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 |
---|---|---|---|
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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Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants. | 1992 |
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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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Giardiasis treatment in Turkish children with a single dose of ornidazole. | 2002 |
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Naegleria meningitis: a rare survival. | 2002 Dec |
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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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[Clinical features of giardiasis in children and efficacy of tiberal used for their treatment]. | 2002 Oct-Dec |
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Flow-injection determination of ornidazole by chemiluminescence detection based on a luminol-ferricyanide reaction. | 2003 Apr |
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A randomized controlled trial of a new ovule formulation of ornidazole for the treatment of bacterial vaginosis. | 2003 Apr |
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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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Immunocytochemical localization of DJ-1 in human male reproductive tissue. | 2003 Dec |
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[Randomized, prospective and comparative clinical trial of piperacillin/tazobactam versus ceftriaxone plus ornidazole in the treatment of biliary tract infections]. | 2003 Dec 6 |
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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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Review article: prevention of postsurgical relapse and recurrence in Crohn's disease. | 2003 Jun |
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Giardia intestinalis. | 2003 Oct |
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Recent developments in the pharmacological treatment of Crohn's disease. | 2004 Apr |
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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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The efficacy of some drugs with known antiprotozoal activity against Histomonas meleagridis in chickens. | 2004 May 26 |
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Comparative in vitro cytotoxic effects of ornidazole, metronidazole and ciprofloxacin against Trichomonas vaginalis trophozoites. | 2004 Oct |
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Treatment of postoperative Crohn's disease. | 2005 |
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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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Optochemical sensor for an ornidazole assay using 1-amino-4-allyloxyanthraquinone as a fluorescent indicator. | 2005 Aug |
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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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Simultaneous determination of metronidazole and spiramycin I in human plasma, saliva and gingival crevicular fluid by LC-MS/MS. | 2005 Jun 15 |
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A multicenter point-prevalence study: antimicrobial prescription frequencies in hospitalized patients in Turkey. | 2005 Oct 3 |
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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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[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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Chiral separation of rac-Ornidazole and detection of the impurity of (R)-Ornidazole in (S)-Ornidazole injection and raw material. | 2006 Aug |
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Decreased susceptibility to nitroimidazoles among Bacteroides species in Brazil. | 2006 Jan |
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Postoperative maintenance therapy for inflammatory bowel disease. | 2006 Jul |
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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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Treatment of rheumatoid arthritis with ornidazole. A randomized, double-blind, placebo-controlled study. | 2006 May |
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Treatment of rheumatoid arthritis with ornidazole: a randomized, double-blind, placebo-controlled study. | 2006 Oct |
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Kikuchi Fujimoto disease secondary to Entamoeba histolytica: case report. | 2006 Oct |
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Effect of rifampicin pretreatment on the transport across rat intestine and oral pharmacokinetics of ornidazole in healthy human volunteers. | 2007 |
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Nonoperative treatment of acute appendicitis in children. | 2007 Aug |
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[Post-traumatic necrotizing fasciitis]. | 2007 Jan |
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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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Simultaneous determination of seven nitroimidazole residues in meat by using HPLC-UV detection with solid-phase extraction. | 2007 Oct 1 |
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Determination of tumour hypoxia with the PET tracer [18F]EF3: improvement of the tumour-to-background ratio in a mouse tumour model. | 2007 Sep |
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SodiumPhosphate (NaP) versus polyethylene glycol-electrolyte lavage solution (PEG-ELS) tolerability: a prospective randomized study in patients with gynecological malignancy. | 2008 |
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Correlation between CD4 counts of HIV patients and enteric protozoan in different seasons - an experience of a tertiary care hospital in Varanasi (India). | 2008 Aug 20 |
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Development and validation of column high-performance liquid chromatographic and derivative spectrophotometric methods for determination of levofloxacin and ornidazole in combined dosage forms. | 2008 Jul-Aug |
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Laparoscopic restorative total proctocolectomy with ileal pouch anal anastomosis for familial adenomatous polyposis. | 2008 Jul-Sep |
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A comparison of metronidazole and single-dose ornidazole for the treatment of dientamoebiasis. | 2008 Jun |
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
by
admin
on
Edited
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by
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Record UNII |
62XCK0G93T
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Record Status |
Validated (UNII)
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