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
70775-75-6
71251-02-00
ChEBI CHEBI:478961
ChemSpider 46370
EC Number 274-861-8
Jmol 3D model Interactive image
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. It is primarily used as an antiseptic

Use[edit]

Since 1987, octenidine is being used in Europe as an antiseptic, in concentrations of 0.1-2.0%. It is a substitute for chlorhexidine, with respect to its slow action and concerns about the carcinogenic impurity 4-chloroaniline. Octenidine antiseptics often contain phenoxyethanol.

Efficacy[edit]

Comparison between octenidine and chlorhexidine determined by the suspension test (exposure time 5 min.)[2]
  Effective concentration, %
Octenidine dihydrochloride Chlorhexidine digluconate
Staphylococcus aureus 0.025 >0.2
Escherichia coli 0.025 0.1
Proteus mirabilis 0.025 >0.2
Pseudomonas aeruginosa 0.025 >0.2
Candida albicans 0.01 0.025

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.[2] Wound irrigation with octenidine caused severe complications in dogs.[3]

References[edit]

  1. ^ 274-861-8, European Chemical Substances Information System
  2. ^ 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 
  3. ^ 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