Compounds > 1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole
Page last updated: 2024-11-07

1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole

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Description

1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole: human urinary metabolite of metronidazole; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID121858
CHEMBL ID3544702
CHEBI ID166538
SCHEMBL ID10920908
MeSH IDM0075204

Synonyms (45)

Synonym
2-[2-(hydroxymethyl)-5-nitroimidazol-1-yl]ethanol
4812-40-2
CHEBI:166538
1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole
imidazole-1-ethanol, 2-hydroxymethyl-5-nitro-
ccris 2148
brn 0883934
2-(hydroxymethyl)-5-nitro-1h-imidazole-1-ethanol
metronidazole-oh
FT-0669859
FT-0669858
AKOS006283474
unii-7rui9488il
7rui9488il ,
20396 rp
5-23-10-00558 (beilstein handbook reference)
rp 20396
2-hydroxymetronidazole
rp-20396
2-hydroxymethylmetronidazole
hydroxy metronidazole
1-(2-hydroxyethyl)-2-(hydroxymethyl)-5-nitroimidazole
hydroxymetronidazole
SCHEMBL10920908
1-(.beta.-hydroxyethyl) 2-hydroxymethyl-5-nitroimidazole
imidazole-1-ethanol, 2-(hydroxymethyl)-5-nitro-
1h-imidazole-1-ethanol, 2-(hydroxymethyl)-5-nitro-
hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole, 1-(2-
AEHPOYAOLCAMIU-UHFFFAOYSA-N
CHEMBL3544702
DTXSID20197426
metronidazole-oh, vetranal(tm), analytical standard
1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole; hydroxymetronidazole; 2-(hydroxymethyl)-5-nitroimidazole-1-ethanol
metronidazole-hydroxy
1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole (hydroxymetronidazole)
Q5955628
2-(2-(hydroxymethyl)-5-nitro-1h-imidazol-1-yl)ethanol
2-[2-(hydroxymethyl)-5-nitro-1h-imidazol-1-yl]ethan-1-ol
metronidazole-hydroxy 100 microg/ml in acetonitrile
2-[2-(hydroxymethyl)-5-nitro-imidazol-1-yl]ethanol
metronidazole-hydroxy 100 microg/ml in methanol
CS-0129416
AS-82869
HY-136440
AKOS040758158

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic indices were found to be independent of the dose administered."( Steady-state pharmacokinetics of metronidazole in Crohn's disease.
Eradiri, O; Jamali, F; Thomson, AB, )		0.13
" Pharmacokinetic parameters for metronidazole and hydroxymetronidazole were calculated, and the significance of the mean differences in parameters between omeprazole and placebo co-administration was assessed using a two-tailed, paired t-test."( The effect of omeprazole on the pharmacokinetics of metronidazole and hydroxymetronidazole in human plasma, saliva and gastric juice.
Barrett, DA; Goddard, AF; Jessa, MJ; Shaw, PN; Spiller, RC, 1997)		0.3
"05) in any of the plasma or saliva pharmacokinetic parameter values for metronidazole between volunteers receiving omeprazole or placebo when metronidazole was administered either as an intravenous infusion or orally."( The effect of omeprazole on the pharmacokinetics of metronidazole and hydroxymetronidazole in human plasma, saliva and gastric juice.
Barrett, DA; Goddard, AF; Jessa, MJ; Shaw, PN; Spiller, RC, 1997)		0.3
" The method was successfully applied to determine metronidazole and 2-hydroxymetronidazole plasma concentrations in a pharmacokinetic study conducted in adults administered an oral dose of 500 mg metronidazole."( Development of a UPLC-MS/MS method for quantitation of metronidazole and 2-hydroxy metronidazole in human plasma and its application to a pharmacokinetic study.
Abdel-Rahman, S; Pearce, RE; Stancil, SL; van Haandel, L, 2018)		0.48

Bioavailability

ExcerptReferenceRelevance
" Bioavailability of the drug was 19 +/- 3% after the vaginal dose as compared to 100 +/- 5% after the oral dose."( Systemic concentrations of metronidazole and its main metabolites after intravenous oral and vaginal administration.
Fredricsson, B; Hagström, B; Nord, CE; Rane, A, 1987)		0.27
" The bioavailability of oral doses of metronidazole is 88-95%, that of tinidazole 90%."( Antibacterial activity and pharmacokinetics of nitroimidazoles. A review.
Bergan, T, 1985)		0.27

Dosage Studied

ExcerptRelevanceReference
" This would suggest that cumulative penetration of metronidazole from the systemic circulation into the peritoneal cavity with dosing every 8 h should lead to adequate concentrations for the treatment of anaerobic peritonitis."( Pharmacokinetics of metronidazole in patients undergoing continuous ambulatory peritoneal dialysis.
Baxter, H; Guay, DR; Jacyk, WR; Meatherall, RC; Penner, B, 1984)		0.27
" No side effects of metronidazole were noted and its extended half life in neonates suggests that less frequent dosage would be appropriate."( Intravenous metronidazole in the newborn.
Hall, P; Kaye, CM; McIntosh, N; Steele, J, 1983)		0.27
" Pharmacokinetic studies of metronidazole and its hydroxy metabolite have shown that the MICs of both compounds remain above the MICs for most anaerobic organisms over an 8-h dosing interval."( In vitro activities of metronidazole and its hydroxy metabolite against Bacteroides spp.
Danziger, LH; Pendland, SL; Piscitelli, SC; Schreckenberger, PC, 1994)		0.29
"To evaluate the effect of omeprazole on the pharmacokinetics of metronidazole and hydroxymetronidazole in plasma, gastric juice and saliva following intravenous infusion or oral dosing of metronidazole."( The effect of omeprazole on the pharmacokinetics of metronidazole and hydroxymetronidazole in human plasma, saliva and gastric juice.
Barrett, DA; Goddard, AF; Jessa, MJ; Shaw, PN; Spiller, RC, 1997)		0.3
[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]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (59.26)18.7374
1990's7 (25.93)18.2507
2000's0 (0.00)29.6817
2010's3 (11.11)24.3611
2020's1 (3.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.88

