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Imidazoles

Drugs and Chemicals · NLM MeSH · updated 2026-10-31 · version 1

Citations verified against PubMedNot yet clinician-reviewed9 referencesApproximately 3 min read

Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons.

Table of Contents

1. Definition2. Research landscape3. Reading the evidence4. Open-access studies5. Key reviews6. References7. About this article

Definition and research guide

This page combines a MeSH definition, publication statistics and selected research abstracts. It is a starting point for reading the literature, not a medical textbook or a systematic evidence review.

Content available: 3 complete abstracts (651 words), 9 references. Full article text is not stored or reproduced here; follow the PMID, DOI or PMC links to read the original sources and their access terms.

Definition

Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include imidazolines and imidazolidines. Distinguish from 1,2-diazole (pyrazoles).

Definition: NLM Medical Subject Headings (MeSH) scope note (Public domain (U.S. National Library of Medicine); attribution requested). View the MeSH record.

Where it fits in the MeSH classification

Broader topics
Azoles
Narrower topics
4-(3-Butoxy-4-methoxybenzyl)-2-imidazolidinone; Aminoimidazole Carboxamide; Antazoline; Biotin; Bis(4-Methyl-1-Homopiperazinylthiocarbonyl)disulfide; Carbimazole; Cimetidine; Clotrimazole; Creatinine; Dacarbazine; Dexmedetomidine; Econazole; Enoximone; Etimizol
See also
Benzimidazoles

Related concepts

  • Imidazolines
  • Imidazolidines
  • Pyrazoles

Research landscape

PubMed indexes 302,982 records tagged with the MeSH heading “Imidazoles” (counts retrieved 2026-10-31). 37,685 of them (12.4%) were published from 2020 onward, and the busiest period so far is through 1999 with 143,542 records.

Reviews account for 17,556 records (5.8%) and meta-analyses for 2,010. Randomized controlled trials number 18,177 (6.0%) as a share of all records on the topic.

PubMed records by publication periodthrough 1999: 143,542 records; 2000-2009: 54,421 records; 2010-2019: 67,334 records; 2020 onward: 37,685 records143,542through 199954,4212000-200967,3342010-201937,6852020 onward
Records in PubMed indexed with this heading, by publication period. Real counts from NCBI E-utilities; the final period covers only part of the current year. Volume reflects how much has been published, not how strong the evidence is.
Show the data
PeriodRecords
through 1999143,542
2000-200954,421
2010-201967,334
2020 onward37,685
Share of records by publication typeReviews: 5.8 percent; Meta-analyses: 0.7 percent; Randomized controlled trials: 6.0 percentReviews5.8% (17,556)Meta-analyses0.7% (2,010)Randomized controlled trials6.0% (18,177)
Share of all PubMed records on this heading that carry each publication type. Types overlap with other records, so the shares do not sum to 100%.
Publication-type chart data
Publication types among 302,982 PubMed records
TypeRecordsShare
Reviews17,5565.8%
Meta-analyses2,0100.7%
Randomized controlled trials18,1776.0%

Method: PubMed query "Imidazoles"[MeSH Terms] with publication-type and date filters, retrieved 2026-10-31.

Reading the evidence in drugs and chemicals

Studies of a chemical or drug can answer very different questions: what it is and how it behaves in cells and animals, how the body handles it, and whether it changes outcomes in people. Laboratory and animal findings often do not carry over to patients, and observational studies of exposures are confounded by who uses a substance and why. Nothing on this page is a recommendation to use, avoid, start or stop any substance or medicine; talk to a qualified clinician or pharmacist about your own situation. Check the dose, the species, the comparison group and whether a patient-relevant outcome was measured.

Evidence from open-access studies

These open-access studies come from PubMed’s best-match results for this heading (papers whose main topic it is), ranked here by citation count, with one recent addition. Each abstract is reproduced in full under its recorded open licence so that you can read the authors’ own words. They illustrate the literature; they are not a systematic summary of it. Citation counts measure attention, not reliability or clinical benefit.

