Ornidazole

Ornidazole
Clinical data
Trade namesXynor
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Pharmacokinetic data
MetabolismVia liver[1]: 1356 
Elimination half-life12-13 hours[1]: 1356 
ExcretionUrine (63%) and Feces (22%)
Identifiers
IUPAC name
  • 1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.037.099
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Chemical and physical data
FormulaC7H10ClN3O3
Molar mass219.63 g·mol−1
3D model (JSmol)
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 checkY
  • Key:IPWKIXLWTCNBKN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ornidazole is an antibiotic used to treat protozoan infections.[1]: 1368  A synthetic nitroimidazole, it is commercially obtained from an acid-catalyzed reaction between 2-methyl-5-nitroimidazole and epichlorohydrin.[2] Antimicrobial spectrum is similar to that of metronidazole and is more well tolerated;[1]: 1368  however there are concerns of lower relative efficacy.[3]

It was first introduced for treating trichomoniasis before being recognized for its broad anti-protozoan and anti-anaerobic-bacterial capacities.[4]: 1261  has also been investigated for use in Crohn's disease after bowel resection.[5]

References

  1. 1 2 3 4 Kuhlmann, F. Matthew; Fleckenstein, James M. (2017-01-01), Cohen, Jonathan; Powderly, William G.; Opal, Steven M. (eds.), "157 - Antiparasitic Agents", Infectious Diseases (Fourth Edition), Elsevier, pp. 1345–1372.e2, ISBN 978-0-7020-6285-8, retrieved 2020-01-12
  2. ↑ Sharma, Satyavan; Anand, Nitya (1997-01-01), Sharma, Satyavan; Anand, Nitya (eds.), "Chapter 17 - Nitroheterocycles", Pharmacochemistry Library, Approaches to Design and Synthesis of Antiparasitic Drugs, Elsevier, vol. 25, p. 428, retrieved 2020-01-12
  3. ↑ Nagel, Jerod L.; Aronoff, David M. (2015-01-01), Bennett, John E.; Dolin, Raphael; Blaser, Martin J. (eds.), "28 - Metronidazole", Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases (Eighth Edition), Content Repository Only!, p. 356, ISBN 978-1-4557-4801-3, retrieved 2020-01-12
  4. ↑ Wilcox, Mark H. (2017-01-01), Cohen, Jonathan; Powderly, William G.; Opal, Steven M. (eds.), "147 - Nitroimidazoles, Metronidazole, Ornidazole and Tinidazole; and Fidaxomicin", Infectious Diseases (Fourth Edition), Elsevier, pp. 1261–1263.e1, ISBN 978-0-7020-6285-8, retrieved 2020-01-12
  5. ↑ 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.


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