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
Elimination half-life	12-13 hours
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;
DrugBank	DB13026 ;
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 ;
	(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] Ornidazole is nothing but chloro-secnidazole.

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

^ ^a ^b ^c ^d Kuhlmann FM, Fleckenstein JM (2017-01-01). "157 - Antiparasitic Agents". In Cohen J, Powderly WG, Opal SM (eds.). Infectious Diseases (Fourth ed.). Elsevier. pp. 1345–1372.e2. doi:10.1016/B978-0-7020-6285-8.00157-X. ISBN 978-0-7020-6285-8.
^ Sharma S, Anand N (January 1997). "Chapter 17 - Nitroheterocycles". In Sharma S, Anand N (eds.). Pharmacochemistry Library. Approaches to Design and Synthesis of Antiparasitic Drugs. Vol. 25. Elsevier. p. 428. doi:10.1016/S0165-7208(97)80039-6. ISBN 9780444894762.
^ Nagel JL, Aronoff DM (January 2015). "28 - Metronidazole". In Bennett JE, Dolin R, Blaser MJ (eds.). Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases (Eighth ed.). Content Repository Only!. p. 356. ISBN 978-1-4557-4801-3.
^ Wilcox MH (January 2017), "147 - Nitroimidazoles, Metronidazole, Ornidazole and Tinidazole; and Fidaxomicin", in Cohen J, Powderly WG, Opal SM (eds.), Infectious Diseases (Fourth ed.), Elsevier, pp. 1261–1263.e1, ISBN 978-0-7020-6285-8
^ Rutgeerts P, Van Assche G, Vermeire S, D'Haens G, Baert F, Noman M, et al. (April 2005). "Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial". Gastroenterology. 128 (4): 856–861. doi:10.1053/j.gastro.2005.01.010. PMID 15825069.

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[:0-1] Kuhlmann FM, Fleckenstein JM (2017-01-01). "157 - Antiparasitic Agents". In Cohen J, Powderly WG, Opal SM (eds.). Infectious Diseases (Fourth ed.). Elsevier. pp. 1345–1372.e2. doi:10.1016/B978-0-7020-6285-8.00157-X. ISBN 978-0-7020-6285-8.

[2] Sharma S, Anand N (January 1997). "Chapter 17 - Nitroheterocycles". In Sharma S, Anand N (eds.). Pharmacochemistry Library. Approaches to Design and Synthesis of Antiparasitic Drugs. Vol. 25. Elsevier. p. 428. doi:10.1016/S0165-7208(97)80039-6. ISBN 9780444894762.

[3] Nagel JL, Aronoff DM (January 2015). "28 - Metronidazole". In Bennett JE, Dolin R, Blaser MJ (eds.). Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases (Eighth ed.). Content Repository Only!. p. 356. ISBN 978-1-4557-4801-3.

[4] Wilcox MH (January 2017), "147 - Nitroimidazoles, Metronidazole, Ornidazole and Tinidazole; and Fidaxomicin", in Cohen J, Powderly WG, Opal SM (eds.), Infectious Diseases (Fourth ed.), Elsevier, pp. 1261–1263.e1, ISBN 978-0-7020-6285-8

[pmid15825069-5] Rutgeerts P, Van Assche G, Vermeire S, D'Haens G, Baert F, Noman M, et al. (April 2005). "Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial". Gastroenterology. 128 (4): 856–861. doi:10.1053/j.gastro.2005.01.010. PMID 15825069.

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v t e Antibacterials: others (J01X, D06AX)
Glycopeptides Lipoglycopeptides	Avoparcin Corbomycin Dalbavancin Oritavancin Ristocetin Teicoplanin Telavancin Vancomycin
Polymyxins	Colistin Polymyxin B
Steroid antibacterials	Fusidic acid
Imidazole derivatives	Metronidazole Ornidazole Tinidazole
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin
Nitrofuran derivatives	Furazolidone Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin Nitrofurazone
Other antibacterials	Bacitracin Clofoctol Daptomycin Fosfomycin Furaltadone Lefamulin Linezolid Mandelic acid Methenamine Nitroxoline Novobiocin Spectinomycin Tedizolid Xibornol