Octenidine dihydrochloride

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
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).

Octenidine dihydrochloride is a

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.

Medical uses

Since 1987, octenidine has been used in Europe as an

4-chloroaniline.[citation needed
] 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

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

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,

aseptic necrosis and chronic inflammation in penetrating hand wounds in humans.[11][12]

References

  1. ECHA
  2. ^ https://www.ema.europa.eu/documents/psusa/octenidine-list-nationally-authorised-medicinal-products-psusa/00010748/202007_en.pdf [bare URL PDF]
  3. PMID 17439976
    .
  4. ^
    S2CID 5099338.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link
    )
  5. PMID 3909955
    .
  6. ^
    doi:10.1002/14356007.a08_551
  7. PMID 27234462
    .
  8. PMID 26605135
    .
  9. S2CID 19546288
    .
  10. S2CID 80926611
    .
  11. PMID 24492204
    .
  12. S2CID 29175202
    .
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