Chlorhexidine diacetate is a commonly used antibacterial drug, which belongs to the class of benzamide antibacterial agents. The chemical formula is C26H38Cl2N10O4, which is white or off-white crystalline powder. Its form can change under different conditions, but it is usually relatively fine crystals or small particles. It can be slowly dissolved in water with a solubility of 4.15mg/mL, but heating is required. It also has good solubility in methanol and ethanol, and can be used to prepare its mouthwash. It is almost insoluble in chloroform, ether and benzene. As a compound widely used in medical and personal care products, the exploration and research of its physical properties are always a topic of constant concern. An in-depth understanding of its related properties will not only help the precision of pharmaceutical preparations and applications, but also Lay the foundation for a better understanding of the mechanism of drug action.
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Chemical Formula |
C26H38Cl2N10O4 |
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Exact Mass |
624 |
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Molecular Weight |
625 |
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m/z |
624 (100.0%), 626 (63.9%), 625 (28.1%), 627 (18.0%), 628 (10.2%), 626 (3.8%), 625 (3.7%), 629 (2.9%), 628 (2.4%), 627 (2.4%), 626 (1.0%) |
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Elemental Analysis |
C, 49.92; H, 6.12; Cl, 11.33; N, 22.39; O, 10.23 |
Chlorhexidine Diacetate, also known as diacetyl chlorhexidine, is an oral antibacterial drug widely used in the field of surgery and oral hygiene. It has broad-spectrum antibacterial ability and can kill a variety of pathogenic microorganisms, including bacteria, fungi and viruses.
In the medical field, the sterilization of surgical operations is one of the most basic practices. it can be used for disinfection of operating room surfaces, surgical instruments and medical instruments, etc. It can effectively kill pathogens and reduce the risk of surgical infection. In addition, it can be used to clean the skin and mucous membranes of the surgical site, thereby reducing the risk of postoperative infection.
It has a wide range of applications in the field of oral hygiene. It can be used to treat diseases such as periodontitis, canker sores and bad breath, and promote oral health. In addition, it is also commonly used in antibacterial treatment before and after oral surgery to prevent postoperative infection.
It can be used to disinfect skin lesions such as wounds, burns, wounds and acne, and eliminate bacterial infections. In addition, it can be used to temporarily relieve symptoms such as itching and irritation of the skin and improve the condition of the skin.
It can also be used in animal health, treatment and prevention. For example, in the field of veterinary medicine, it is widely used in the sterilization and disinfection of livestock to prevent and control the occurrence of poultry and livestock epidemics.
In addition to the above applications, it can also be used to prepare some drugs. For example, it is used as an ingredient in the formulation of pharmaceuticals to treat ailments such as oral infections, folliculitis, urinary tract infections and fungal skin infections.
Chlorhexidine acetate can interfere with the synthesis of cell membranes and affect their metabolic processes, causing denaturation of bacterial proteins and exerting bactericidal effects. It is suitable for disinfecting small and superficial skin, and can kill various pathogens such as Staphylococcus aureus, Escherichia coli, and Candida albicans, effectively preventing and controlling skin infections.
Chlorhexidine acetate can directly act on the cytoplasmic membrane of microorganisms, causing changes in their permeability, leading to the leakage of cell contents and death, thereby playing a disinfection role. In the medical field, chlorhexidine acetate is commonly used for disinfection of surgical instruments, syringes, catheters, and other medical devices to ensure their sterility and reduce the occurrence of hospital infections.
Chlorhexidine acetate has broad-spectrum antibacterial activity and can effectively kill various pathogens at the wound site, including Staphylococcus, Streptococcus, and anaerobic bacteria. In trauma treatment, chlorhexidine acetate can be directly applied to fresh wounds, exerting a disinfectant effect, helping to promote wound healing and reduce the risk of infection.
Chlorhexidine acetate can not only kill bacteria, but also interfere with the synthesis of cell walls, causing rapid cell rupture and dissolution. At the same time, it can also interfere with protein synthesis, causing bacterial death. This makes chlorhexidine acetate have unique advantages in the treatment of certain bacterial infectious diseases. For example, in the adjuvant treatment of oral infections, skin infections, and other diseases, chlorhexidine acetate can play a good antibacterial role and accelerate the recovery of the disease.
Chlorhexidine Diacetate is a disinfectant widely used in healthcare, especially for hand and surface disinfection. It has broad-spectrum antibacterial activity and can effectively kill a variety of microorganisms such as bacteria, viruses and fungi.
The synthetic route of product:
Concrete synthetic route is as follows:
1. Preparation of 5-chloro-2-methoxyphenylacetate
5-Chloro-2-methoxyphenylacetate is the precursor compound of product, and its preparation method is as follows:
(1)
Take benzaldehyde and 5-chloro-2-methoxyphenylacetic acid, add it to sodium hydroxide solution, and reflux at 110°C for 3 hours to obtain 5-chloro-2-(benzoyloxy)phenylacetic acid .
(2)
Condensing 5-chloro-2-(benzoyloxy)phenylacetic acid and formyl chloride to obtain 5-chloro-2-(benzoyloxy)phenylacetic acid methyl ester.
(3)
Hydrolyzing methyl 5-chloro-2-(benzoyloxy)phenylacetate to obtain 5-chloro-2-methoxyphenylacetate.
2. Preparation of nucleosides:
Nucleosides are intermediates synthesized from Chlorhexidine Diacetate. According to literature reports, nucleosides obtained by different methods are different. Here's one of those methods:
(1)
Take 5-chloro-2-methoxyphenylacetic acid ester and excess ammonium sulfate, add them to sulfuric acid solution, and react at 85°C for 30min to obtain 4-amino-5-chloro-2-methoxyphenylacetic acid.
