Nitroimidazole

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

Nitroimidazolesare the group oforganic compoundsconsisting of animidazolering with at least onenitro groupsubstituent. The term also refers to the class of antibiotics that have nitroimidazole in their structures.^[2]These antibiotics commonly include the 5-nitroimidazolepositional isomer.

Synthesis[edit]

Imidazoleundergoes anitrationreaction with a mixture ofnitric acidandsulfuric acidto give 5-nitroimidazole.

Nitroimidazole antibiotics[edit]

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 includebenznidazoleandazomycin.^[3]

Nitroimidazole antibiotics have been used to combatanaerobic bacterialandparasitic infections.^[4]Perhaps the most common example ismetronidazole.Other heterocycles such as nitrothiazoles (thiazole) are also used for this purpose. Nitroheterocycles may bereductivelyactivated inhypoxiccells, and then undergoredoxrecycling ordecomposeto toxic products.^[5]

References[edit]

^4-NitroimidazoleatSigma-Aldrich
^Edwards, David I. (1993). "Nitroimidazole drugs-action and resistance mechanisms I. Mechanism of action".Journal of Antimicrobial Chemotherapy.31(1): 9–20.doi:10.1093/jac/31.1.9.PMID 8444678.
^Jenks, Peter J. (2010-01-01), Finch, Roger G.; Greenwood, David; Norrby, S. Ragnar; Whitley, Richard J. (eds.),"CHAPTER 24 - Nitroimidazoles",Antibiotic and Chemotherapy (Ninth Edition),London: W.B. Saunders, pp. 292–300,doi:10.1016/b978-0-7020-4064-1.00024-5,ISBN 978-0-7020-4064-1,retrieved2023-10-18
^Mital A (2009)."Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships".Sci Pharm.77(3): 497–520.doi:10.3797/scipharm.0907-14.
^Juchau, MR (1989). "Bioactivation in chemical teratogenesis".Annu. Rev. Pharmacol. Toxicol.29:165–167.doi:10.1146/annurev.pa.29.040189.001121.PMID 2658769.

[1] 4-NitroimidazoleatSigma-Aldrich

[2] Edwards, David I. (1993). "Nitroimidazole drugs-action and resistance mechanisms I. Mechanism of action".Journal of Antimicrobial Chemotherapy.31(1): 9–20.doi:10.1093/jac/31.1.9.PMID 8444678.

[3] Jenks, Peter J. (2010-01-01), Finch, Roger G.; Greenwood, David; Norrby, S. Ragnar; Whitley, Richard J. (eds.),"CHAPTER 24 - Nitroimidazoles",Antibiotic and Chemotherapy (Ninth Edition),London: W.B. Saunders, pp. 292–300,doi:10.1016/b978-0-7020-4064-1.00024-5,ISBN 978-0-7020-4064-1,retrieved2023-10-18

[Mital2009-4] Mital A (2009)."Synthetic Nitroimidazoles: Biological Activities and Mutagenicity Relationships".Sci Pharm.77(3): 497–520.doi:10.3797/scipharm.0907-14.

[5] Juchau, MR (1989). "Bioactivation in chemical teratogenesis".Annu. Rev. Pharmacol. Toxicol.29:165–167.doi:10.1146/annurev.pa.29.040189.001121.PMID 2658769.

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