 | |
| Names | |
|---|---|
| Preferred IUPAC name 5-Nitro-1H-imidazole | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider |
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| ECHA InfoCard | 100.019.296 |
| EC Number |
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| UNII | |
| |
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| Properties | |
| C3H3N3O2 | |
| Molar mass | 113.076 g·mol−1 |
| Melting point | 303 °C (577 °F; 576 K) (decomposes) |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H302 | |
| P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P312,P304+P340,P305+P351+P338,P312,P321,P322,P330,P332+P313,P337+P313,P362,P363,P403+P233,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Nitroimidazoles are the group oforganic compounds consisting of animidazole ring with at least onenitro group substituent. The term also refers to the class of antibiotics that have nitroimidazole in their structures.[2] These antibiotics commonly include the 5-nitroimidazolepositional isomer.
Imidazole undergoes anitration reaction with a mixture ofnitric acid andsulfuric acid to give 5-nitroimidazole.
From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitrofunctional group. Structures with names 4- and 5-nitroimidazole are equivalent from the perspective of drugs since these tautomers readily interconvert. Drugs of the 5-nitro variety includemetronidazole,tinidazole,nimorazole,dimetridazole,pretomanid,ornidazole,megazol, andazanidazole. Drugs based on 2-nitroimidazoles includebenznidazole andazomycin.[3]
Nitroimidazole antibiotics have been used to combatanaerobicbacterial andparasiticinfections.[4] Perhaps the most common example ismetronidazole. Other heterocycles such as nitrothiazoles (thiazole) are also used for this purpose. Nitroheterocycles may bereductively activated inhypoxic cells, and then undergoredox recycling ordecompose to toxic products.[5]
