chemical structure of benzalkonium chloride

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Benzalkonium chloride

Benzalkonium Chloride is an organic compound that is used as an antiseptic and spermicide. This product is a nitrogenous cationic surface-acting agent belonging to the quaternary ammonium group. Benzalkonium chloride is a mixture of alkylbenzyl dimethylammonium chlorides of various alkyl chain lengths. The greatest bactericidal activity is associated with the C12-C14 alkyl derivatives. more...

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It is one of the safest synthetic biocides known, and has a long history of efficacious use. Applications are extremely wide ranging, from disinfectant formulations to microbial corrosion inhibition in the oilfield sector. It is deemed safe for human use, and is widely used in eyewashes, hand and face washes, mouthwashes, spermicidal creams, and in various other cleaners, sanitizers, and disinfectants.

Benzalkonium chloride is readily soluble in water, alcohol, and acetone. Formulation requires great care as Benzalkonium can be inactivated by certain organic compounds, including soap, and must not be mixed with anionic surfactants. Hard water salts can also reduce biocidal activity. Although newer formulations are more resistant to deactivation, as with any disinfectant, it is recommended that surfaces are rinsed well before disinfection.

Aqueous solutions of benzalkonium chloride are neutral to slightly alkaline, colorless, and nonstaining. Solutions foam profusely when shaken, have a bitter taste, and a faint almond-like odour, which is only detectable in concentrated solutions.

The mechanism of bactericidal/microbicidal action is thought to be due to disruption of intermolecular interactions. This can cause dissociation of cellular membrane bilayers, which compromises cellular permeability controls and induces leakage of cellular contents. Other biomolecular complexes within the bacterial cell can also undergo dissociation. Enzymes, which finely control a plethora of respiratory and metabolic cellular activities, are particularly susceptible to deactivation. Critical intermolecular interactions and tertiary structures in such highly specific biochemical systems can be readily disrupted by cationic surfactants.

Benzalkonium chloride solutions are rapidly acting anti-infective agents with a moderately long duration of action. They are active against bacteria and some viruses, fungi, and protozoa. Bacterial spores are considered to be resistant. Solutions are bacteriostatic or bactericidal according to their concentration. Gram-positive bacteria are generally more susceptible than gram-negative. Activity is not greatly affected by pH, but increases substantially at higher temperatures and prolonged exposure times.

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Benzalkonium Chloride 0.1% Topical Gel
From International Journal of Pharmaceutical Compounding, 9/1/04

METHOD OF PREPARATION

1. Calculate the required quantity of each ingredient for the total amount to be prepared.

2. Accurately weigh and/or measure each ingredient.

3. Disperse the carbomer slowly by sprinkling onto about 95 mL of rapidly agitated purified water.

4. Decrease the agitation to slow mixing; add the benzalkonium chloride and mix well.

5. Add sufficient trolatnine to obtain a pH of approximately 6.

6. Add sufficient purified water to volume and mix well.

7. Package and label.

PACKAGING

Package in tight, light-resistant containers.1

LABELING

Keep out of reach of children. Use only as directed.

STABILITY

A beyond-use date of up to 6 months would be appropriate for this preparation.1

USE

Benzalkonium topical gel has been used as a topical antiseptic for the skin.

QUALITY CONTROL

Quality-control assessment can include theoretical weight compared to actual weight, pH, specific gravity, active drug assay, color, clarity, texture-surface, texture-spatula spread, appearance, feel, rheological properties and physical observations.2

DISCUSSION

Benzalkonium chloride topical gel can be used in the treatment of superficial minor skin infections and as a skin disinfectant gel, especially for individuals that may be allergic to ingredients contained in commercially available skin disinfectant products.

Benzalkonium chloride is a bactericidal antimicrobial agent commonly used as a preservative in many ophthalmic, otic, nasal and parenteral formulations. It occurs as a white or yellowish-white amorphous powder, a thick gel or gelatinous pieces/flakes with a characteristic mild, aromatic odor, soapy touch and very bitter taste. It is very soluble in water, alcohol and acetone. It is hygroscopic and a 10% w/v aqueous solution has a pH in the range of 5 to 8. Benzalkonium Chloride Solution NF is a clear liquid, colorless or slightly yellow unless a color has been added. It has an aromatic odor and a bitter taste. Benzalkonium chloride is composed of a mixture of straight chain homologs that possess different physical, chemical and microbiological properties. The proportions of these homologs in the mixture determine its effectiveness as a preservative and disinfectant.3

Carbopol 934P (a carbomer) is a synthetic, high-molecular-weight polymer composed of acrylic acid cross-linked with either allyl sucrose or allyl ethers of pentaerythritol. Carbomers occur as white-colored, fluffy, acidic, hygroscopic powders with a slight characteristic odor. The molecular weight of carbomer 934 is approximately 3 × 10^sup 6^. The pH of a 0.5-1.0% dispersion is in the range of 2.5 to 3.5. Carbomers are soluble in water and, after neutralization, in 95% ethanol and glycerin. When dispersed in water, an acidic colloidal solution of low viscosity will form that will thicken when an alkaline material, such as triethanolamine, is added. Effort should be made to minimize the incorporation of air bubbles into the gel. Maximum viscosity can generally be obtained in a pH range of 6 to 11.4

Trolamine (C^sub 6^H^sub 15^NO^sub 3^, MW 149.19, TEA, triethanolamine) is an alkalizing and emulsifying agent. It occurs as a variable mixture of alkanolamines and is a clear, colorless to pale yellow-colored viscous liquid with a slight ammoniacal odor. Its specific gravity is about 1.120-1.128 g/mL and it has a pH of 10.5 in a 0.1 N aqueous solution. It is very hygroscopic; it is miscible with water, 95% ethanol, methanol and acetone.5

Purified water is water that is obtained by distillation, ion exchange, reverse osmosis or some other suitable process. It is a clear, colorless, odorless and tasteless liquid. It is miscible with most polar solvents and is chemically stable in all physical states (ice, liquid and steam).6

REFERENCES

1. US Pharmacopeial Convention, Inc. United States Pharmacopeia 27-National Formulary 22. Rockville, MD: US Pharmacopeial Convention, Inc.; 2004: 2345-2349.

2. Allen LV Jr. Standard operating procedure for performing physical quality assessment of ointments/creams/gels. IJPC 1998; 2: 308-309.

3. Kibbe AH. Benzalkonium chloride. In: Rowe RC, Sheskey PJ, Weller PJ, eds. Handbook of Pharmaceutical Excipients. 4th ed. Washington, DC: American Pharmaceutical Association; 2003: 45-47.

4. Koleng JJ, McGinity JW, Wilber WR. Carbomer. In: Rowe RC, Sheskey PJ, Weller PJ, eds. Handbook of Pharmaceutical Excipients. 4th ed. Washington, DC: American Pharmaceutical Association; 2003: 89-92.

5. Goskonda SR, Lee JC. Triethanolamine. In: Rowe RC, Sheskey PJ, Weller PJ, eds. Handbook of Pharmaceutical Excipients. 4th ed. Washington, DC: American Pharmaceutical Association; 2003: 663-664.

6. Ellison A, Nash RA, Wilkin MJ. Water. In: Rowe RC, Sheskey PJ, Weller PJ, eds. Handbook of Pharmaceutical Excipients. 4th ed. Washington, DC: American Pharmaceutical Association; 2003: 672-676.

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