U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Ornidazole
Preventing
Unknown
Curative
Ornidazole

Cmax

ValueDoseCo-administeredAnalytePopulation
16185 ng/mL
1000 mg single, oral
ORNIDAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
332948 ng × h/mL
1000 mg single, oral
ORNIDAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.7 h
1000 mg single, oral
ORNIDAZOLE plasma
Homo sapiens
13 h
unknown
ORNIDAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
87%
unknown
ORNIDAZOLE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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: Other
In Vitro Use Guide
Ornidazole minimum lethal concentration against Dientamoeba fragilis: 8 to 16 μg/ml