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Ornidazole

Ornidazole
Ornidazole.svg
Clinical data
Trade namesXynor
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Pharmacokinetic data
MetabolismMetabolized via the liver, excreted in the Urine and Feces
Excretion85% of single oral dose is eliminated with 5 days - Urine (63%) and Feces (22%)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.037.099 Edit this at Wikidata
Chemical and physical data
FormulaC7H10ClN3O3
Molar mass219.63 g·mol−1
3D model (JSmol)
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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

  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.
  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. ^ [webcache.googleusercontent.com]