Octenidine dihydrochloride

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Structural formula
Structural formula of octenidine dihydrochloride
General
Non-proprietary name Octenidine
other names
  • N -Octyl-1- [10- (4-octyliminopyridin-1-yl) decyl] pyridin-4-imine ( IUPAC )
  • N , N '- (Decane-1,10-diyldi-1 (4 H ) -pyridyl-4-ylidene) bis (octylammonium) dichloride
  • Octenidinum ( Latin )
Molecular formula C 36 H 64 Cl 2 N 4
External identifiers / databases
CAS number
EC number 274-861-8
ECHA InfoCard 100.068.035
PubChem 51166
Wikidata Q1409243
Drug information
ATC code
Drug class

antiseptic

properties
Molar mass 550.90 g mol −1
Physical state

firmly

Melting point

215-217 ° C (dihydrochloride)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-315-319-410
P: 273-280-301 + 312-330-305 + 351 + 338-302 + 352
Toxicological data
  • 800 mg kg −1 ( LD 50 ,  rat ,  oral , dihydrochloride)
  • 10 mg kg −1 ( LD 50 ,  rat ,  iv , dihydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Octenidine dihydrochloride (octenidine) is a non-specific, antimicrobial, cationic active ingredient from the chemical group of bispyridines with a broad action against bacteria , fungi and enveloped viruses . Products containing octenidine are used topically to disinfect skin and mucous membranes, to disinfect wounds, and to decontaminate MRSA .

properties

Octenidine dihydrochloride is colorless and odorless. Octenidine dihydrochloride is mainly used in Europe in a mass fraction of 0.1 to 2.0%, mostly in combination with phenoxyethanol for the disinfection of skin and mucous membrane wounds and for the antiseptic treatment of the mucous membrane of the oral cavity and of the urogenital and anogenital areas, e.g. B. prior operations in the anal - and genital area and in preparation for the laying of a bladder - catheter . Since it does not evaporate, it has a remanence effect . The onset of action is quick compared to other antiseptics, comparable to PVP-iodine . No resistance was found to octenidine dihydrochloride at low doses in MRSA . It is well tolerated by fibroblasts , but is toxic to cartilage tissue . It is not absorbed through the skin . It can therefore also be used during pregnancy and breastfeeding, as well as for new and premature babies.

Spectrum of activity

Octenidine dihydrochloride is bactericidal against both gram-positive and negative bacteria, virucidal against lipophilic (enveloped) viruses such as the herpes simplex viruses and the hepatitis B virus , and microbicidal against Trichomonas vaginalis . It is also fungicidal , but not sporicidal . In yeast , octenidine dihydrochloride destabilizes the cell membrane and causes the cytosol to leak , presumably by inhibiting the biosynthesis of ergosterol .

Contraindications

Octenidine dihydrochloride is not suitable for permanent use. Like polyhexanide, it must not be used on cartilage tissue or in the inner ear or near the eardrum . It is also contraindicated for irrigation of the abdominal cavity and urinary bladder . When using PVP-iodine-based antiseptics at the same time, brownish to purple discoloration of the skin can occur in the border area. When treating stab wounds, for example in the hand area - and generally when treating wound cavities - with octenidine dihydrochloride, care must be taken that the preparation is not applied under pressure (e.g. via a button cannula) and that it can flow off freely (e.g. with the help of a drainage), as otherwise massive edema and tissue damage can occur, which may have to be surgically repaired. When rinsing open wounds of the hand, chronic inflammation and necrosis can occur. In gram-negative bacteria, the use of octenidine dihydrochloride can lead to an increase in resistance to antibiotics , but not in gram-positive bacteria.

Trade names

Trade names for octenidine dihydrochloride are Octenisept (with phenoxyethanol ), Octeniderm (with 1-propanol and 2-propanol ), Octenisept wound gel, Octenident mouth rinse solution, Octeniline wound gel, Octeniline wound rinse solution, Octenisan wash lotion, Octenisan wash gloves, Octenisan wash hoods, Octenisan wash hoods by Schülke & Mayr GmbH .

