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Octenidine dihydrochloride

Octenidine dihydrochloride[1]
Octenidine dihydrochloride.png
Names
IUPAC name
N-octyl-1-[10-(4-octyliminopyridin-1-yl)decyl]pyridin-4-imine dihydrochloride
Systematic IUPAC name
N,N'-(decane-1,10-diyldipyridin-1-yl-4-ylidene)dioctan-1-amine dihydrochloride
Other names
N,N'-(decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene)bis(octylammonium) dichloride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.068.035
EC Number 274-861-8
Properties
C36H64Cl2N4
Molar mass 623.84 g·mol−1
Pharmacology
R02AA21 (WHO) combination codes: D08AJ57 (WHO) G01AX66 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Octenidine dihydrochloride is a cationic surfactant, with a gemini-surfactant structure, derived from pyridine. 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.

Use

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.[2] They may contain the antiseptic phenoxyethanol.[3] 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.[4]

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.[5]

Comparison between octenidine and chlorhexidine determined by the suspension test after 5 minutes of exposure.
  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.[6]

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.[3]

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.[7]

Safety

Octenidine is absorbed neither through the skin, nor through mucous membranes, nor via wounds and does not pass the placental barrier. However, cation-active compounds cause local irritation and are extremely poisonous when administered parenterally.[5]

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.[8] Wound irrigation with octenidine has caused severe complications in dogs,[9] aseptic necrosis and chronic inflammation in penetrating hand wounds.[10]

References

  1. ^ EC no. 274-861-8, ECHA
  2. ^ Al-Doori Z, Goroncy-Bermes P, Gemmell C et al. Low-level exposure of MRSA to octenidine dihydrochloride does not select for resistance. J Antimicrob Chemother 2007; 59: 1280–1.
  3. ^ a b Biermann CD1, Kribs A1, Roth B1, Tantcheva-Poor I2. (2016). "Use and Cutaneous Side Effects of Skin Antiseptics in Extremely Low Birth Weight Infants - A Retrospective Survey of the German NICUs". Klin Padiatr. 228 (4): 208–12. doi:10.1055/s-0042-104122.CS1 maint: multiple names: authors list (link)
  4. ^ Sedlock D, Bailey D. Microbicidal activity of octenidine hydrochloride, a new alkanediylbis[pyridine] germicidal agent. Antimicrob Agents Chemother. 1985; 28: 786–90.
  5. ^ a b Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551
  6. ^ Gastmeier P, Kämpf K, Behnke M, Geffers C, Schwab F (2016). "An observational study of the universal use of octenidine to decrease nosocomial bloodstream infections and MDR organisms". J Antimicrob Chemother. 71 (9): 2569–76. doi:10.1093/jac/dkw170.
  7. ^ Furtwängler R, Laux C, Graf N, Simon A. Impact of a modified Broviac maintenance care bundle on bloodstream infections in paediatric cancer patients. GMS Hyg Infect Control. 2015 Nov 16;10:Doc15. doi: 10.3205/dgkh000258.
  8. ^ Schmidt J, Zyba V, Jung K, Rinke S, Haak R, Mausberg RF, Ziebolz D. Cytotoxic effects of octenidine mouth rinse on human fibroblasts and epithelial cells - an in vitro study. Drug Chem Toxicol. 2016;39(3):322-30. doi: 10.3109/01480545.2015.1121274.
  9. ^ Kaiser, S.; Kramer, M.; Thiel, C. (2015), "Severe complications after non-intended usage of octenidine dihydrochloride. A case series with four dogs.", Tierärztliche Praxis. Ausg. K, Kleintiere/Heimtiere, 43 (5): 291–298, doi:10.15654/TPK-150029, PMID 26353826
  10. ^ Lachapelle JM (2014). "A comparison of the irritant and allergenic properties of antiseptics". Eur J Dermatol. 24 (1): 3–9. doi:10.1684/ejd.2013.2198.