N-Decyl-N,N-dimethyldecan-1-aminium chloride, also known as Diecyldimethylammonium chloride, or DDAC, is a broad-spectrum biocide that has antimicrobial activity against a variety of pathogens, including both enveloped and non-enveloped viruses, Pseudomonas aeruginosa, Legionella pneumophilia, Staphylococcus aureus, and Escherichia coli[1].

Absorption, Distribution and Excretion
DDAC (40% aqueous solution, available in both radiolabeled (14C) and non-radiolabeled forms) was used to determine the exact pharmacokinetics of its absorption, distribution, and excretion. It was administered by gavage to Charles River CD rats (Crl CD(SD)Br – 5 rats/sex/group) using three dosage regimens: 1) a single low dose (5 mg/kg); 2) repeated low doses of 34 ppm "cold" added to the diet daily for 14 days, followed by administration of 5 mg/kg of [14C]-DDCA (9.01 mCi/mmol, radiochemical purity 99%); or 3) a single high dose of 50 mg/kg. The radioactive material was primarily excreted in feces (89-99%), with a small amount excreted in urine (<2.5%), and only a very small amount exhaled. Highly ionic DDAC is poorly absorbed by the gastrointestinal tract…

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Metabolism/Metabolites
DDAC (40% aqueous solution, including radiolabeled (¹⁴C) and non-radiolabeled forms) was used in a definitive pharmacokinetic study to determine its absorption, distribution, and excretion. The drug was administered orally via gavage to Charles River CD (Crl CD(SD)Br--5/sex/group)… In the appendix, the metabolomic profile was determined through a two-step experiment. First, another group of rats (10 male Charles River CD (Crl CD(SD)Br)) were treated with 50 mg/kg of (14C)-DDAC to obtain sufficient (14C) residues for use as standards. The (14C) metabolites were characterized using thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), and mass spectrometry (MS). The second part of the experiment involved analyzing the metabolites in fecal samples obtained in the initial study using a “standard” metabolomic profile. The results showed that the metabolism was sex-specific. Females metabolized the parent compound more efficiently than males. The metabolic process likely involved microorganisms and the oxidation of two decyl side chains, generating hydroxyl and hydroxyketone derivatives. No modification with methyl substituents was observed.

Toxicity Summary
Identification and Uses: Didecyl dimethyl ammonium chloride is a clear, yellow liquid with an ethanol odor. It is used as an algaecide, bactericide, fungicide, bacteriostatic agent, viricide, tuberculosis inhibitor, molluscicide, disinfectant, wood preservative, deodorant, and insecticide. It has been used in combination with prednisolone to treat patients with impetigo-like eczema. Human Exposure and Toxicity: The main systemic adverse reactions reported are nausea, headache, and sore throat. The main skin adverse reactions reported are rash, burning sensation, numbness, and pruritus. There have been case reports of dermatitis caused by detergents/disinfectants. A 24-year-old woman who had worked in a hospital for 2 years presented with dermatitis on the back of her wrists for 2 months. Patch tests showed a positive reaction to didecyl dimethyl ammonium chloride and bis(aminopropyl)lauramide, both commonly found in detergents/disinfectants. According to the U.S. Environmental Protection Agency (EPA) classification, dialcyldimethylammonium chloride is unlikely to be carcinogenic to humans. Animal studies: In animals, dialcyldimethylammonium chloride is a serious eye and skin irritant, but not a sensitizing agent. In rodents, dialcyldimethylammonium chloride exhibits moderate acute oral toxicity and may have effects on the liver and central nervous system. In rats, no carcinogenic effects were observed, but at a concentration of 1500 ppm, both male and female rats developed treatment-related mesenteric lymph node lesions (congestive sinusoids, hemosiderinosis, and histiocytosis) and bile duct hyperplasia. No developmental effects were observed in rats. In rabbit developmental studies, an increase in stillbirths and decreased fetal weight were observed in the 10.0 mg/kg dose group. In the Ames assay, dialcyldimethylammonium chloride was not mutagenic to the tested strains of Salmonella Typhimurium, regardless of microsomal activation (S-9 fraction). In rats and Chinese hamster ovary cells, dialc-dimethylammonium chloride (DDAC) was non-mutagenic and did not induce unplanned DNA synthesis. Ecotoxicity studies: Swimming ability of juvenile rainbow trout was significantly reduced. Significantly reduced larval growth and survival were observed at all tested concentrations and in all sturgeon age groups. The larval stage was generally more sensitive than the fry stage. Acute toxicity tests on fertilized eggs were unsuccessful. Developmental stage altered the sensitivity of coho salmon to Bardac 2280, with larvae being approximately twice as sensitive as juveniles.

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Toxicity Data
LC50 (rat) = 70 mg/m3Interactions
The bactericidal activity of the quaternary ammonium salt dialc-dimethylammonium chloride (DDAC) was inhibited by the soap sodium lauryl laurate (NaLA): the minimum lethal concentration (MLC) of DDAC against Staphylococcus aureus was 63 μg/mL in the absence of NaLA and 250 μg/mL in the presence of 0.01% NaLA. The relationship between the neutralization effect and the mechanism of action of DDAC was investigated. Compared to the absence of NaLA, the apparent uptake of DDAC by cells was not inhibited by NaLA. The NaLA solution was alkaline at pH, but DDAC exhibited higher bactericidal activity at pH 11 than at pH 7. Although the presence of NaLA did not significantly affect the effect of DDAC on increasing the turbidity of cell suspensions, the mixture of these reagents (without cells) itself exhibited some turbidity. Based on these findings, it is inferred that NaLA can form less reactive complexes with DDAC through ionic and hydrophobic interactions…
Non-human toxicity values

Oral LD50 in rats: 84 mg/kg
Oral LD50 in male rats: 331 mg/kg /65% ai/ /from table/
Oral LD50 in female rats: 238 mg/kg /65% ai/ /from table/
Oral LD50 in rats: 238 mg/kg /80% ai/
For more complete non-human toxicity data on dialcyldimethylammonium chloride (out of 10), please visit the HSDB record page.

[1]. Anderson SE, et al. Evaluation of the irritancy and hypersensitivity potential following topical application of didecyldimethylammonium chloride. J Immunotoxicol. 2016;13(4):557-566.

Didecyldimethylammonium chloride is an organic molecular entity. See also: Didecyldimethylammonium (containing the active moiety); benzalkonium chloride; Didecyldimethylammonium chloride (ingredient); chlorhexidine gluconate; Didecyldimethylammonium chloride (ingredient)... See more...

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Therapeutic Uses
EXPL THER describes a double-blind trial in which two concentrations of Didecyldimethylammonium chloride (Hoe S-2922, Bardac-22) were used in combination with prednisolone to treat eczema in 30 hospitalized impetigo patients. The study found no significant difference in efficacy, but the higher concentration group showed slightly better efficacy.

C22H48CLN

362.08

361.347

7173-51-5

20256-56-8 (Parent)

23558

Colorless crystals
Clear yellow liquid /commercial aqueous solution/
Solid powder of slight yellowish color at 20 °C

0.95 g/cm3 (20ºC)

>180°C

94-100°C

4.348

0

1

18

24

200

0

[Cl-].[N+](C([H])([H])[H])(C([H])([H])[H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

RUPBZQFQVRMKDG-UHFFFAOYSA-M

InChI=1S/C22H48N.ClH/c1-5-7-9-11-13-15-17-19-21-23(3,4)22-20-18-16-14-12-10-8-6-2;/h5-22H2,1-4H3;1H/q+1;/p-1

didecyl(dimethyl)azanium;chloride

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : 100 mg/mL (276.18 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)