Imidazole – Uses, Dosage, Side Effects, Interactions

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Imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colorless solid that...

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Article Summary

Imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colorless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution....

Key Takeaways

  • This article explains Mechanism: in simple medical language.
  • This article explains Indications: in simple medical language.
  • This article explains Contraindications: in simple medical language.
  • This article explains Dosages: in simple medical language.
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Definition

Imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole.

Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colorless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.

Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.

Mechanism:

Imidazole has a unique structure that allows it to function as a heterocyclic aromatic compound. It is involved in various biological and pharmacological processes due to its ability to coordinate with metal ions and participate in electron transfer reactions. Imidazole also acts as a buffer in biochemical and chemical reactions, maintaining a stable pH. It can form coordination complexes with metal ions, making it important in metalloenzymes and metalloproteins.

Indications:

  1. Antifungal Agent: Imidazole derivatives, such as ketoconazole and miconazole, are used to treat fungal infections.
  2. Vasodilator: Imidazole can be used in some formulations to dilate blood vessels, aiding in conditions like Raynaud’s disease.
  3. Buffer Agent: Imidazole acts as a buffer in biochemical and chemical reactions.
  4. Chelating Agent: It can be used to chelate metal ions in analytical chemistry.
  5. Antiparasitic Agent: Some imidazole compounds are used in the treatment of parasitic infections.
  6. Chemical Synthesis: Imidazole is used as a reagent in various chemical syntheses.
  7. Coordination Chemistry: In coordination chemistry, imidazole is employed in the synthesis of metal complexes.
  8. Stabilizer: Imidazole is used in the formulation of certain pharmaceuticals and cosmetics to stabilize the product.
  9. Antibacterial Agent: Some imidazole derivatives have antibacterial properties.
  10. Research: Imidazole is used in research laboratories for a variety of applications, including protein purification and enzyme assays.

Contraindications:

  1. Hypersensitivity to clotrimazole or any of its components
  2. Use in the eyes
  3. Concurrent use with certain other medications without physician’s advice
  4. History of allergic reaction to other imidazole derivatives
  5. Before any diagnostic procedures of the vaginal area
  6. Children under a certain age without physician’s advice
  7. Bacterial infections (it’s anti-fungal, not antibacterial)
  8. Viral infections (like herpes or chickenpox)
  9. For internal use unless prescribed
  10. Use on open wounds or burns

Dosages:

  • Topical preparations: Generally applied once to three times daily depending on the formulation and severity of the infection.
  • Vaginal preparations: Usually inserted once daily, often at bedtime, for a duration determined by the severity of the infection.

 Side Effects

  1. Redness
  2. Irritation
  3. Burning sensation
  4. Stinging
  5. Swelling
  6. Peeling
  7. Rash
  8. Itching
  9. Urticaria
  10. Blisters
  11. Dryness
  12. Crusting
  13. Numbness
  14. Edema
  15. Vesicles
  16. Pustules
  17. Discomfort
  18. pain when an area is touched or pressed. সহজ বাংলা: চাপ দিলে ব্যথা।" data-rx-term="tenderness" data-rx-definition="Tenderness means pain when an area is touched or pressed. সহজ বাংলা: চাপ দিলে ব্যথা।">Tenderness
  19. Foul-smelling discharge (with vaginal use)
  20. Abdominal cramps (with vaginal use)
  21. Nausea
  22. Contact dermatitis
  23. allergy, infection, or inflammation. সহজ বাংলা: চামড়া লাল হয়ে যাওয়া।" data-rx-term="erythema" data-rx-definition="Erythema means skin redness, often from irritation, allergy, infection, or inflammation. সহজ বাংলা: চামড়া লাল হয়ে যাওয়া।">Erythema
  24. Scaling
  25. Tingling
  26. Maceration
  27. Striae (stretch marks)
  28. Secondary infection
  29. Hyperpigmentation
  30. Hypersensitivity reaction

Drug Interactions

  1. Amphotericin B
  2. Nystatin
  3. Flucytosine
  4. Other antifungal agents
  5. Topical corticosteroids
  6. Topical retinoids
  7. Topical calcineurin inhibitors
  8. Warfarin
  9. Certain antihistamines
  10. Certain antiseizure medications
  11. Certain antibiotics
  12. Antacids
  13. Certain antiarrhythmic medications
  14. Certain antipsychotics
  15. Antidiabetics
  16. Certain antihypertensives
  17. Immunosuppressants
  18. Antiretrovirals
  19. Benzodiazepines
  20. Beta-blockers
  21. Calcium channel blockers
  22. Certain cholesterol-lowering drugs
  23. Oral contraceptives
  24. Digitalis glycosides
  25. Diuretics
  26. Certain gastrointestinal motility drugs
  27. Opioid analgesics
  28. Certain antimalarials
  29. NSAIDs
  30. Thyroid hormones

Pregnancy and Lactation:

  • Pregnancy: Clotrimazole is classified as pregnancy category B, which means there’s no evidence of risk in humans based on studies. However, it’s still crucial to consult a physician before using clotrimazole during pregnancy.
  • Lactation: While clotrimazole is considered safe during breastfeeding, it’s essential to ensure that the infant doesn’t come into direct contact with treated areas

  1. DrugBank
  2. CAS Common Chemistry
  3. ChemIDplus
    ChemIDplus Chemical Information Classification

    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus

  4. DTP/NCI
  5. EPA Chemicals under the TSCA
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists

    https://comptox.epa.gov/dashboard/chemical-lists/

  7. European Chemicals Agency (ECHA)
  8. FDA Global Substance Registration System (GSRS)
  9. Hazardous Substances Data Bank (HSDB)
  10. Human Metabolome Database (HMDB)
  11. ILO-WHO International Chemical Safety Cards (ICSCs)
  12. ChEBI
  13. LOTUS – the natural products occurrence database
  14. ChEMBL
  15. Crystallography Open Database (COD)
  16. EPA Chemical and Products Database (CPDat)
  17. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
  18. EU REGULATION (EC) No 1272/2008
  19. Hazardous Chemical Information System (HCIS), Safe Work Australia
  20. NITE-CMC
  21. MassBank of North America (MoNA)
  22. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.

    https://www.nist.gov/srd/public-law

  23. SpectraBase
  24. Wikipedia
  25. Japan Chemical Substance Dictionary (Nikkaji)
  26. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license

    https://www.kegg.jp/kegg/legal.html

  27. KNApSAcK Species-Metabolite Database
  28. Natural Product Activity and Species Source (NPASS)
  29. MassBank Europe
  30. Metabolomics Workbench
  31. Nature Chemistry
  32. NIPH Clinical Trials Search of Japan
  33. NMRShiftDB
  34. NORMAN Suspect List Exchange
    NORMAN Suspect List Exchange Classification

    https://www.norman-network.com/nds/SLE/

  35. Rhea – Annotated Reactions Database
  36. Springer Nature
  37. SpringerMaterials
  38. The Cambridge Structural Database
  39. Thieme Chemistry
  40. Wikidata
  41. Wiley
  42. PubChem
  43. Medical Subject Headings (MeSH)
  44. UN Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
  45. EPA Substance Registry Services
  46. PATENTSCOPE (WIPO)

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  2. Step 2

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  4. Step 4

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  5. Step 5

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