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

Details

Stereochemistry RACEMIC
Molecular Formula C7H10ClN3O3
Molecular Weight 219.626
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

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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
Unknown

Approved Use

Unknown
Curative
Ornidazole

Approved Use

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

PubMed

TitleDatePubMed
Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants.
1992
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Giardiasis treatment in Turkish children with a single dose of ornidazole.
2002
Naegleria meningitis: a rare survival.
2002 Dec
[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
[Clinical features of giardiasis in children and efficacy of tiberal used for their treatment].
2002 Oct-Dec
Flow-injection determination of ornidazole by chemiluminescence detection based on a luminol-ferricyanide reaction.
2003 Apr
A randomized controlled trial of a new ovule formulation of ornidazole for the treatment of bacterial vaginosis.
2003 Apr
On the hydrolytic behavior of tinidazole, metronidazole, and ornidazole.
2003 Apr
Studies on the development of colon targeted oral drug delivery systems for ornidazole in the treatment of amoebiasis.
2003 Apr-Jun
Immunocytochemical localization of DJ-1 in human male reproductive tissue.
2003 Dec
[Randomized, prospective and comparative clinical trial of piperacillin/tazobactam versus ceftriaxone plus ornidazole in the treatment of biliary tract infections].
2003 Dec 6
Strategies in the prevention of post-operative recurrence in Crohn's disease.
2003 Feb
Nitroheterocyclic drugs with broad spectrum activity.
2003 Jun
Review article: prevention of postsurgical relapse and recurrence in Crohn's disease.
2003 Jun
Giardia intestinalis.
2003 Oct
Recent developments in the pharmacological treatment of Crohn's disease.
2004 Apr
Validation of LC/MS electrospray ionisation method for the estimation of ursodiol in human plasma and its application in bioequivalence study.
2004 Dec
Hamster contraception associated protein 1 (CAP1).
2004 Jul
The efficacy of some drugs with known antiprotozoal activity against Histomonas meleagridis in chickens.
2004 May 26
Comparative in vitro cytotoxic effects of ornidazole, metronidazole and ciprofloxacin against Trichomonas vaginalis trophozoites.
2004 Oct
Treatment of postoperative Crohn's disease.
2005
Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial.
2005 Apr
Optochemical sensor for an ornidazole assay using 1-amino-4-allyloxyanthraquinone as a fluorescent indicator.
2005 Aug
Amoebic dysentery.
2005 Dec
[Effect of ornidazole on sperm in rats and its mechanism of action].
2005 Jan
Simultaneous determination of metronidazole and spiramycin I in human plasma, saliva and gingival crevicular fluid by LC-MS/MS.
2005 Jun 15
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
[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
In vivo and real time determination of ornidazole and tinidazole and pharmacokinetic study by capillary electrophoresis with microdialysis.
2006 Jun 16
Treatment of rheumatoid arthritis with ornidazole. A randomized, double-blind, placebo-controlled study.
2006 May
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
Effect of rifampicin pretreatment on the transport across rat intestine and oral pharmacokinetics of ornidazole in healthy human volunteers.
2007
Nonoperative treatment of acute appendicitis in children.
2007 Aug
[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
Simultaneous determination of seven nitroimidazole residues in meat by using HPLC-UV detection with solid-phase extraction.
2007 Oct 1
Determination of tumour hypoxia with the PET tracer [18F]EF3: improvement of the tumour-to-background ratio in a mouse tumour model.
2007 Sep
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
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
Patents

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
Ornidazole minimum lethal concentration against Dientamoeba fragilis: 8 to 16 μg/ml
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:25:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:19 GMT 2023
Record UNII
62XCK0G93T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORNIDAZOLE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official 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
α-(Chloromethyl)-2-methyl-5-nitroimidazole-1-ethanol
Systematic Name English
Ornidazole [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QP51AA03
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-ATC J01RA09
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-ATC J01RA05
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-ATC G01AF06
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-ATC P01AB03
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-VATC QJ01XD03
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-VATC QJ01RA05
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-VATC QG01AF06
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-ATC J01RA12
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
WHO-ATC J01XD03
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
Code System Code Type Description
RXCUI
7701
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
1997
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
WIKIPEDIA
ORNIDAZOLE
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
SMS_ID
100000092163
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL1449676
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
MESH
D009950
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
FDA UNII
62XCK0G93T
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
INN
3319
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
CAS
16773-42-5
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
CHEBI
75176
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
NSC
95075
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
EVMPD
SUB09464MIG
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
DRUG BANK
DB13026
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
MERCK INDEX
m8237
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4045420
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
PUBCHEM
28061
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
240-826-0
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
NCI_THESAURUS
C166891
Created by admin on Fri Dec 15 15:25:19 GMT 2023 , Edited by admin on Fri Dec 15 15:25:19 GMT 2023
PRIMARY
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