Octenidine dihydrochloride

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.

Octenidine dihydrochloride[1]
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.068.035
EC Number
  • 274-861-8
UNII
  • InChI=1S/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
    Key: SMGTYJPMKXNQFY-UHFFFAOYSA-N
  • 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
  • CCCCCCCCN=C1C=CN(C=C1)CCCCCCCCCCN2C=CC(=NCCCCCCCC)C=C2.Cl.Cl
Properties
C36H64Cl2N4
Molar mass 623.84 g·mol−1
Pharmacology
R02AA21 (WHO) A01AB24 (WHO), QA01AB24 (WHO), combination codes: D08AJ57 (WHO), G01AX66 (WHO)
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Medical uses

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

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.[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

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.[6]

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]

References
  1. EC no. 274-861-8, ECHA
  2. https://www.ema.europa.eu/documents/psusa/octenidine-list-nationally-authorised-medicinal-products-psusa/00010748/202007_en.pdf
  3. 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.
  4. 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". Klinische Pädiatrie. 228 (4): 208–12. doi:10.1055/s-0042-104122. PMID 27362412. S2CID 5099338.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Sedlock D, Bailey D. Microbicidal activity of octenidine hydrochloride, a new alkanediylbis[pyridine] germicidal agent. Antimicrob Agents Chemother. 1985; 28: 786–90.
  6. Hans-P. Harke (2007), "Disinfectants", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, pp. 1–17, doi:10.1002/14356007.a08_551
  7. 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". Journal of Antimicrobial Chemotherapy. 71 (9): 2569–76. doi:10.1093/jac/dkw170. PMID 27234462.
  8. Furtwängler, Rhoikos; Laux, Carolin; Graf, Norbert; Simon, Arne (2015). "Impact of a modified Broviac maintenance care bundle on bloodstream infections in paediatric cancer patients". GMS Hygiene and Infection Control. 10: Doc15. doi:10.3205/dgkh000258. PMC 4657435. PMID 26605135.
  9. Schmidt, J.; Zyba, V.; Jung, K.; Rinke, S.; Haak, R.; Mausberg, R. F.; Ziebolz, D. (2016). "Cytotoxic effects of octenidine mouth rinse on human fibroblasts and epithelial cells – anin vitrostudy". Drug and Chemical Toxicology. 39 (3): 322–330. doi:10.3109/01480545.2015.1121274. PMID 26654138. S2CID 19546288.
  10. Kaiser, S.; Kramer, M.; Thiel, C. (2015). "Severe complications after non-intended usage of octenidine dihydrochloride. A case series with four dogs". Tierärztliche Praxis. Ausgabe K, Kleintiere/Heimtiere. 43 (5): 291–298. doi:10.15654/TPK-150029. PMID 26353826. S2CID 80926611.
  11. Lachapelle JM (2014). "A comparison of the irritant and allergenic properties of antiseptics". European Journal of Dermatology. 24 (1): 3–9. doi:10.1684/ejd.2013.2198. PMID 24492204.
  12. Franz, T.; Vögelin, E. (2012). "Aseptic tissue necrosis and chronic inflammation after irrigation of penetrating hand wounds using Octenisept®". The Journal of Hand Surgery, European Volume. 37 (1): 61–64. doi:10.1177/1753193411414353. PMID 21816890. S2CID 29175202.
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