Cetalkonium chloride (CKC) is a

quaternary ammonium In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations ...

compound of the alkyl-benzyldimethylammonium chloride family, the alkyl group having a chain length of C16 (16 carbons). It is used in pharmaceutical products either as an

excipient An excipient is a substance formulated alongside the active ingredient of a medication, included for the purpose of long-term stabilization, bulking up solid formulations that contain potent active ingredients in small amounts (thus often referred ...

(Cationorm, Retaine MGD) or as an active ingredient (

Bonjela Bonjela is a brand of oral treatments intended to relieve the pain of mouth ulcers and denture sores. The brand covers a range of products. Bonjela Adult and Cool are oral gels containing keratolytic and mildly antiseptic salicylic acid in the fo ...

, Pansoral). It may be found in very small amount in the excipient

benzalkonium chloride Benzalkonium chloride (BZK, BKC, BAK, BAC), also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs hav ...

mixture (typically less than 5% of the total mixture). Cetalkonium chloride is purchased as a raw material in dry form as a white powder.

Applications

Cetalkonium chloride can be used in different applications depending on its concentration.

Anti-infective agent

It can be used as an active ingredient to relieve the pain of

mouth ulcer A mouth ulcer (aphtha) is an ulcer that occurs on the mucous membrane of the oral cavity. Mouth ulcers are very common, occurring in association with many diseases and by many different mechanisms, but usually there is no serious underlying cause ...

s and denture sores in buccal solutions or gels such as Pansoral or in

. The usual concentration in these products is 0.01% (w/w). However, it isn't known as a potent bactericidal compound, mainly because of its low solubility in water. For example, US and European pharmacopeias enforce suppliers of

to limit the amount of cetalkonium chloride in the mixture to less than 5% w/w.

Cationic surface-active agent

Cetalkonium chloride can also be used as a pharmaceutical

due to its

amphiphilic An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compoun ...

property and cationic charge. For example, it has recently been included in a contact lens to bind an anionic active drug to serve as reservoir and extend the release rate of the molecule. Most frequently, it is used as an

emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Altho ...

and cationic agent in ophthalmic nanoemulsions in products like Cationorm and Retaine MGD. Due to its high

lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...

, cetalkonium chloride is strongly associated to oil nanodroplets at the oil/water interface in oil-in-water emulsions, hence providing a positive charge at the surface of the oil nanodroplets. This polarization of the nanodroplets stabilizes the emulsion by creating an electrostatic repulsion between the nanodroplets and is the driving force behind the biological adhesion of the nanodroplets to negatively charged cell epithelium ''

in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...

''. In life science the cationic charge of cetalkonium is used to separate biological extracts according to their charge.

Biological activity

Biological activity In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ...

of cetalkonium chloride as

has been widely described in the scientific literature. Cetalkonium chloride acts by creating a positive charge that provides bioadhesive properties of the cationic nanoemulsions on the negatively charged ocular surface. Hence, increasing the penetration of active ingredients formulated in cationic nanoemulsions into ocular tissues. Even more, cetalkonium chloride cationic emulsions seem to improve healing of corneal lesions.

Safety

Even though cetalkonium chloride belongs to the family of

, the ophthalmic use of cetalkonium chloride cationic nanoemulsions have been shown to be safe. These observations are explained by the fact that cetalkonium chloride present in oil-in-water emulsions is bound to the oil nanodroplets therefore sequestered from the water phase and not available to cause damages to ocular tissues. Pansoral has been on the market since 1981 and Cationorm since 2008, both products being well accepted by patients.

Regulatory

Cetalkonium is listed on the FDA OTC ingredient list updated April 2010. The MHRA has published in 2012 the "Consolidated list of substances which are present in authorized medicines for general sale" in which CKC is cited. The highest authorized concentration is 0.1% when administered topically and in the mouth.

References

External links

*{{Commons category-inline Quaternary ammonium compounds Chlorides Antiseptics Cationic surfactants