Study comparison — selected abstracts, not a systematic review
Study / authorsYearSource label / designEurope PMC citationsLicence / source
Gut bacterial metabolite imidazole propionate potentiates Alzheimer's disease pathology
Vemuganti V, Kang JW, Zhang Q, McGregor ER, Hilser JR, Aquino-Martinez R, et al.
2026Research article
Design not recorded in structured metadata
4cc by
PMID 42362546 · DOI · PMC13454616
Histaminylation alters collagen matrix mechanics and attenuates cardiac fibrosis post-myocardial infarction via mechanotransduction signaling axis
Zhu J, Sun D, Zeng G, Wu K, Yang X, Zhu X, et al.
2026Research article
Design not recorded in structured metadata
2cc by
PMID 42270610 · DOI · PMC13254370
Evaluating the Impact of Clonidine and Midazolam Premedication on Emergence Delirium in Pediatric Patients
Garioud ALB, Taplin A, Shang Y, Khan RN, Sommerfield D, Hauser N, et al.
2026Research article
Design not recorded in structured metadata
1cc by
PMID 42538855 · DOI · PMC13551259

Gut bacterial metabolite imidazole propionate potentiates Alzheimer's disease pathology [1]

Research article Vemuganti V, Kang JW, Zhang Q, McGregor ER, Hilser JR, Aquino-Martinez R, et al. · · 2026 · cited 4 times (Europe PMC)

Abstract reading summary — source excerpts
Opening excerpt
The gut microbiome modulates metabolic and neurovascular processes implicated in Alzheimer's disease and related dementias (ADRD), but the underlying mechanisms remain unclear.
Closing excerpt
Together, this study links ImP to hallmarks of neurodegeneration and suggests that targeting ImP may represent a potential strategy to modify ADRD risk.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (162 words)

The gut microbiome modulates metabolic and neurovascular processes implicated in Alzheimer's disease and related dementias (ADRD), but the underlying mechanisms remain unclear. Here, we identify the bacterial metabolite imidazole propionate (ImP) as a modifier of ADRD pathology. In a cohort of 1196 cognitively unimpaired adults, higher plasma ImP levels were associated with lower preclinical cognitive scores and biomarkers of ADRD, both cross-sectionally and longitudinally. Fecal metagenomic analysis linked putative ImP producers to ADRD phenotypes. Genome-wide integrative analysis revealed a locus on chromosome 12 associated with both plasma ImP levels and AD risk in humans, supporting a host genetic contribution to ImP regulation and a causal role of this metabolite in AD. In mice, chronic ImP administration exacerbated AD-like pathology. ImP impaired brain endothelial barrier and promoted tau hyperphosphorylation in primary neurons, an effect blocked by glycogen synthase kinase-3β inhibition. Together, this study links ImP to hallmarks of neurodegeneration and suggests that targeting ImP may represent a potential strategy to modify ADRD risk.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 42362546 · DOI · PMC13454616

Histaminylation alters collagen matrix mechanics and attenuates cardiac fibrosis post-myocardial infarction via mechanotransduction signaling axis [2]

Research article Zhu J, Sun D, Zeng G, Wu K, Yang X, Zhu X, et al. · · 2026 · cited 2 times (Europe PMC)

Abstract reading summary — source excerpts
Opening excerpt
Histaminylation is a newly discovered monoaminylation catalyzed by transglutaminase 2 (TGM2), and its role in myocardial fibrosis has not yet been elucidated.
Closing excerpt
This study also highlights a novel role of histamine in maintaining stress environment mechanical stability.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (245 words)

Histaminylation is a newly discovered monoaminylation catalyzed by transglutaminase 2 (TGM2), and its role in myocardial fibrosis has not yet been elucidated. Here, we identified histaminylation in cardiac type I collagen isolated from mice 7 days after acute myocardial infarction (AMI) by mass spectrometry. Using histamine-deficient Hdc-/- mice, we demonstrated an increase in TGM2-mediated γ-glutamyl-ε-lysine crosslinks and a higher myocardial Young's modulus in the scar region of Hdc-/- mice than in wild-type controls, indicating that histaminylation might restrain the role of TGM2 in cardiac fibrogenesis after AMI. Furthermore, we reconstituted an in vitro crosslinking system, yielding unmodified collagen and histaminylated collagen. The results of mechanical indentation and electron microscopy demonstrated that histaminylation could reduce crosslink formation, lower matrix stiffness, and alter viscoelasticity. Subsequently, primary murine cardiac fibroblasts were cultured under cyclic stretch with TGF-β on different substrates, and the results revealed that histaminylated collagen strongly attenuated TGF-β-induced fibroblast-to-myofibroblast transition and reduced focal adhesion assembly. Mechanically, integrated single-cell and bulk RNA-seq analyses indicated that the PIEZO1/ITGB1 mechanotransduction axis was upregulated and mediated downstream signal transduction in the infarcted hearts of Hdc-/- mice. Finally, local delivery of a histamine-releasing hydrogel to Hdc-/- mice after AMI could significantly reinstate collagen histaminylation and reduce crosslink abundance and cardiac dysfunction. Collectively, these data reveal that collagen histaminylation limits TGM2-dependent crosslinking, softens the extracellular matrix, and inhibits the PIEZO1/ITGB1 axis, thereby mitigating myocardial fibrosis after AMI. This study also highlights a novel role of histamine in maintaining stress environment mechanical stability.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 42270610 · DOI · PMC13254370

