Nitroimidazole

5-Nitroimidazole[1]
IUPAC name 5-Nitro-1H-imidazole
Identifiers
CAS number	100214-79-7 Y
PubChem	18208
ChemSpider	10637918 Y
Jmol-3D images	Image 1
SMILES c1cn(cn1)[N+](=O)[O-]
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
Properties
Molecular formula	C3H3N3O2
Molar mass	113.07 g/mol
Melting point	303 °C (dec.)
Hazards
R-phrases	R20/21/22 R36/37/38
S-phrases	S26 S36/37
Main hazards	Xn
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

5-Nitroimidazole is an imidazole derivative that contains a nitro group.

Several derivatives of nitroimidazole constitute the class of nitroimidazole antibiotics that have been used to combat anaerobic bacterial and parasitic infections.^[2] Perhaps the most common example is metronidazole (Flagyl). 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.^[3]

Three nitroimidazoles: metronidazole, tinidazole, and nimorazole

References