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Azole

Azole
Azole structures.svg

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.)

Contents

Compound classes

The azoles include:

  • 1 nitrogen (but it only includes one nitrogen and no other heteroatom)

A "dioxole" is a similar compound with two oxygen atoms in a five membered ring. Dioxolane is a derivative of dioxole.

Uses

Many azoles are used as antifungal drugs, inhibiting the fungal enzyme 14α-demethylase which produces ergosterol (an important component of the fungal plasma membrane).

Antifungals

Triazole-based

Treatment for hyperthyrodism/thyrotoxicosis

Precautions

Some people are allergic to azole(s).[citation needed]

Some azole drugs have adverse side-effects.[2]

Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome.[3]

References

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.

  1. ^ Eicher, T.; Hauptmann, S. (June 2003). The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications (2nd ed.). John Wiley & Sons. ISBN 3527307206. 
  2. ^ Stein GE, Christensen S, Mummaw N (June 1991). "Comparative study of fluconazole and clotrimazole in the treatment of vulvovaginal candidiasis". DICP 25 (6): 582–5. PMID 1877264. http://www.theannals.com/cgi/content/abstract/25/6/582. Retrieved 2009-11-11. 
  3. ^ Kragie L, Turner SD, Patten CJ, Crespi CL, Stresser DM (August 2002). "Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay". Endocr. Res. 28 (3): 129–40. doi:10.1081/ERC-120015045. PMID 12489563. 

External links


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Look at other dictionaries:

  • Azole — Az ole, n. [From {Azote}.] (Org. Chem.) Any of a large class of compounds characterized by a five membered ring which contains an atom of nitrogen and at least one other noncarbon atom (nitrogen, oxygen, sulphur). The prefixes furo , thio, and… …   The Collaborative International Dictionary of English

  • azole — ● azole nom masculin Composé hétérocyclique aromatique qui renferme un groupe NR dans le cycle à la place d un groupe CH≅CH d un arène …   Encyclopédie Universelle

  • Azole —   Plural, heterozyklische Verbindungen, die in einem fünfgliedrigen Ring mindestens ein Stickstoffatom enthalten …   Universal-Lexikon

  • azole — [az′ōl΄, ə zōl′] n. [ AZ(O) + OLE] any of a group of chemical compounds with a 5 membered ring containing one or more nitrogen atoms: the group consists of the diazoles, triazoles, etc …   English World dictionary

  • Azole — Struktur von Pyrrol Azole, umgangssprachlich auch Pyrrole, sind eine Gruppe heterocyclischer chemischer Verbindungen. Es handelt sich um fünfgliedride stickstoffhaltige heteroaromatische deren Stammverbindung das Pyrrol ist. Durch die formale… …   Deutsch Wikipedia

  • Azole — Cet article concerne la famille de composés dérivés de l azole/pyrrole. Pour la molécule, voir Pyrrole. Les azoles ou pyrroles sont une classe de composés organiques à hétérocycle insaturé à cinq atomes, possédant un atome d azote et quatre… …   Wikipédia en Français

  • azole — SYN: pyrrole. * * * azole ā .zōl, az .ōl n any of numerous compounds characterized by a 5 membered ring containing at least one atom of nitrogen * * * az·ole (azґōl) 1. any of a group of organic compounds containing a five membered… …   Medical dictionary

  • azole — azolas statusas T sritis chemija apibrėžtis Penkianaris heteroaromatinis junginys, turintis žiede du heteroatomus, iš kurių nors vienas yra azotas. atitikmenys: angl. azole rus. азол …   Chemijos terminų aiškinamasis žodynas

  • azole — ˈaˌzōl, ˈā noun ( s) Etymology: International Scientific Vocabulary az + ole 1. : any of a large class of organic compounds that is characterized by a 5 membered ring containing two or more hetero atoms at least one of which is nitrogen and that… …   Useful english dictionary

  • azole antifungal — any of a group of antifungals characterized by the presence of an azole ring structure, which includes the triazoles and the imidazoles (qq.v.). They are usually fungistatic but can be fungicidal at higher concentrations, and act by interfering… …   Medical dictionary

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