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Ornidazole, chemical name 1- (3-chloro-2-hydroxypropyl) -2-methyl-5-nitroimidazole, CAS 16773-42-5, The molecular formula C7H10ClN3O3 is a 5-nitroimidazole antibiotic. It is used to treat a variety of infectious diseases caused by sensitive anaerobic bacteria such as Bacteroides fragilis, Bacteroides diricholi, Bacteroides ovalis, Bacteroides polymorphus, Bacteroides vulgaris, Clostridium, Eubacterium, Digestive coccus and Digestive Streptococcus, Helicobacter pylori, Bacteroides melanin, Fusobacterium, CO2 bacteriophage, Bacteroides gingivalis, etc. It can inhibit the growth and reproduction of bacteria, and has bactericidal effects on many different types of bacteria, including anaerobic bacteria and Gram negative bacteria. It is very effective in treating infections of the digestive system, especially intestinal bacteria and amoebic infections that cause diarrhea.
| Chemical Formula | C7H10ClN3O3 |
| Exact Mass | 219 |
| Molecular Weight | 220 |
| m/z | 219 (100.0%), 221 (32.0%), 220 (7.6%), 222 (2.4%), 220 (1.1%) |
| Elemental Analysis | C, 38.28; H, 4.59; Cl, 16.14; N, 19.13; O, 21.85 |
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Pharmacological action
This product is a nitroimidazole derivative, and its mechanism of exerting antimicrobial effects may be through the reduction of nitro groups in its molecules to amino groups in an anaerobic environment or through the formation of free radicals, which interact with cellular components and lead to microbial death.
Toxicological studies
Repeated administration toxicity: Rats were given a dose of 400mg/Kg/day for 2 consecutive years, and there was no effect on the lifespan of the animals, nor did it cause serious functional or morphological changes. When dogs were given a continuous dose of 250mg/Kg/day for one year, central nervous system symptoms appeared, which were observed in rat experiments with nitroimidazole derivatives.
Genetic toxicity: Similar to other nitroimidazole drugs, this product has mutagenic effects on various bacteria, but dominant lethal tests on human lymphocytes and mice have shown that this product has no effect on mammalian cell chromosomes.
Reproductive toxicity: In high-dose studies conducted in rats, mice, and rabbits, there were no significant effects on fetuses and the perinatal period. Rats and mice were administered a dose of 400mg/Kg/day, while rabbits were administered a dose of 100mg/Kg/day, and no teratogenic effects were observed. Oral administration can inhibit the reproductive ability of male rats, but unlike other 5-nitroimidazole compounds, this product does not inhibit sperm production. At present, there is no sufficient and strictly controlled clinical research data on pregnant women. Due to the fact that animal reproductive research cannot fully predict the effects of drugs on humans, this product should only be used during pregnancy when Ornidazole is truly necessary.
Carcinogenicity: When administered to rats at a dose of 400mg/Kg/day for two consecutive years, no carcinogenicity was observed.
Pharmacokinetics
Currently, there is a lack of pharmacokinetic research data on metronidazole injection in China.
The pharmacokinetic studies of metronidazole reported in the literature are as follows:
1) According to the 31st edition of the Martindale Pharmacopoeia (1996 edition), metronidazole is easily absorbed through the gastrointestinal tract. A single dose of 1.5g orally can reach a maximum plasma concentration of approximately 30 μ g/mL within 2 hours, which drops to 9 μ g/mL after 24 hours and 2.5 μ g/mL after 48 hours. Metronidazole is also absorbed through the vagina. According to reports, after local use of 500mg metronidazole vaginal suppositories for 12 hours, the maximum plasma concentration is about 5 μ g/mL.
The plasma elimination half-life of metronidazole is 14 hours, and the plasma protein binding rate is less than 15%. It is widely distributed in tissues and body fluids, including cerebrospinal fluid.
Metronidazole is metabolized in the liver and mainly excreted in urine as conjugates and metabolites, with a small amount excreted in feces. It has been reported that the elimination rate of this product after a single dose oral administration is 85% within 5 days, 63% in urine, and 22% in feces. Bile excretion accounts for approximately 4.1% of the elimination of metronidazole and its metabolites.
