Benzalkonium

HCID 2330

Grundinformationen

Standard-SMILES
CCCCCCCCCCCCC[N+](C)(C)Cc1ccccc1
InChIKey
VVZBFOKBSDGVGZ-UHFFFAOYSA-N
Summenformel
C22H40N+
Durchschnittliche Molmasse
318,6 g/mol

Überblick

BENZALKONIUM is an aromatic amine.

Namen und Bezeichner

Bevorzugter Name
Benzalkonium
IUPAC
benzyl-dimethyl-tridecylazanium

Namen und Synonyme

BenzalkoniumBenzalkonium ionBenzalkonium cationYouke anShieldForce AFSKeratex KHWUN Card sanitizerShieldForce AFS GelLOVE CARDRefChem:544427N6JUD5X6YBiosilk Hand and Body Lotion
Weitere Namen anzeigen
Benzalkonium Chloride Disinfectant Spraybenzyl-dimethyl-tridecylazanium47309-59-1BenzyldimethyltridecylammoniumN-Benzyl-N,N-dimethyltridecan-1-aminiumSPBio_001472Spectrum_001442Spectrum2_001566

Datenbank-Bezeichner

PubChem CID
2330
ChEMBL
CHEMBL1187417
ChEBI
CHEBI:188978
Nikkaji
J547.787E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,9
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
14
Schwere Atome
23

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 6 Einträge

D - Dermatologicals

D - Dermatologicals

R - Respiratory system

QD - Dermatologicals

QD - Dermatologicals

QR - Respiratory system

Pharmacodynamics · 1 Eintrag

Benzalkonium chloride solutions are generally categorized as biocidal agents with relative long durations of action. Their spectrum of activity has been demonstrated against bacteria, to some viruses, fungi, and protozoa, although bacterial spores are treated as being resistant to the agent. Additionally, the agent generally shows more activity against gram-positive than gram-negative bacteria. Finally, solutions of benzalkonium chloride are bacteriostatic or bactericidal based on their concentration. Bacteriostatic agents act to prevent further growth of bacterial organisms that are present while bactericidal agents function to kill bacteria that are present. In general, the activity of the agent is not largely affected by pH, but such activity does increase substantially at higher temperatures and prolonged exposure times.

Mechanism of Action · 1 Eintrag

Although not entirely elucidated, the bactericidal action of benzalkonium chloride is believed to be due to the disruption of intermolecular interactions. Such disruption can cause the dissociation of cellular membrane lipid bilayers of bacteria, resulting in compromised cellular permeability control and the leakage of important cellular contents. Additionally, other important molecular complexes like enzymes which control the maintenance of a great range of respiratory and metabolic cellular activities, are also susceptible to such deactivation. Consequently, a variety of critical intermolecular interactions and tertiary structures in very highly specific biochemical systems that allow bacterial agents to function normally can be readily disrupted or deactivated by cationic surfactants like benzalkonium chloride..

Metabolism/MetabolitesSince benzalkonium chloride is structurally a large, positively charged molecule it is likely poorly absorbed and eliminated largely in faeces, similar to other quaternary ammonium compounds.
MeSH Pharmacological Classification · 3 Einträge

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.

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.

Substances added to pharmaceutical preparations to protect them from chemical change or microbial action. They include ANTI-BACTERIAL AGENTS and antioxidants.

Absorption, Distribution and Excretion · 3 Einträge

Percutaneous absorption is considered to be insignificant. In one study, benzalkonium chloride absorption was evaluated in women using tampons containing the agent. Venous blood samples were drawn 15 minutes before the tampon application and then again at 15 min, 1 h, 3 h, and 24 h after application. Benzalkonium chloride was not detected in any of the blood samples at any time tested. Similarly, in another study, benzalkonium chloride absorption was tested in women using tampons containing the agent. Venous blood and breast milk samples were taken 15 minutes before application and 3 h and 24 h after tampon administration. Benzalkonium chloride was not found in any of the subjects' samples.. Moreover, in a study where benzalkonium chloride solution was placed on the corneal surface of rabbit subjects, at various intervals after administration, the rabbits' eyes would be washed with 1 mL saline and the following tissues and fluids were removed: bulbar and palpebral conjunctiva, aqueous humour, corneal epithelium, endothelium and stroma, iris-ciliary body, lens, vitreous, retina, and choroid. Plasma samples were obtained with direct cardiac punctures. After administration of one drop, benzalkonium chloride was found in the corneal epithelium, endothelium, and stroma, and in the bulbar and palpebral conjunctivae. Benzalkonium chloride loss from ocular tissues was such that about one-third to two thirds of its concentration (depending on the tissue) at 30 min remained after 24 hr; measurable values existed for as long as 120 hr. The administration of multiple drops led to continued accumulation of benzalkonium chloride..

Administered benzalkonium chloride is likely eliminated largely in faeces, similar to other quaternary ammonium compounds.

When applied as a topical antibacterial, antiseptic, disinfectant, or sanitizer it is believed that molecules of benzalkonium chloride are poorly absorbed (perhaps due to their large, positively charged nature), especially considering expectations for such topical applications to keep their biocidal agents available for action at the topical level and to not be absorbed significantly beyond it. When benzalkonium chloride is implemented as an excipient preservative ingredient in various eye, nose, and ear aqueous products, such products will always have other active pharmacological agents whose volume of distribution will be of greater importance. In these cases the excipients will only ever be present at the minimal levels necessary to maintain the integrity of the product substance. Moreover, Benzalkonium chloride is currently listed as a Category III ingredient by the United States Food and Drug Administration. Ingredients are listed in the FDA Category III when the data available about them are insufficient to classify as safe and effective, requiring further testing to determine more formal details about elements like human pharmacokinetic studies, and studies on the ingredients' absorption, distribution, metabolism, and excretion.

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