(2)
Then take nitric acid and 4-amino-5-chloro-2-methoxyphenylacetic acid for nitration reaction at 25°C for 1h. The resulting product was reacted with copper acetate solution to give 4-chloro-N,N'-bis(2-hydroxyethyl)benzamide.
(3)
Finally, 4-chloro-N,N'-bis(2-hydroxyethyl)benzamide and ammonium chloride were reacted in ethanol to obtain nucleosides.
The reaction mechanism of product:
The synthesis of it involves multiple reactions, and each reaction has its specific reaction mechanism.
1. Nitrification reaction:
The nitration reaction is to nitrate 4-amino-5-chloro-2-methoxyphenylacetic acid, and the reaction mechanism is as follows:
(1)
Nitric acid reacts with ammonium sulfate to produce nitric acid and sulfuric acid.
(2)
Nicotinic acid reacts with 4-amino-5-chloro-2-methoxyphenylacetic acid, a nucleophilic substitution reaction occurs, and a nitro group replaces a methoxy group to generate 4-amino-5-chloro-2-nitrobenzene acetic acid.
(3)
In the presence of copper acetate, 4-amino-5-chloro-2-nitrophenylacetic acid reacts with sodium hydroxide to undergo aromatic tautomerization to generate 4-chloro-N,N'-bis( 2-Hydroxyethyl) benzamide.
It should be noted here that the entire nitrification reaction needs to be carried out under relatively protected conditions to avoid side reactions or danger.
2. Nucleoside generation reaction:
The formation reaction of nucleoside is as follows:
Add 4-chloro-N,N'-bis(2-hydroxyethyl)benzamide and ammonium chloride together to ethanol, a nucleophilic substitution reaction occurs, and the chloride ion replaces one of the dihydroxyl groups, This produces N,N'-bis(2-hydroxyethyl)4,5-dichlorobenzamide.
The obtained N,N'-bis(2-hydroxyethyl)4,5-dichlorobenzamide reacts with sodium bisulfite to generate nucleosides.
Application Status
Widely recognized and used
Chlorhexidine acetate is widely recognized for its application in the medical field. Its broad-spectrum antimicrobial properties and low toxicity make it one of the preferred disinfectants in many medical institutions.
Continuous Research and Improvement
Although chlorhexidine acetate already has a wide application base, scholars are still exploring its new application scenarios and improvement methods.
Concerns about potential risks
Although chlorhexidine acetate has fewer toxic side effects, its long-term use or improper use may still pose some potential risks. Therefore, when using chlorhexidine acetate, it is necessary to follow the instructions or medical advice strictly to avoid overdose or improper use.
For example, there are studies on combining Chlorhexidine Acetate with other antibacterial drugs in the hope of obtaining better antibacterial effects; and there are also studies on the stability and effectiveness of Chlorhexidine Acetate in specific environments to ensure its reliability in practical applications.
The stability and effectiveness of chlorhexidine acetate in specific environments varies depending on the specific conditions.
Stability
0.05% Chlorhexidine acetate solution: it has been found that the classical thermostatic accelerated method was used to predict the expiration date of 0.05% Chlorhexidine acetate solution, and the expiration date (t0.9) at room temperature 25°C was 3.62 years. This indicates that under proper storage conditions, chlorhexidine acetate solution at this concentration has good chemical stability.
Effectiveness
- Antimicrobial and disinfectant effect: Chlorhexidine acetate is a broad-spectrum antimicrobial agent with strong bactericidal effect on gram-positive and negative bacteria and fungi, and is also effective against Pseudomonas aeruginosa. It is commonly used for disinfecting skin, flushing wounds, and sterilizing surgical instruments. For example, hand disinfection using Chlorhexidine Acetate solution is effective in killing a wide range of bacteria and viruses, including influenza virus and Staphylococcus aureus.
- Preservative effect: Chlorhexidine acetate can also be used as an effective preservative to extend the shelf life of food and pharmaceuticals. One study found that adding chlorhexidine acetate solution to fruit juices inhibited the growth of bacteria and molds, thereby extending the freshness of the juice.
Changes in effectiveness in specific environments
Variation in concentration: The effectiveness of chlorhexidine acetate is closely related to its concentration. Concentrations that are too low may result in poor bactericidal effects, while concentrations that are too high may increase skin irritation. Therefore, it is necessary to strictly control the concentration when using it.
PH: Chlorhexidine acetate solution is weakly acidic and alkaline, with a pH generally between 6 and 7. Its stability and effectiveness may be affected in specific environments, such as those that are too acidic or alkaline.
Temperature: High temperatures may cause chlorhexidine acetate to decompose and reduce its effectiveness. Therefore, high temperature environments need to be avoided during storage and use.
Light: Prolonged exposure to light may also have an effect on the stability of chlorhexidine acetate. Therefore, direct sunlight should be avoided during storage.
Chlorhexidine diacetate remains a vital tool in infection control, with applications spanning human and veterinary medicine, industry, and environmental health. Its broad-spectrum activity, residual efficacy, and versatility ensure its continued relevance in an era of rising antimicrobial resistance. However, safety concerns and environmental impacts necessitate judicious use and sustainable practices. As research advances, innovations in drug delivery, combination therapies, and green synthesis will further optimize CHD's role in safeguarding public health. By balancing efficacy with responsibility, CHD can continue to protect lives and livelihoods for decades to come.
In summary, the stability and effectiveness of chlorhexidine acetate in a given environment is affected by a number of factors. To ensure its optimal effectiveness, it needs to be fully evaluated and tested prior to use, and the relevant requirements should be strictly adhered to during storage and use.
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