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	Via liver[1]
Elimination half-life	12-13 hours[1]
Excretion	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 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

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
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, 25, p. 428, retrieved 2020-01-12
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
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
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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[:0-1] 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, 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

[pmid15825069-5] 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.