Ornidazole

Ornidazole
Clinical data
Trade names	Xynor
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	G01AF06 (WHO) J01XD03 (WHO) P01AB03 (WHO) QP51AA03 (WHO);
Pharmacokinetic data
Metabolism	Metabolized via the liver, excreted in the Urine and Feces
Excretion	85% of single oral dose is eliminated with 5 days - Urine (63%) and Feces (22%)
Identifiers
	IUPAC name 1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol;
CAS Number	16773-42-5 ;
PubChem CID	28061;
ChemSpider	26102 ;
UNII	62XCK0G93T;
KEGG	D05274 ;
ChEBI	CHEBI:75176 ;
ChEMBL	ChEMBL1449676 ;
CompTox Dashboard (EPA)	DTXSID4045420 ;
ECHA InfoCard	100.037.099
Chemical and physical data
Formula	C7H10ClN3O3
Molar mass	219.63 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c1cnc(n1CC(O)CCl)C;
	InChI InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3 ; Key:IPWKIXLWTCNBKN-UHFFFAOYSA-N ;
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Ornidazole is an antibiotic used to treat some protozoan infections. It has also been investigated for use in Crohn's disease after bowel resection.[1]

Synthesis is a straightforward reaction between 2-methyl-nitroimidazole and epichlorohydrin under acid catalyst conditions.[2]

Mechanism of action and susceptible organisms

After passive absorption into bacterium cell, the nitro group of ornidazole is reduced to an amine group by ferrodoxin-type redox systems. The formation of redox intermediate intracellular metabolites is believed to be the key component responsible for killing microorganisms. The drug is active against anaerobic bacteria including Peptostreptococcus, Clostridium, Bacteroides fragilis, Prevotella, Porphyromonas gingivalis, and Fusobacterium as well as protozoa including Entamoeba histolytica, Trichomonas vaginalis, and Giardia lamblia.[3]

References

Rutgeerts P, Van Assche G, Vermeire S, et al. (April 2005). "Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial". Gastroenterology. 128 (4): 856–61. doi:10.1053/j.gastro.2005.01.010. PMID 15825069.
Hoffer, Max; Grunberg, Emanuel (1974). "Synthesis and antiprotozoal activity of 1-(3-chloro-2-hydroxypropyl)-substituted nitroimidazoles". Journal of Medicinal Chemistry. 17 (9): 1019–1020. doi:10.1021/jm00255a026. ISSN 0022-2623.
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[pmid15825069-1] Rutgeerts P, Van Assche G, Vermeire S, et al. (April 2005). "Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial". Gastroenterology. 128 (4): 856–61. doi:10.1053/j.gastro.2005.01.010. PMID 15825069.

[HofferGrunberg1974-2] Hoffer, Max; Grunberg, Emanuel (1974). "Synthesis and antiprotozoal activity of 1-(3-chloro-2-hydroxypropyl)-substituted nitroimidazoles". Journal of Medicinal Chemistry. 17 (9): 1019–1020. doi:10.1021/jm00255a026. ISSN 0022-2623.

[3] ttp://webcache.googleusercontent.com/search?q=cache:OFkC_pjHLZ4J:www.panacea-biotec.com/product-pdf/Ocimix_28-11-2010.pdf