Nitroimidazole

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5-Nitroimidazole[1]
4-Nitroimidazole.png
Identifiers
CAS number 100214-79-7 YesY
PubChem 18208
ChemSpider 10637918 YesY
Jmol-3D images Image 1
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

  1. ^ 4-Nitroimidazole at Sigma-Aldrich
  2. ^ Mital A (2009). "Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships". Sci Pharm 77 (3): 497–520. doi:10.3797/scipharm.0907-14. 
  3. ^ Juchau, MR (1989). "Bioactivation in chemical teratogenesis". Annu. Rev. Pharmacol. Toxicol. 29: 165–167. doi:10.1146/annurev.pa.29.040189.001121. PMID 2658769.