Individual evidence

  1. ↑ a b c Entry on octenidine dihydrochloride. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2014.
  2. ↑ a b Registration dossier on N, N '- (decane-1,10-diyldi-1 (4H) -pyridyl-4-ylidene) bis (octylammonium) dichlorideTemplate: link text check / apostrophe at the European Chemicals Agency (ECHA), accessed on July 9, 2020.
  3. ↑ Wall Häußers practice of sterilization, antiseptics and preservatives. ISBN 978-3-13-141121-1 )
  4. ↑ NO Hübner et al.: Skin Pharmacol Physiol. 23, 2010, pp. 244-258.
  5. ^ A b T. Koburger, NO Huebner, M. Braun, J. Siebert, A. Kramer: Standardized comparison of antiseptic efficacy of triclosan, PVP-iodine, octenidine dihydrochloride, polyhexanide and chlorhexidine digluconate. In: The Journal of antimicrobial chemotherapy. Volume 65, Number 8, August 2010, pp. 1712-1719, doi : 10.1093 / jac / dkq212 , PMID 20551215 .
  6. ↑ RKI: Recommendation for the prevention and control of methicillin-resistant Staphylococcus aureus strains (MRSA) in medical and nursing facilities. Bundesgesundheitsbl - Health Research - Health Protection 2014, 57, pp. 696–732.
  7. ^ NO Hübner et al in: GMS Hospital Hygiene International. 2009, 4 (2).
  8. ↑ Z. Al-Doori, P. Goroncy-Bermes, CG Gemmell, D. Morrison: Low-level exposure of MRSA to octenidine dihydrochloride does not select for resistance. In: The Journal of antimicrobial chemotherapy. Volume 59, Number 6, June 2007, pp. 1280-1281, doi : 10.1093 / jac / dkm092 , PMID 17439976 .
  9. ↑ G. Müller, A. Kramer: Biocompatibility index of antiseptic agents by parallel assessment of antimicrobial activity and cellular cytotoxicity. In: The Journal of antimicrobial chemotherapy. Volume 61, Number 6, June 2008, pp. 1281-1287, doi : 10.1093 / jac / dkn125 , PMID 18364400 .
  10. Jump up ↑ J. Stahl, M. Braun, J. Siebert, M. Kietzmann: The percutaneous permeation of a combination of 0.1% octenidine dihydrochloride and 2% 2-phenoxyethanol (octenisept®) through skin of different species in vitro. In: BMC veterinary research. Volume 7, August 2011, p. 44, doi : 10.1186 / 1746-6148-7-44 , PMID 21835019 , PMC 3180697 (free full text).
  11. ^ V. Briese, G. Neumann, J. Waldschläger, TW May, J. Siebert, B. Gerber: Efficacy and tolerability of a local acting antiseptic agent in the treatment of vaginal dysbiosis during pregnancy. In: Archives of gynecology and obstetrics. Volume 283, Number 3, March 2011, pp. 585-590, doi : 10.1007 / s00404-010-1414-4 , PMID 20217109 .
  12. ↑ A. Novakov Mikić, S. Stojic: Study results on the use of different therapies for the treatment of vaginitis in hospitalized pregnant women. In: Archives of gynecology and obstetrics. Volume 292, Number 2, August 2015, pp. 371-376, doi : 10.1007 / s00404-015-3638-9 , PMID 25651828 .
  13. ↑ RKI: Recommendation for the prevention of nosocomial infections in neonatal intensive care patients with a birth weight of less than 1500 g . Bundesgesundheitsbl - Health Research - Health Protection 2007, 50, 1265–1303.
  14. ↑ Erik Küng, Jacek Pietrzak, Christoph Klaus, Julia Walochnik: In vitro effect of octenidine dihydrochloride against Trichomonas vaginalis. In: International journal of antimicrobial agents. Volume 47, number 3, March 2016, pp. 232-234, doi : 10.1016 / j.ijantimicag.2015.12.010 , PMID 26899578 .
  15. ↑ Rajendra Prasad, Mahmoud A. Ghannoum: Lipids of Pathogenic Fungi. CRC Press, 1996. ISBN 978-1-351-36095-1 , pp. 243-246.
  16. ↑ Rote Hand Brief: Important information on the drug safety of Octenisept ® (octenidine dihydrochloride, phenoxyethanol) Edematous swellings and tissue damage after being placed under pressure in stab wounds during hand surgery ( Memento from June 17, 2012 in the Internet Archive ), February 7, 2008 (PDF; 171 kB).
  17. ↑ JM Lachapelle: A comparison of the irritant and allergenic properties of antiseptics. In: European journal of dermatology: EJD. Volume 24, number 1, 2014 Jan-Feb, pp. 3–9, doi : 10.1684 / ejd.2013.2198 , PMID 24492204 .
  18. Jump up ↑ CD Biermann, A. Kribs, B. Roth, I. Tantcheva-Poor: Use and Cutaneous Side Effects of Skin Antiseptics in Extremely Low Birth Weight Infants - A Retrospective Survey of the German NICUs. In: Clinical Pediatrics. Volume 228, Number 4, July 2016, pp. 208-212, doi : 10.1055 / s-0042-104122 , PMID 27362412 .
  19. ↑ G. Kampf: Biocidal Agents Used for Disinfection Can Enhance Antibiotic Resistance in Gram-Negative Species. In: Antibiotics. Volume 7, number 4, December 2018, p., Doi : 10.3390 / antibiotics7040110 , PMID 30558235 , PMC 6316403 (free full text).
  20. ↑ G. Kampf: Antibiotic Resistance Can Be Enhanced in Gram-Positive Species by Some Biocidal Agents Used for Disinfection. In: Antibiotics. Volume 8, number 1, February 2019, p., Doi : 10.3390 / antibiotics8010013 , PMID 30717270 , PMC 6466599 (free full text).