U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C7H10ClN3O3
Molecular Weight 219.6258
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORNIDAZOLE

SMILES

Cc1ncc(n1CC(CCl)O)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
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Ornidazole

Approved Use

Indications for Ornidazole 1.Amoebiasis 2.Giardiasis 3.Trichomonas vaginitis 4.Anaerobic bacterial infections 5.Bacterial vaginosis
Preventing
Curative
Ornidazole

Approved Use

Indications for Ornidazole 1.Amoebiasis 2.Giardiasis 3.Trichomonas vaginitis 4.Anaerobic bacterial infections 5.Bacterial vaginosis
PubMed

PubMed

TitleDatePubMed
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Chronic Giardia intestinalis infection presenting with clinical features mimicking lichen planus.
2001 Aug-Sep
Overview of studies on rat sperm motion analysis using a Hamilton-Thorne Sperm Analyzer--collaborative working study.
2001 Dec
The ICH guidance in practice: stress degradation studies on ornidazole and development of a validated stability-indicating assay.
2001 Dec
Giardiasis treatment in Turkish children with a single dose of ornidazole.
2002
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
Naegleria meningitis: a rare survival.
2002 Dec
Inflammatory bowel disease.
2002 Dec 12
DJ-1, a target protein for an endocrine disrupter, participates in the fertilization in mice.
2002 Jul
DNA single strand breaks in peripheral blood lymphocytes induced by three nitroimidazole derivatives.
2002 Jun 14
[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
Flow-injection determination of ornidazole by chemiluminescence detection based on a luminol-ferricyanide reaction.
2003 Apr
On the hydrolytic behavior of tinidazole, metronidazole, and ornidazole.
2003 Apr
Strategies in the prevention of post-operative recurrence in Crohn's disease.
2003 Feb
Review article: prevention of postsurgical relapse and recurrence in Crohn's disease.
2003 Jun
Ornidazole-induced liver damage: report of three cases and review of the literature.
2003 Oct
Teratogenic evaluation of metronidazole and ornidazole using Drosophila melanogaster as an experimental model.
2004 Apr
Recent developments in the pharmacological treatment of Crohn's disease.
2004 Apr
Hamster contraception associated protein 1 (CAP1).
2004 Jul
Amoebic dysentery.
2005 Dec
Radiosynthesis and evaluation of two novel 123I-labeled 2-methyl-4-nitroimidazole derivatives as potential infection imaging agents.
2005 May
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
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
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
Dissolution and vaginal absorption characteristics of metronidazole and ornidazole.
2006 Oct
Review article: can post-operative recurrence in Crohn's disease be prevented?
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
Severe hepatitis with prolonged cholestasis and bile duct injury due the long-term use of ornidazole.
2007 Jul-Sep
[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
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
Patents

Sample Use Guides

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 Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-ATC J01RA09
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-ATC J01RA05
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-ATC G01AF06
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-ATC P01AB03
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-VATC QJ01XD03
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-VATC QJ01RA05
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-VATC QG01AF06
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-ATC J01RA12
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
WHO-ATC J01XD03
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
Code System Code Type Description
RXCUI
7701
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1997
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
WIKIPEDIA
ORNIDAZOLE
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
ChEMBL
CHEMBL1449676
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
MESH
D009950
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
FDA UNII
62XCK0G93T
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
INN
3319
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
CAS
16773-42-5
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
EVMPD
SUB09464MIG
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
DRUG BANK
DB13026
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
MERCK INDEX
M8237
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY Merck Index
PUBCHEM
28061
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
240-826-0
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY
NCI_THESAURUS
C166891
Created by admin on Sat Jun 26 10:58:26 UTC 2021 , Edited by admin on Sat Jun 26 10:58:26 UTC 2021
PRIMARY