Imidazole
Imidazole
Imidazole (pronounced /ɪˈmɪdəzoʊl/) is an organic compound with the formula C3H4N2. This aromatic heterocyclic is a diazole and one of the fundamental units of the vast class of histidine and histamine.
Etymology
The term "imidazole" was coined by combining the prefix "imide" and the suffix "azole", which are common to a class of organic compounds containing nitrogen.
Structure and properties
Imidazole is a planar five-membered ring. It exists in two equivalent tautomeric forms, because the positive charge can be located on either of the two nitrogen atoms. Imidazole is a highly polar compound, as evidenced by its electric dipole moment of 3.67 D. It is highly soluble in water. Some resonance structures of imidazole are shown below:
N N / \ / \ H C = C H | | N H
Biological significance and applications
Imidazole is part of the structure of several important biomolecules. For instance, it is present in histidine, an amino acid, and hence in many proteins. It is also part of the structure of histamine, a substance released during allergic reactions.
In medicine, imidazole is part of many drugs and has many uses. For example, many antifungal drugs, such as clotrimazole and miconazole, contain an imidazole ring. These drugs work by inhibiting the synthesis of ergosterol, a component of fungal cell membranes.
Related terms
External links
- Medical encyclopedia article on Imidazole
- Wikipedia's article - Imidazole
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