Evaluating the Impact of Clonidine and Midazolam Premedication on Emergence Delirium in Pediatric Patients [3]

Research article Garioud ALB, Taplin A, Shang Y, Khan RN, Sommerfield D, Hauser N, et al. · · 2026 · cited 1 times (Europe PMC)

Abstract reading summary — source excerpts
Opening excerpt
BackgroundPreoperative anxiety is common in children and is associated with emergence delirium-a distressing postoperative complication characterized by agitation and disorientation.
Closing excerpt
While clonidine showed no statistically significant association with emergence delirium, our secondary multivariate analysis suggests midazolam might be associated with an increased risk of emergence delirium.
Interpretation limits
Verbatim excerpts from the authors’ abstract; the closing excerpt may describe a finding, limitation or recommendation. Design, population, effect size and uncertainty have not been independently extracted or appraised. Read the complete abstract and linked paper before interpreting the findings.
Read complete abstract (244 words)

BackgroundPreoperative anxiety is common in children and is associated with emergence delirium-a distressing postoperative complication characterized by agitation and disorientation. Midazolam has long been the drug of choice for preoperative anxiolysis. More recently, α2 adrenoceptor agonists, such as clonidine, have gained popularity for their sedative and analgesic properties. The effect of these agents on the incidence of emergence delirium remains uncertain. This study evaluated whether premedication with clonidine or midazolam is associated with emergence delirium in children undergoing general anesthesia.MethodsWe performed a post hoc analysis of prospectively collected data pooled from 10 clinical studies, comprising data from 4796 general anesthetics in children (0-16 years). The studies were carried out at a tertiary pediatric hospital in Perth, Australia. We assessed the impact of premedication with clonidine or midazolam on the incidence of emergence delirium using validated scales.ResultsIn this cohort, with a mean age of 6.8 (range: 0.03-16.97), 331 children received clonidine and 731 received midazolam. Overall, the incidence of emergence delirium was 6%. Primary propensity score-matched analyses found no significant association between clonidine (OR 1.19, 95% CI 0.65-2.16) or midazolam (OR 1.23, 95% CI 0.79-1.92) and emergence delirium. In our secondary adjusted logistic regression models, midazolam was associated with increased odds of emergence delirium, whereas clonidine showed no statistically significant association overall.ConclusionsThe overall incidence of emergence delirium was low. While clonidine showed no statistically significant association with emergence delirium, our secondary multivariate analysis suggests midazolam might be associated with an increased risk of emergence delirium.

Abstract reproduced from the open-access article under the recorded cc by licence; © the authors. PMID 42538855 · DOI · PMC13551259

Key reviews and meta-analyses

The most cited review-type papers among PubMed’s best-match results for this heading, listed with bibliographic details only. Follow the links for the full text and access terms.

  • Research article Comparative efficacy and tolerability of medications for attention-deficit hyperactivity disorder in children, adolescents, and adults: a systematic review and network meta-analysis [4]
    Cortese S, Adamo N, Del Giovane C, Mohr-Jensen C, Hayes AJ, Carucci S, et al. · Lancet Psychiatry · 2018 · cited 929 times (Europe PMC)
  • Research article Estimated Glomerular Filtration Rate, Albuminuria, and Adverse Outcomes: An Individual-Participant Data Meta-Analysis [5]
    Writing Group for the CKD Prognosis Consortium, Grams ME, Coresh J, Matsushita K, Ballew SH, Sang Y, et al. · JAMA · 2023 · cited 339 times (Europe PMC)
  • Research article Conversion of Urine Protein-Creatinine Ratio or Urine Dipstick Protein to Urine Albumin-Creatinine Ratio for Use in Chronic Kidney Disease Screening and Prognosis : An Individual Participant-Based Meta-analysis [6]
    Sumida K, Nadkarni GN, Grams ME, Sang Y, Ballew SH, Coresh J, et al. · Ann Intern Med · 2020 · cited 302 times (Europe PMC)
  • Research article Intra-operative analgesia with remifentanil vs. dexmedetomidine: a systematic review and meta-analysis with trial sequential analysis [7]
    Grape S, Kirkham KR, Frauenknecht J, Albrecht E · Anaesthesia · 2019 · cited 154 times (Europe PMC)
  • Research article Albuminuria Testing in Hypertension and Diabetes: An Individual-Participant Data Meta-Analysis in a Global Consortium [8]
    Shin JI, Chang AR, Grams ME, Coresh J, Ballew SH, Surapaneni A, et al. · Hypertension · 2021 · cited 138 times (Europe PMC)
  • Research article Dexmedetomidine vs other sedatives in critically ill mechanically ventilated adults: a systematic review and meta-analysis of randomized trials [9]
    Lewis K, Alshamsi F, Carayannopoulos KL, Granholm A, Piticaru J, Al Duhailib Z, et al. · Intensive Care Med · 2022 · cited 133 times (Europe PMC)