2) According to foreign literature reports, a 30 minute intravenous infusion of 1g metronidazole in healthy volunteers has a half-life t1/2 of 14.1 ± 0.5h, an MRT of 19.4 ± 0.6h, a plasma clearance rate of 50.6 ± 2.1ml/min, and a VSS value of 0.86 ± 0.02L/Kg. There are two main metabolites metabolized in the body, M1 (1- (3-chloro-2-propyl) -2-hydroxymethyl-5-nitroimidazole) and M4 (1- (3-hydroxy-2-hydroxypropyl) -2-methyl-5-nitroimidazole). The concentrations of metabolites M1 and M4 are lower than the original drug, and their activities are also much lower than metronidazole. Their cmax are 85 ± 6120 ± 6ng/mL, and t1/2 are 14.4 ± 1.0 and 15.5 ± 1.2 hours, respectively. Due to the clearance of drugs in the liver, the clearance rate of liver disease patients will decrease by 26-48%, and the half-life and MRT value will increase by 19-38%. Therefore, the dosing interval for liver disease patients should be extended to avoid drug accumulation.
The pharmacokinetic characteristics of oral metronidazole 20mg/kg administered 20 minutes before surgery in infants aged 1-42 weeks are consistent with those in adults.
It is a valuable therapeutic agent with a well-established role in the treatment of anaerobic bacterial and protozoal infections. Its pharmacokinetic advantages, including a longer half-life and reduced dosing frequency, enhance patient compliance and clinical outcomes. While generally well-tolerated, healthcare providers must be vigilant about potential side effects and drug interactions. Ongoing research into combination therapies, nanotechnology-based delivery systems, and extended-release formulations holds promise for expanding its clinical utility. As antimicrobial resistance evolves, it will continue to be a critical tool in the armamentarium against infectious diseases, provided it is used judiciously and in accordance with evidence-based guidelines.
Ornidazole is a 5-nitroimidazole class antibacterial drug, mainly used for treating infections caused by anaerobic bacteria, trichomonas, amoebic protozoa, etc. Its manufacturing process involves multiple steps such as raw material selection, chemical reactions, post-treatment, purification, quality control, and packaging and transportation. It is necessary to strictly follow technical specifications to ensure the purity and safety of the product.
Raw Material Selection and Pretreatment
The synthesis of Ornidazole uses 2-methyl-5-nitroimidazole and epichlorohydrin as the core raw materials. 2-Methyl-5-nitroimidazole provides the imidazole ring structure, while epichlorohydrin introduces the side chain through a ring-opening reaction. To prepare optically active products (such as S-(-)-Ornidazole or R-(+)-Ornidazole), the corresponding optically active epichlorohydrin isomers need to be used. The raw materials must undergo strict inspection to ensure purity meets the standard (typically ≥ 98%) and comply with pharmaceutical grade standards.
Chemical Reaction Process
Condensation Reaction
Dissolve 2-methyl-5-nitroimidazole in organic solvents such as ethyl acetate, add a Lewis acid catalyst (such as aluminum chloride), and then dropwise add epichlorohydrin. The reaction is carried out at low temperature (0-10℃) for 1-5 hours, generating the intermediate 1-(2,3-epoxypropyl)-2-methyl-5-nitroimidazole. This step requires controlling the temperature and reaction time to minimize the formation of by-products.
Hydrolysis Reaction
After the condensation reaction is completed, add water to the system to open the epoxide ring and hydrolyze, generating hydroxy compounds. The hydrolysis temperature is controlled at 20-30℃, and stirring for 0.5-2 hours ensures complete reaction.
Acidification and Neutralization
After filtering the hydrolyzed liquid, add the organic phase to water, then add inorganic acid (such as concentrated hydrochloric acid or 50% sulfuric acid) for acidification to reduce the pH to 0.5-2.0, promoting the transfer of the product to the aqueous phase. Subsequently, add ethyl acetate and weak base (such as ammonia water) to neutralize to a pH of 6.5-8.0, allowing the product to re-distribute to the organic phase.
Post-treatment and Purification
Drying and Concentration
After the organic phase is dried with anhydrous sodium sulfate, reduce pressure and concentrate to remove the solvent, obtaining the crude product of ornidazole. This step requires controlling the temperature and vacuum degree to avoid product decomposition.
Re-crystallization
The crude product is further purified by recrystallization. Common solvents include toluene, ethyl acetate, ethanol, or methanol, among which toluene has an appropriate solubility and is easy to volatilize, making it the preferred solvent. The recrystallization process effectively removes residual impurities and increases the product purity to over 99.5%. For optically active products, the recrystallization step is particularly important to ensure the stability of the chiral center configuration.
Quality Control and Testing
During the manufacturing process, multiple quality indicators need to be strictly monitored:
Purity testing
The analysis is conducted using high-performance liquid chromatography (HPLC) to ensure that the impurity content is below 0.5%.
Chiral purity testing
For optically active products, the enantiomeric excess (ee) value is determined using a chiral chromatographic column or an optical rotation meter to ensure compliance with standards.
Residual solvent testing
The presence of organic solvents such as ethyl acetate and toluene is detected using gas chromatography (GC) to ensure compliance with international drug registration standards (such as ICH guidelines).
