Octenidine dihydrochloride
Surfactant
From Wikipedia, the free encyclopedia
Octenidine dihydrochloride is a cationic surfactant, with a gemini-surfactant structure, derived from 4-aminopyridine. It is active against Gram-positive and Gram-negative bacteria. Since 1987, it has been used primarily in Europe as an antiseptic prior to medical procedures, including on neonates.
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| Names | |
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| IUPAC name
1,1′-(Decane-1,10-diyl)bis(N-octylpyridin-4(1H)-imine)—hydrogen chloride (1/2) | |
| Other names
N,N′-(decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene)bis(octylammonium) dichloride | |
| Identifiers | |
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3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.068.035 |
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| UNII |
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CompTox Dashboard (EPA) |
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| Properties | |
| C36H64Cl2N4 | |
| Molar mass | 623.84 g·mol−1 |
| Pharmacology | |
| R02AA21 (WHO) A01AB24 (WHO), QA01AB24 (WHO), combination codes: D08AJ57 (WHO), G01AX66 (WHO) | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Medical uses
Since 1987, octenidine has been used in Europe as an antiseptic, in concentrations of 0.1 to 2.0%.[citation needed] It is a substitute for chlorhexidine, with respect to its slow action and concerns about the carcinogenic impurity 4-chloroaniline.[citation needed] Octenidine preparations are less expensive than chlorhexidine and no resistance had been observed as of 2007.[3] They may contain the antiseptic phenoxyethanol.[4] It is not listed in the Annex V of authorized preservatives of the European Cosmetic Regulation 1223/2009.
Efficacy
Octenidine dihydrochloride is active against Gram-positive and Gram-negative bacteria.[5]
In vitro suspension tests with 5 minute exposure time have shown that octenidine requires lower effective concentrations than chlorhexidine to kill common bacteria like Staphylococcus aureus, Escherichia coli, Proteus mirabilis and the yeast Candida albicans.[6]
| Effective concentration, % | ||
|---|---|---|
| Octenidine dihydrochloride | Chlorhexidine digluconate | |
| Staphylococcus aureus | 0.025 | >0.2 |
| Escherichia coli | 0.025 | 0.1 |
| Proteus mirabilis | 0.025 | >0.2 |
| Candida albicans | 0.01 | 0.025 |
| Pseudomonas aeruginosa | 0.025 | >0.2 |
An observational study of using octenidine on the skin of patients in 17 intensive care units in Berlin in 2014 showed decreasing nosocomial infection rates.[7]
In a survey of German neonatal intensive-care units octenidine without phenoxyethanol and octenidine were the most common skin antiseptics used for intensive-care procedures. Skin complications included blistering, necrosis and scarring, which has not been previously reported in this population.[4]
In a 2016 study of pediatric cancer patients with long-term central venous access devices using octenidine/isopropanol for the disinfection of catheter hubs and 3-way stopcocks as part of a bundled intervention, the risk of bloodstream infections decreased.[8]
Safety
In a 2016 in vitro study of mouth rinses on gingival fibroblasts and epithelial cells octenidine showed a less cytotoxic effect, especially on epithelial cells, compared to chlorhexidine after 15 min.[9] Wound irrigation with octenidine has caused severe complications in dogs,[10] aseptic necrosis and chronic inflammation in penetrating hand wounds in humans.[11][12]
Synthesis
The secondary amine (3) is formed by reaction of octan-1-amine (1) and 4-bromopyridine (2). Treatment of this with 1,10-dichlorodecane (4) yields octenidine as its dihydrochloride salt.[13][14][15]