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
Nitroimidazole-induced chronic hepatitis.
2001 Aug
Chronic Giardia intestinalis infection presenting with clinical features mimicking lichen planus.
2001 Aug-Sep
The ICH guidance in practice: stress degradation studies on ornidazole and development of a validated stability-indicating assay.
2001 Dec
[Systemic antimicrobial treatment of prosthesis related infections: a comparative study of ornidazole and minocycline. A microbiological evaluation and experimental protocol].
2001 Jun
Ornidazole-induced autoimmune hepatitis.
2001 Jun
Giardiasis treatment in Turkish children with a single dose of ornidazole.
2002
Naegleria meningitis: a rare survival.
2002 Dec
[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
Review article: prevention of postsurgical relapse and recurrence in Crohn's disease.
2003 Jun
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
Acute neck infections in children.
2004 Apr-Jun
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
Optochemical sensor for an ornidazole assay using 1-amino-4-allyloxyanthraquinone as a fluorescent indicator.
2005 Aug
[Effect of ornidazole on sperm in rats and its mechanism of action].
2005 Jan
Radiosynthesis and evaluation of two novel 123I-labeled 2-methyl-4-nitroimidazole derivatives as potential infection imaging agents.
2005 May
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
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
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
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
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
Nonoperative treatment of acute appendicitis in children.
2007 Aug
Nitroimidazole action in Entamoeba histolytica: a central role for thioredoxin reductase.
2007 Aug
[Post-traumatic necrotizing fasciitis].
2007 Jan
Study on poly(vinyl alcohol)/carboxymethyl-chitosan blend film as local drug delivery system.
2007 Jun
[Investigation of Aspergillus galactomannan levels in antimicrobial agents].
2007 Oct
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
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

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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