Octenidine dihydrochloride

Octenidine dihydrochloride

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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
CAS Number	70775-75-6 71251-02-00
ChEBI	CHEBI:478961
ChemSpider	46370
EC Number	274-861-8
Jmol 3D model	Interactive image
InChI InChI=1/C36H62N4.2ClH/c1-3-5-7-9-15-19-27-37-35-23-31-39(32-24-35)29-21-17-13-11-12-14-18-22-30-40-33-25-36(26-34-40)38-28-20-16-10-8-6-4-2;;/h23-26,31-34H,3-22,27-30H2,1-2H3;2*1H
SMILES Cl.Cl.N(=C1\C=C/N(/C=C1)CCCCCCCCCCN\2/C=C\C(=N\CCCCCCCC)/C=C/2)\CCCCCCCC
Properties
Chemical formula	C36H64Cl2N4
Molar mass	623.84 g·mol−1
Pharmacology
ATC code	R02AA21 combination codes: D08AJ57 G01AX66
Vapor pressure	{{{value}}}
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

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

Comparison between octenidine and chlorhexidine determined by the suspension test (exposure time 5 min.)

	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

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. Wound irrigation with octenidine caused severe complications in dogs.