References

  1. Vemuganti V, Kang JW, Zhang Q, McGregor ER, Hilser JR, Aquino-Martinez R, et al.. Gut bacterial metabolite imidazole propionate potentiates Alzheimer's disease pathology. . 2026. PMID 42362546 · DOI · PMC13454616
  2. Zhu J, Sun D, Zeng G, Wu K, Yang X, Zhu X, et al.. Histaminylation alters collagen matrix mechanics and attenuates cardiac fibrosis post-myocardial infarction via mechanotransduction signaling axis. . 2026. PMID 42270610 · DOI · PMC13254370
  3. Garioud ALB, Taplin A, Shang Y, Khan RN, Sommerfield D, Hauser N, et al.. Evaluating the Impact of Clonidine and Midazolam Premedication on Emergence Delirium in Pediatric Patients. . 2026. PMID 42538855 · DOI · PMC13551259
  4. Cortese S, Adamo N, Del Giovane C, Mohr-Jensen C, Hayes AJ, Carucci S, et al.. Comparative efficacy and tolerability of medications for attention-deficit hyperactivity disorder in children, adolescents, and adults: a systematic review and network meta-analysis. Lancet Psychiatry. 2018. PMID 30097390 · DOI · PMC6109107
  5. Writing Group for the CKD Prognosis Consortium, Grams ME, Coresh J, Matsushita K, Ballew SH, Sang Y, et al.. Estimated Glomerular Filtration Rate, Albuminuria, and Adverse Outcomes: An Individual-Participant Data Meta-Analysis. JAMA. 2023. PMID 37787795 · DOI · PMC10548311
  6. Sumida K, Nadkarni GN, Grams ME, Sang Y, Ballew SH, Coresh J, et al.. Conversion of Urine Protein-Creatinine Ratio or Urine Dipstick Protein to Urine Albumin-Creatinine Ratio for Use in Chronic Kidney Disease Screening and Prognosis : An Individual Participant-Based Meta-analysis. Ann Intern Med. 2020. PMID 32658569 · DOI · PMC7780415
  7. Grape S, Kirkham KR, Frauenknecht J, Albrecht E. Intra-operative analgesia with remifentanil vs. dexmedetomidine: a systematic review and meta-analysis with trial sequential analysis. Anaesthesia. 2019. PMID 30950522 · DOI
  8. Shin JI, Chang AR, Grams ME, Coresh J, Ballew SH, Surapaneni A, et al.. Albuminuria Testing in Hypertension and Diabetes: An Individual-Participant Data Meta-Analysis in a Global Consortium. Hypertension. 2021. PMID 34365812 · DOI · PMC8429211
  9. Lewis K, Alshamsi F, Carayannopoulos KL, Granholm A, Piticaru J, Al Duhailib Z, et al.. Dexmedetomidine vs other sedatives in critically ill mechanically ventilated adults: a systematic review and meta-analysis of randomized trials. Intensive Care Med. 2022. PMID 35648198 · DOI

About this article

Sources
NLM Medical Subject Headings (definition, synonyms); NCBI PubMed (counts, identifiers); Europe PMC (open-access abstracts and citation counts).
Verification
Every reference was resolved against PubMed on 2026-10-31; title, year and DOI matched.
Review state
automated source verified; no human expert review has been recorded yet.
Version
1, last updated 2026-10-31.

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All 546 articles in Drugs and Chemicals →

At a glance

302,982
PubMed records on this heading
12%
published since 2020
17,556
review articles
18,177
randomized trials
9
verified references below

Counts come from PubMed on 2026-10-31; they show how much has been written, not how strong the evidence is.

Related topics See all →

  • AcetazolamideDrugs and Chemicals
  • AminopyrineDrugs and Chemicals
  • AnastrozoleDrugs and Chemicals
  • AntipyrineDrugs and Chemicals
  • AtorvastatinDrugs and Chemicals

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