Details
Stereochemistry | RACEMIC |
Molecular Formula | C7H10ClN3O3 |
Molecular Weight | 219.626 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NC=C(N1CC(O)CCl)[N+]([O-])=O
InChI
InChIKey=IPWKIXLWTCNBKN-UHFFFAOYSA-N
InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3
Molecular Formula | C7H10ClN3O3 |
Molecular Weight | 219.626 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Ornidazole is nitroimidazole derivative. It is an antiprotozoal drug that has proven to be effective against Trichomonas vaginalis, Entoamoeba histolytica, Giardia lamblia and Helicobacter pylori. The reduction of the nitro group and the generation of short-lived reactive intermediates are the basis of its parasiticidal activity. Ornidazole is a DNA-tropic drug with selective activity against microorganisms with enzyme systems capable of reducing the nitrogroup and catalyze the interaction between ferrodoxin proteins and nitrocompounds. After the drug penetrates the microbial cell, the mechanism of its action is based reducing the nitrogroup under the influence of the microorganism’s nitroreductases and the activity of the reduced nitroimidazole. The reduction products create compounds with DNA causing it to degrade, and disrupt the DNA replication and transcription processes. Furthermore, the drug’s metabolism products have cytotoxic properties and disrupt cellular respiration processes. It is indicated for the treatment of anaerobic systemic infections caused by ornidazole-sensitive microflora, prevention of infections caused by anaerobic bacteria, during operative treatment (especially middle and straight intestine surgeries), gynecological surgeries, severe intestinal ameobiasis, all extra-intestinal ameobiasis forms, giardiasis. Ornidazole was shown to be effective for the prevention of recurrence of Crohn's disease after ileocolonic resection.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Ornidazole Approved UseIndications for Ornidazole
1.Amoebiasis
2.Giardiasis
3.Trichomonas vaginitis
4.Anaerobic bacterial infections
5.Bacterial vaginosis |
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Preventing | Unknown Approved UseUnknown |
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Curative | Ornidazole Approved UseIndications for Ornidazole
1.Amoebiasis
2.Giardiasis
3.Trichomonas vaginitis
4.Anaerobic bacterial infections
5.Bacterial vaginosis |
PubMed
Title | Date | PubMed |
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Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
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Ornidazole treatment in normal subjects reduces serum levels of C3. | 2001 Apr |
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Nitroimidazole-induced chronic hepatitis. | 2001 Aug |
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Prevalence of 5-nitroimidazole-resistant trichomonas vaginalis in Oviedo, Spain. | 2001 Feb |
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Giardiasis treatment in Turkish children with a single dose of ornidazole. | 2002 |
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The effect of (R,S)-ornidazole on the fertility of male mice and the excretion and metabolism of 36Cl-(R,S)-ornidazole and 36Cl-(R,S)-alpha-chlorohydrin in male mice and rats. | 2002 Apr |
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DJ-1, a target protein for an endocrine disrupter, participates in the fertilization in mice. | 2002 Jul |
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DNA single strand breaks in peripheral blood lymphocytes induced by three nitroimidazole derivatives. | 2002 Jun 14 |
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[Double blind randomized multicentre study of a seven-day eradication regime of Helicobacter pylori by omeprazole, clarithromycin and ornidazole vs. omeprazole, clarithromycin and metronidazole]. | 2002 Oct |
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[Aseptic meningitis ornidazole-induced in the course of infectious endocarditis]. | 2002 Sep |
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On the hydrolytic behavior of tinidazole, metronidazole, and ornidazole. | 2003 Apr |
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Studies on the development of colon targeted oral drug delivery systems for ornidazole in the treatment of amoebiasis. | 2003 Apr-Jun |
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In vivo evaluation of guar gum-based colon-targeted drug delivery systems of ornidazole in healthy human volunteers. | 2003 Feb |
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Strategies in the prevention of post-operative recurrence in Crohn's disease. | 2003 Feb |
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Nitroheterocyclic drugs with broad spectrum activity. | 2003 Jun |
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Teratogenic evaluation of metronidazole and ornidazole using Drosophila melanogaster as an experimental model. | 2004 Apr |
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Recent developments in the pharmacological treatment of Crohn's disease. | 2004 Apr |
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Acute neck infections in children. | 2004 Apr-Jun |
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Validation of LC/MS electrospray ionisation method for the estimation of ursodiol in human plasma and its application in bioequivalence study. | 2004 Dec |
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Hamster contraception associated protein 1 (CAP1). | 2004 Jul |
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Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial. | 2005 Apr |
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Amoebic dysentery. | 2005 Dec |
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[Effect of ornidazole on sperm in rats and its mechanism of action]. | 2005 Jan |
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Fixed drug eruption caused by ornidazole. | 2005 Nov |
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Antispermatogenic activity of the benzothiazoline ligand and corresponding organoantimony(V) derivative in male albino rats. | 2006 |
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Effect of ketoconazole on the pharmacokinetics of ornidazole--a possible role of p-glycoprotein and CYP3A. | 2006 |
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Bioadhesive controlled release systems of ornidazole for vaginal delivery. | 2006 |
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[Clinical and microbiological efficacy of metronidazole and ornidazole in the treatment of urogenital trichomoniasis in men]. | 2006 |
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Febrile neutropenia as the presenting sign of appendicitis in an adolescent with acute myelogenous leukemia. | 2006 Apr-May |
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Postoperative maintenance therapy for inflammatory bowel disease. | 2006 Jul |
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Amoebic dysentery. | 2006 Jun |
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In vivo and real time determination of ornidazole and tinidazole and pharmacokinetic study by capillary electrophoresis with microdialysis. | 2006 Jun 16 |
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Dissolution and vaginal absorption characteristics of metronidazole and ornidazole. | 2006 Oct |
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Novel therapies for Crohn's disease: focus on immunomodulators and antibiotics. | 2006 Oct |
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Severe hepatitis with prolonged cholestasis and bile duct injury due the long-term use of ornidazole. | 2007 Jul-Sep |
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Study on poly(vinyl alcohol)/carboxymethyl-chitosan blend film as local drug delivery system. | 2007 Jun |
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W/O/W multiple emulsions containing nitroimidazole derivates for vaginal delivery. | 2007 Mar |
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Some drugs inhibit in vitro hydratase and esterase activities of human carbonic anhydrase-I and II. | 2007 Sep-Oct |
Sample Use Guides
Typical Dosage for Ornidazole
Amoebiasis:
Adults: 1gm daily in 2 divided doses for 7 to 10 days
Children: 10 to 25mg/kg once daily for 3days
Amoebic dysentery:
Adults: 1.5gm once daily for 3 days
Children: 40mg/kg once daily for 3 days
Trichomoniasis
Adults: 1.5gm single daily dose or 0.5gm 12hourly for 5 days,
Male partner should be concurrently treated.
Children: 25mg/kg as a single dose
Giardiasis:
Adults: 1 to 1.5gm once daily for 2days
Children: 40mg/kg for 2days
Bacterial vaginosis: 1.5gm once or 500mg once daily for 5 to7 days
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22024820
Ornidazole minimum lethal concentration against Dientamoeba fragilis: 8 to 16 μg/ml
Substance Class |
Chemical
Created
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