Nitroimidazole

5-Nitroimidazole

Names
IUPAC name 5-Nitro-1H-imidazole
Identifiers
CAS Number	100214-79-7 N
3D model (Jmol)	Interactive image
ChemSpider	10637918 Y
PubChem	18208
InChI InChI=1S/C3H3N3O2/c7-6(8)5-2-1-4-3-5/h1-3H Y Key: KUNMIWQQOPACSS-UHFFFAOYSA-N Y InChI=1/C3H3N3O2/c7-6(8)5-2-1-4-3-5/h1-3H Key: KUNMIWQQOPACSS-UHFFFAOYAV
SMILES c1cn(cn1)[N+](=O)[O-]
Properties
Chemical formula	C3H3N3O2
Molar mass	113.07 g/mol
Melting point	303 °C (577 °F; 576 K) (decomposes)
Hazards
Main hazards	Xn
R-phrases	R20/21/22 R36/37/38
S-phrases	S26 S36/37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

5-Nitroimidazole is an organic compound with the formula O₂NC₃H₂N₂H. The nitro group at position 5 on the imidazole ring is the most common positional isomer. The term nitroimidazole also refers to a class of antibiotics that share similar chemical structures.

2-Nitroimidazole (azomycin) is used in the synthesis of Etanidazole.

Imidazole reacts with a mixture of nitric acid to give 5-nitroimidazole:

Under conventional conditions for nitration, the reaction is conducted in the presence of sulfuric acid.

From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitro functional group. 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, 6-Amino PA824, ornidazole, megazol, and azanidazole. Drugs based on 2-nitromidazoles include benznidazole.

Nitroimidazole antibiotics have been used to combat anaerobic bacterial and parasitic infections. Perhaps the most common example is metronidazole. Other heterocycles such as nitrothiazoles (thiazole) are also used for this purpose. Nitroheterocycles may be reductively activated in hypoxic cells, and then undergo redox recycling or decompose to toxic products.