HY-78644

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" trans-[PtCl2(NH3)-(misonidazole)] is more toxic than the cis isomer."( Platinum complexes with one radiosensitizing ligand [PtCl2(NH3) (sensitizer)]: radiosensitization and toxicity studies in vitro.
Adomat, H; Farrell, NP; Skov, KA, 1987
)
0.27

Bioavailability

ExcerptReferenceRelevance
" In mice, after a single equimolar oral administration, the molecules EU 11100 and 11103 were poorly absorbed and poorly excreted in urine."( Susceptibility of Helicobacter pylori and pharmacokinetic properties in mice of new 5-nitroimidazole derivatives devoid of mutagenic activity in the Ames test.
Bellotti, MG; Dubini, F; Riviera, L; Scaltrito, MM, 1993
)
0.29

Dosage Studied

ExcerptRelevanceReference
" Dosing of TCI and TBI to rats resulted within 24-48 hr in neuronal necrosis within the CNS involving the vestibular nucleus, red nucleus, and outer parietal neocortex and ataxia of the hindlimbs."( The relationship between uncoupling of oxidative phosphorylation and neuronal necrosis within the CNS in rats dosed with trihalogenated imidazoles.
Bird, I; Brown, AW; Ray, DE; Verschoyle, RD, 1987
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
[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)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency75.19300.003245.467312,589.2998AID2517
thioredoxin glutathione reductaseSchistosoma mansoniPotency4.46680.100022.9075100.0000AID485364
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
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.
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.
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.
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.
AID1150145Dissociation constant, apparent pKa of the compound1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
2-pyridylimidazoles as inhibitors of xanthine oxidase.
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.
AID194142The 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 technique; No data1986Journal 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.
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.
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.
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.
AID727731Dissociation constant, pKa of the compound at pH 3 to 12 by UV spectroscopy2013ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1
Rapid Determination of Ionization Constants (pK a) by UV Spectroscopy Using 96-Well Microtiter Plates.
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.
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.
AID172617The amount of the unchanged form of compound detected in the urine samples collected at 0-18 hr after the treatment by HPLC technique; No data1986Journal 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.
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.
AID1150143Inhibition of bovine xanthine oxidase at 2 X 10'-5 M1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
2-pyridylimidazoles as inhibitors of xanthine oxidase.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (115)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (11.30)18.7374
1990's19 (16.52)18.2507
2000's20 (17.39)29.6817
2010's47 (40.87)24.3611
2020's16 (13.91)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.75

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 Index30.75 (24.57)
Research Supply Index4.81 (2.92)
Research Growth Index4.89 (4.65)
Search Engine Demand Index38.04 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.67%)5.53%
Reviews9 (7.50%)6.00%
Case Studies3 (2.50%)4.05%
Observational1 (0.83%)0.25%
Other105 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]