An azole is a class of five-membered nitrogen heterocyclic ring compounds containing at least one other non-carbon atom of either nitrogen, sulfur, or oxygen.[1] The parent compounds are aromatic and have two double bonds; there are successively reduced analogs (azolines and azolidines) with fewer. One, and only one, lone pair of electrons from each heteroatom in the ring is part of the aromatic bonding in an azole. Names of azoles maintain the prefix upon reduction (e.g., pyrazoline, pyrazolidine). The numbering of ring atoms in azoles starts with the heteroatom that is not part of a double bond, and then proceeds towards the other heteroatom.
(Six-membered aromatic heterocyclic systems with two nitrogens include pyrimidine and purine, important biochemicals.)
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The azoles include:
A "dioxole" is a similar compound with two oxygen atoms in a five membered ring. Dioxolane is a derivative of dioxole.
Many azoles are used as antifungal drugs, inhibiting the fungal enzyme 14α-demethylase which produces ergosterol (an important component of the fungal plasma membrane).
Some people are allergic to azole(s).
Some azole drugs have adverse side-effects.[2]
Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome.[3]
This article incorporates material from the Citizendium article "Azole", which is licensed under the Creative Commons Attribution-ShareAlike 3.0 Unported License but not under the GFDL.