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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

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
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
[Septic thrombophlebitis of the portal vein associated with reversible portal hypertension].
2001
Ornidazole treatment in normal subjects reduces serum levels of C3.
2001 Apr
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
[Aseptic meningitis ornidazole-induced in the course of infectious endocarditis].
2002 Sep
Flow-injection determination of ornidazole by chemiluminescence detection based on a luminol-ferricyanide reaction.
2003 Apr
Strategies in the prevention of post-operative recurrence in Crohn's disease.
2003 Feb
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
Dissolution and vaginal absorption characteristics of metronidazole and ornidazole.
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
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
[Post-traumatic necrotizing fasciitis].
2007 Jan
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
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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:25:19 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-ATC J01RA09
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-ATC J01RA05
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-ATC G01AF06
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-ATC P01AB03
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-VATC QJ01XD03
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-VATC QJ01RA05
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-VATC QG01AF06
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-ATC J01RA12
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
WHO-ATC J01XD03
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
Code System Code Type Description
RXCUI
7701
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
1997
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
WIKIPEDIA
ORNIDAZOLE
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
SMS_ID
100000092163
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL1449676
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
MESH
D009950
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
FDA UNII
62XCK0G93T
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
INN
3319
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
CAS
16773-42-5
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
CHEBI
75176
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
NSC
95075
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
EVMPD
SUB09464MIG
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
DRUG BANK
DB13026
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
MERCK INDEX
m8237
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4045420
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
PUBCHEM
28061
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
240-826-0
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
NCI_THESAURUS
C166891
Created by admin on Fri Dec 15 15:25:19 UTC 2023 , Edited by admin on Fri Dec 15 15:25:19 UTC 2023
PRIMARY
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