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Cetylpyridinium

Cetylpyridinium structure

Cetylpyridinium 

structure
  • CAS No:

    7773-52-6

  • Formula:

    C21H38N

  • Chemical Name:

    Cetylpyridinium

  • Synonyms:

    Pyridinium,1-hexadecyl-;1-Hexadecylpyridinium;Cetylpyridinium;N-Hexadecylpyridinium;Ceepryn;Hexadecylpyridinium;85040-60-4;87980-44-7;203063-55-2

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Cetylpyridinium is a pyridinium ion.|Cetylpyridinium is a quaternary ammonium with broad-spectrum antiseptic properties. Its salt form, cetylpyridinium chloride, is typically found as an active ingredient in mouthwashes, toothpastes, lozenges, throat sprays, breath sprays, and nasal sprays. In these products, it generally mediates an antiseptic activity and protective action against dental plaque and reducing gingivitis.|Cationic bactericidal surfactant used as a topical antiseptic for skin, wounds, mucous membranes, instruments, etc.; and also as a component in mouthwash and lozenges.

Cetylpyridinium Basic Attributes

304.542

304.30000

CUB7JI0JV3

DTXSID8047979

B - Blood and blood forming organs|D - Dermatologicals|R - Respiratory system

Characteristics

3.9

1.71

79-82 °C

Very soluble in water, chloroform

Toxicity

Ingestion of cetylpyridinium chloride in large doses may cause gastric upset and central nervous system depression. However, such overdose symptoms are only observed in doses 70 times greater than the concentrations of cetylpyridinium chloride found in most over-the-counter cetylpyridinium chloride products.

No readily available data regarding the protein binding of cetylpyridinium chloride is available and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent.

Drug Information

Typically employed as the cetylpyridinium chloride salt, this compound is commonly used as an active ingredient in various over-the-counter mouthwashes, toothpastes, lozenges, and mouth sprays where it is generally indicated for antiseptic actions, gingivitis and plaque prevention, as well as action or prevention against some other oropharyngeal bacterial infections.

Cetylpyridinium chloride is considered a cationic disinfectant with properties and uses similar to other such cationic surfactants. In particular, cetylpyridinium chloride has demonstrated a rapid bactericidal and fungicide effect on gram-positive pathogens and yeasts, respectively. Cetylpyridinium chloride is subsequently utilized in a variety of preparations for the local treatment of minor infections. Despite the variety of formulations in which cetylpyridinium chloride may appear as an active ingredient, it is generally accepted that it only elicits a local effect owing to the compound's relatively poor absorption by route of exposure.

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)|Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties. (See all compounds classified as Detergents.)

Most available formulations consisting of cetylpyridinium chloride as an active ingredient are either mouthwashes, tootpastes, lozenges, or mouth sprays. The oral retention of cetylpyridinium chloride given as 1 min mouth rinse of 10 mL of 2.2 MMOL solution was recorded as 65% of the administered dose. Additionally, it has been recorded that quaternary ammonium compounds like Cetylpyridinium chloride are generally poorly absorbed by the oral route. Furthermore, although systemic absorption from the parenteral route of administration is possible, systemic effects from percutaneous absorption through intact skin is considered rare.|As the quaternary ammonium compound cetylpyridinium chloride is poorly absorbed by oral route, relatively large amounts of the compound are therefore eliminated in faeces.|No readily available data regarding the volume of distribution of cetylpyridinium chloride is available and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent.|No readily available data regarding the clearance of cetylpyridinium chloride is available and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent.

No readily available data regarding the metabolism of cetylpyridinium chloride is available and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent.

No readily available data regarding the half-life of cetylpyridinium chloride is available and various products that actually contain cetylpyridinium chloride as an active ingredient suggest that no pharmacokinetic data are available for the agent.

When incorporated into mouthwashes, toothpastes, lozenges, or mouth sprays, cetylpyridinium chloride is expected to elicit a mechanism of action that decreases new dental plaque growth, decreases or removes existing dental plaque, diminishes the growth of pathogenic bacteria, and inhibits the production of virulence factors. Cetylpyridinium chloride is a quaternary ammonium compound that demonstrates a broad spectrum anti-bacterial activity. It possesses a cationic surface active agent surfactant which can absorb readily to oral surfaces. The molecules of this agent have both hydrophilic and hydrophobic groups. In action, the positively charged hydrophilic region of cetylpyridinium chloride molecules enables the compound to interact with microbial cell surfaces and even integrate into the bacterial cytoplasmic membrane. Consequently, there is a resultant disruption of bacterial membrane integrity causing a leakage of bacterial cytoplasmic components, interference with cellular metabolism, inhibition of cell growth, and ultimately - cell death. Moreover, cetylpyridinium chloride can also inhibit the synthesis of insoluble glucan by streptococcal glucosyltransferase, adsorb to pellicle-covered enamel, and inhibit co-adhesion of bacteria, and bind streptococcus mutans biofilms. This ability of cetylpyridinium chloride to be able to adsorb to pellicle covered enamel imparts substantivity to the compound molecules - that is retention in the mouth and continued antimicrobial activity for a period of time after rinsing. Taking these mechanisms into consideration, cetylpyridinium chloride may be considered an active ingredient that is effective in the treatment and prevention of bacterial or fungal disorders of the oropharyngeal cavity.

Angifonil

Computed Properties

Molecular Weight:304.5
XLogP3:8.7
Rotatable Bond Count:15
Exact Mass:304.300425216
Monoisotopic Mass:304.300425216
Topological Polar Surface Area:3.9
Heavy Atom Count:22
Formal Charge:1
Complexity:208
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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