Octenidine dihydrochloride

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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 bolaamphiphile structure, derived from pyridine, 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 neonates.

Use[edit]

Since 1987, octenidine has been used in Europe as an antiseptic, in concentrations of 0.1-2.0%.[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]

Efficacy[edit]

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[edit]

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[edit]

  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. 
  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, PMID 26353826, doi:10.15654/TPK-150029 
  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.