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

MetricThis Compound (vs All)
Research Demand Index10.88 (24.57)
Research Supply Index3.47 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.88)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (6.90%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other27 (93.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
metronidazole
Metronidazole: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.. metronidazole : A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.		6.56272C-nitro compound;
imidazoles;
primary alcohol		antiamoebic agent;
antibacterial drug;
antimicrobial agent;
antiparasitic agent;
antitrichomonal drug;
environmental contaminant;
prodrug;
radiosensitizing agent;
xenobiotic
omeprazole
Omeprazole: A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.. omeprazole : A racemate comprising equimolar amounts of (R)- and (S)-omeprazole.. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole : A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.		3.3811aromatic ether;
benzimidazoles;
pyridines;
sulfoxide
tinidazole
Tinidazole: A nitroimidazole alkylating agent that is used as an antitrichomonal agent against TRICHOMONAS VAGINALIS; ENTAMOEBA HISTOLYTICA; and GIARDIA LAMBLIA infections. It also acts as an antibacterial agent for the treatment of BACTERIAL VAGINOSIS and anaerobic bacterial infections.. tinidazole : 1H-imidazole substituted at C-1 by a (2-ethylsulfonyl)ethyl group, at C-2 by a methyl group and at C-5 by a nitro group. It is used as an antiprotozoal, antibacterial agent.		2.8840imidazolesantiamoebic agent;
antibacterial drug;
antiparasitic agent;
antiprotozoal drug
azomycin
azomycin: RN given refers to parent cpd with specified locant; structure		1.9610C-nitro compound;
imidazoles		antitubercular agent
amoxicillin
Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.		1.9710penicillin allergen;
penicillin		antibacterial drug
2-methyl-5-nitroimidazol-1-ylacetic acid
2-methyl-5-nitroimidazol-1-ylacetic acid: human urinary metabolite of metronidazole; structure		2.8840organonitrogen compound;
organooxygen compound
azlocillin
Azlocillin: A semisynthetic ampicillin-derived acylureido penicillin.. azlocillin : A semisynthetic penicillin having a 6beta-{(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl}amino side-group. It is an antibiotic used in treating infections caused by Pseudomonas aeruginosa, Escherichia coli and Haemophilus influenzae.		1.9610penicillin allergen;
penicillin;
semisynthetic derivative		antibacterial drug
ConditionIndicatedRelationship StrengthStudiesTrials
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.1310
Colitis, Granulomatous
[description not available]		01.9610
Crohn Disease
A chronic transmural inflammation that may involve any part of the DIGESTIVE TRACT from MOUTH to ANUS, mostly found in the ILEUM, the CECUM, and the COLON. In Crohn disease, the inflammation, extending through the intestinal wall from the MUCOSA to the serosa, is characteristically asymmetric and segmental. Epithelioid GRANULOMAS may be seen in some patients.		01.9610
Haemophilus Infections
Infections with bacteria of the genus HAEMOPHILUS.		01.9610
Vaginitis
Inflammation of the vagina characterized by pain and a purulent discharge.		01.9610
Bacterial Disease
[description not available]		01.9610
Infant, Newborn, Diseases
Diseases of newborn infants present at birth (congenital) or developing within the first month of birth. It does not include hereditary diseases not manifesting at birth or within the first 30 days of life nor does it include inborn errors of metabolism. Both HEREDITARY DISEASES and METABOLISM, INBORN ERRORS are available as general concepts.		01.9610
Bacterial Infections
Infections by bacteria, general or unspecified.		01.9610
Cirrhosis, Liver
[description not available]		03.3711
Schistosoma mansoni Infection
[description not available]		03.3711
Liver Cirrhosis
Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.		03.3711
Schistosomiasis mansoni
Schistosomiasis caused by Schistosoma mansoni. It is endemic in Africa, the Middle East, South America, and the Caribbean and affects mainly the bowel, spleen, and liver.		03.3711
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		01.9910
Alcoholic Cirrhosis
[description not available]		0210
Liver Dysfunction
[description not available]		0210
Alcohol Drinking
Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.		0210
Liver Cirrhosis, Alcoholic
FIBROSIS of the hepatic parenchyma due to chronic excess ALCOHOL DRINKING.		0210
Liver Diseases
Pathological processes of the LIVER.		0210
Abnormalities, Autosome
[description not available]		01.9510
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		01.9710
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9710
Pericementitis
[description not available]		01.9710
Periodontitis
Inflammation and loss of connective tissues supporting or surrounding the teeth. This may involve any part of the PERIODONTIUM. Periodontitis is currently classified by disease progression (CHRONIC PERIODONTITIS; AGGRESSIVE PERIODONTITIS) instead of age of onset. (From 1999 International Workshop for a Classification of Periodontal Diseases and Conditions, American Academy of Periodontology)		01.9710
Antibiotic-Associated Colitis
[description not available]		01.9610
Enterocolitis, Pseudomembranous
An acute inflammation of the INTESTINAL MUCOSA that is characterized by the presence of pseudomembranes or plaques in the SMALL INTESTINE (pseudomembranous enteritis) and the LARGE INTESTINE (pseudomembranous colitis). It is commonly associated with antibiotic therapy and CLOSTRIDIUM DIFFICILE colonization.		01.9610