Water and heavy metal testing
The moisture content is determined using the Karl Fischer method, and heavy metal residues are detected using atomic absorption spectroscopy to ensure product safety.
The purified ornidazole needs to undergo drying, grinding, sieving, and other treatments, and then be packaged according to the requirements of the dosage form. Common dosage forms include tablets, capsules, and injections, and the packaging materials must meet pharmaceutical grade standards. For example, injection solutions are packaged in non-PVC soft bags to reduce the risk of contamination. During transportation, temperature and humidity need to be controlled to prevent the product from getting damp or deteriorating.
Process Optimization and Environmental Considerations
Modern manufacturing processes emphasize the optimization of reaction conditions. For instance, a low-temperature catalytic system is employed to reduce the formation of by-products, or continuous-flow reaction technology is utilized to enhance reaction efficiency. Additionally, solvent recovery and recycling technologies are widely adopted to lower production costs and minimize environmental pollution. For example, ethyl acetate and toluene can be recovered through distillation and reused in the condensation and recrystallization steps.
Ornidazole belongs to the third generation of nitroimidazole antibiotics, which penetrate the cell membrane of pathogenic microorganisms. In anaerobic/microaerophilic environments, nitro groups are reduced to amino groups, disrupting the double stranded structure of pathogen DNA, inhibiting nucleic acid replication and transcription, and ultimately leading to microbial apoptosis; Highly selective killing of strict anaerobic bacteria, facultative anaerobic bacteria, trichomonas, amoeboids, and Giardia, with no significant toxicity to human aerobic cells.
Trichomonas vaginalis (Trichomonas vaginalis)
Trichomonas vaginalis is a sexually transmitted protozoan, with typical symptoms of vulva pruritus, foam yellow green leucorrhea, odor, urethral tingling; Traditional metronidazole has a large number of patients with gastrointestinal intolerance, while metronidazole has a prominent advantage in tolerability.
Standard adult treatment plan: single dose of 1500 mg (1.5 g); Or take 500 mg each morning and evening for 5 consecutive days; The cure rate is 94% -98%, significantly higher than the short-term regimen of tinidazole. Key clinical points:
Sexual partners must take medication simultaneously to prevent cross infection and recurrence;
The treatment course is not interrupted during menstruation, and menstrual blood does not affect drug absorption;
When combined with urinary and bladder trichomonas infections, oral systemic administration can simultaneously kill urinary tract parasites, while suppositories only act locally on the vagina and cannot cover the urethra;
Recurrent refractory trichomonas (metronidazole resistant strain): metronidazole prolongs the course of treatment to 7 days, increasing the cure rate to 91%, making it the preferred alternative drug for drug-resistant trichomonas.
Bacterial vaginosis (BV, Gardnerella+mixed anaerobic bacterial infection)
Imbalance of vaginal microbiota, reduction of lactobacilli, excessive proliferation of fragile pseudomonas, Prevotella, and Gardnerella, fishy gray white discharge, and burning sensation in the external genitalia; The combination of oral metronidazole and suppositories is a powerful curative combination:
Oral regimen: 500 mg/time, twice a day, for 7 consecutive days;
Vaginal suppository: Place 500 mg metronidazole suppository before bedtime every night for 7 consecutive days; The local drug concentration is much higher than the oral blood drug concentration, rapidly reducing the vaginal anaerobic bacterial load;
Clinical data: The recurrence rate of combination therapy is only 7.2%, while the recurrence rate of metronidazole alone is 18.6%; Bacterial vaginosis in the middle and late stages of pregnancy can easily induce premature rupture of membranes and preterm birth, and metronidazole is a safe anti infective drug in the middle and late stages of pregnancy.
Frequently Asked Questions
What is ornidazole used for?
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Is ornidazole the same as metronidazole?
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No, they are not the same drug.While both belong to the same class of antibiotics called nitroimidazoles and are used to treat similar bacterial and parasitic infections, they have different chemical structures, dosing schedules, and side-effect profiles.
What to avoid when taking ornidazole?
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Uncommon: Nausea, vomiting, diarrhoea, epigastric discomfort, dry mouth, loss of appetite.Alcohol must not be ingested when taking ornidazole or for at least 3 days after discontinuing the medicine.Ornidazole potentiates the effect of coumarin type oral anticoagulants.
What is the best time to take ornidazole?
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Take ARROW - ORNIDAZOLE during or immediately after a meal, at about the same time(s) each day.If you take ARROW - ORNIDAZOLE on an empty stomach, it may cause a stomach upset.Continue taking ARROW - ORNIDAZOLE until your doctor tells you to stop.
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