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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
Structure of ORNIDAZOLE

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

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
Ornidazole
Primary
Ornidazole
Preventing
PMID

PMID

TitleDatePMID
[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
Amoebic dysentery.
2005 Dec
Fixed drug eruption caused by ornidazole.
2005 Nov
A multicenter point-prevalence study: antimicrobial prescription frequencies in hospitalized patients in Turkey.
2005 Oct 3
Antispermatogenic activity of the benzothiazoline ligand and corresponding organoantimony(V) derivative in male albino rats.
2006
Effect of ketoconazole on the pharmacokinetics of ornidazole--a possible role of p-glycoprotein and CYP3A.
2006
Bioadhesive controlled release systems of ornidazole for vaginal delivery.
2006
[Clinical and microbiological efficacy of metronidazole and ornidazole in the treatment of urogenital trichomoniasis in men].
2006
Febrile neutropenia as the presenting sign of appendicitis in an adolescent with acute myelogenous leukemia.
2006 Apr-May
Chiral separation of rac-Ornidazole and detection of the impurity of (R)-Ornidazole in (S)-Ornidazole injection and raw material.
2006 Aug
Decreased susceptibility to nitroimidazoles among Bacteroides species in Brazil.
2006 Jan
Postoperative maintenance therapy for inflammatory bowel disease.
2006 Jul
Amoebic dysentery.
2006 Jun
In vivo and real time determination of ornidazole and tinidazole and pharmacokinetic study by capillary electrophoresis with microdialysis.
2006 Jun 16
Determination of gatifloxacin and ornidazole in tablet dosage forms by high-performance thin-layer chromatography.
2006 May
Treatment of rheumatoid arthritis with ornidazole. A randomized, double-blind, placebo-controlled study.
2006 May
[Urokinase-type plasminogen activator improves the reproductive function of male rats].
2006 Nov
Stereoselective pharmacokinetics of ornidazole after intravenous administration of individual enantiomers and the racemate.
2006 Nov
Antimicrobial drug ornidazole inhibits hamster sperm capacitation, in vitro.
2006 Nov
[Postoperative recurrence in Crohn's disease. Risk factors and methods of prevention].
2006 Oct
Dissolution and vaginal absorption characteristics of metronidazole and ornidazole.
2006 Oct
Novel therapies for Crohn's disease: focus on immunomodulators and antibiotics.
2006 Oct
Review article: recurrence of Crohn's disease after surgery - the need for treatment of new lesions.
2006 Oct
Review article: can post-operative recurrence in Crohn's disease be prevented?
2006 Oct
Treatment of rheumatoid arthritis with ornidazole: a randomized, double-blind, placebo-controlled study.
2006 Oct
Kikuchi Fujimoto disease secondary to Entamoeba histolytica: case report.
2006 Oct
Maintenance of surgically induced remission of Crohn's disease.
2007
Effect of rifampicin pretreatment on the transport across rat intestine and oral pharmacokinetics of ornidazole in healthy human volunteers.
2007
The application of resonance light scattering technique for the determination of tinidazole in drugs.
2007
An improved HPLC method for determination of nifuratel in human plasma and its application to pharmacokinetics studies.
2007 Apr-Jun
Nonoperative treatment of acute appendicitis in children.
2007 Aug
Nitroimidazole action in Entamoeba histolytica: a central role for thioredoxin reductase.
2007 Aug
Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study.
2007 Dec
[Post-traumatic necrotizing fasciitis].
2007 Jan
Severe hepatitis with prolonged cholestasis and bile duct injury due the long-term use of ornidazole.
2007 Jul-Sep
Study on poly(vinyl alcohol)/carboxymethyl-chitosan blend film as local drug delivery system.
2007 Jun
W/O/W multiple emulsions containing nitroimidazole derivates for vaginal delivery.
2007 Mar
[Investigation of Aspergillus galactomannan levels in antimicrobial agents].
2007 Oct
Simultaneous determination of seven nitroimidazole residues in meat by using HPLC-UV detection with solid-phase extraction.
2007 Oct 1
Validated HPTLC method for simultaneous estimation of levofloxacin hemihydrate and ornidazole in pharmaceutical dosage form.
2007 Sep
Determination of tumour hypoxia with the PET tracer [18F]EF3: improvement of the tumour-to-background ratio in a mouse tumour model.
2007 Sep
Some drugs inhibit in vitro hydratase and esterase activities of human carbonic anhydrase-I and II.
2007 Sep-Oct
SodiumPhosphate (NaP) versus polyethylene glycol-electrolyte lavage solution (PEG-ELS) tolerability: a prospective randomized study in patients with gynecological malignancy.
2008
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
Effects of some antibiotics on human erythrocyte glutathione reductase: an in vitro study.
2008 Feb
Laparoscopic management of symptomatic Meckel's diverticula: a simple tangential stapler excision.
2008 Jan-Mar
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
Laparoscopic restorative total proctocolectomy with ileal pouch anal anastomosis for familial adenomatous polyposis.
2008 Jul-Sep
A comparison of metronidazole and single-dose ornidazole for the treatment of dientamoebiasis.
2008 Jun
Characterization and ornidazole release in vitro of a novel composite film prepared with chitosan/poly(vinyl alcohol)/alginate.
2008 May
Patent

Sample Use Guides

In Vivo Use Guide
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: oral, intravenous
In Vitro Use Guide
Ornidazole minimum lethal concentration against Dientamoeba fragilis: 8 to 16 μg/ml
Name Type Language
ORNIDAZOLE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
ORNIDAZOLE [WHO-DD]
Common Name English
NSC-95075
Code English
ORNIDAZOLE [MI]
Common Name English
RO-7-0207
Code English
RO 7-0207
Code English
ORNIDAZOLE [USAN]
Common Name English
ORNIDAZOLE [INN]
Common Name English
RO-70207
Code English
ORNIDAZOLE [MART.]
Common Name English
1H-IMIDAZOLE-1-ETHANOL, .ALPHA.-(CHLOROMETHYL)-2-METHYL-5-NITRO-
Systematic Name English
.ALPHA.-(CHLOROMETHYL)-2-METHYL-5-NITROIMIDAZOLE-1-ETHANOL
Systematic Name English
Classification Tree Code System Code
WHO-VATC QP51AA03
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-ATC J01RA09
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-ATC J01RA05
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-ATC G01AF06
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-ATC P01AB03
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-VATC QJ01XD03
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-VATC QJ01RA05
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-VATC QG01AF06
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-ATC J01RA12
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
WHO-ATC J01XD03
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
Code System Code Type Description
RXCUI
7701
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY RxNorm
WIKIPEDIA
ORNIDAZOLE
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY
ChEMBL
CHEMBL1449676
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY
MESH
D009950
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY
INN
3319
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY
CAS
16773-42-5
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY
EVMPD
SUB09464MIG
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY
MERCK INDEX
M8237
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY Merck Index
PUBCHEM
28061
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY SWITZERF
ECHA (EC/EINECS)
240-826-0
Created by admin on Tue Mar 06 17:13:26 UTC 2018 , Edited by admin on Tue Mar 06 17:13:26 UTC 2018
PRIMARY