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]^: 1356
Elimination half-life	12-13 hours^[1]^: 1356
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^Y
PubChem CID	28061
DrugBank	DB13026^Y
ChemSpider	26102^Y
UNII	62XCK0G93T
KEGG	D05274^Y
ChEBI	CHEBI:75176^N
ChEMBL	ChEMBL1449676^N
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^Y Key:IPWKIXLWTCNBKN-UHFFFAOYSA-N^Y
^NY (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.

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

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole
Triazoles	Terconazole
Polyenes	Nystatin Natamycin Amphotericin B
Other	Ciclopirox Methylrosaniline

Other

Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)

Entamoeba

Tissue amebicides

Nitroimidazole derivatives	Metronidazole^# Tinidazole Ornidazole Nimorazole Secnidazole Azanidazole Propenidazole
Other	isoquinoline (Emetine/Dehydroemetine)

Luminal amebicides

Hydroxyquinoline derivatives	Cl (Chlorquinaldol) Br (Tilbroquinol Broxyquinoline) I (Diiodohydroxyquinoline) I, Cl (Clioquinol) related: Chiniofon
Dichloroacetamide derivatives	Diloxanide^# Clefamide Etofamide Teclozan
Aminoglycoside	Paromomycin^#

Other/ungrouped

Acanthamoeba

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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