Nitroimidazole

5-Nitroimidazole^[1]

Names
Preferred IUPAC name 5-Nitro-1H-imidazole
Identifiers
CAS Number	3034-38-6 Y
3D model ( JSmol )	Interactive image
ChemSpider	10637918 Y
ECHA InfoCard	100.019.296
EC Number	221-224-7
PubChem CID	18208
UNII	Y8U32AZ5O7 Y
CompTox Dashboard (EPA)	DTXSID9062803
InChI InChI=1S/C3H3N3O2/c7-6(8)5-2-1-4-3-5/h1-3H Y Key: KUNMIWQQOPACSS-UHFFFAOYSA-N Y
SMILES c1cn(cn1)[N+](=O)[O-]
Properties
Chemical formula	C3H3N3O2
Molar mass	113.076 g·mol−1
Melting point	303 °C (577 °F; 576 K) (decomposes)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	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 their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Nitroimidazoles are the group of

Synthesis

Imidazole undergoes a nitration reaction with a mixture of nitric acid and sulfuric acid to give 5-nitroimidazole.

Nitroimidazole antibiotics

From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitro functional 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 include metronidazole, tinidazole, nimorazole, dimetridazole, pretomanid, ornidazole, megazol, and azanidazole. Drugs based on 2-nitroimidazoles include benznidazole and azomycin.^[3]

Nitroimidazole antibiotics have been used to combat

References