PRODUCTS

OCTENIDINE DIHYDROCHLORIDE

CAS Number: 70775-75-6
EC Number: 274-861-8
Formula: C36H62N4 • 2 HCl
Molecular weight: 623.83 g/mol

Octenidine dihydrochloride is a cationic surfactant, with a gemini-surfactant structure, derived from pyridine.
Octenidine dihydrochloride is active against Gram-positive and Gram-negative bacteria.
Since 1987, Octenidine dihydrochloride has been used primarily in Europe as an antiseptic prior to medical procedures, including on neonates.
Octenidine dihydrochloride is a cationic surfactant and bis-(dihydropyridinyl)-decane derivative used in concentrations of 0.1-2.0% for skin, mucous membrane and wound antisepsis.
Octenidine dihydrochloride is similar in Octenidine dihydrochlorides action to quaternary ammonium compounds, but is of somewhat broader spectrum of activity.
Octenidine is currently increasingly used in continental Europe as a substitute for quats or chlorhexidine in water- or alcohol-based skin, mucosa and wound antiseptics.
In aqueous formulations, Octenidine dihydrochloride is often potentiated with addition of 2-phenoxyethanol.

Uses of Octenidine dihydrochloride:
Since 1987, octenidine has been used in Europe as an antiseptic, in concentrations of 0.1 to 2.0%.
Octenidine dihydrochloride is a substitute for chlorhexidine, with respect to Octenidine dihydrochlorides 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.
They may contain the antiseptic phenoxyethanol.
Octenidine dihydrochloride is not listed in the Annex V of authorized preservatives of the European Cosmetic Regulation 1223/2009.

Applications include:
Salves, creams, lotions
Deos
Vaccines
Oral care
etc.

Octenidine dihydrochloride is a cationic surfactant, with antimicrobial activity against Gram-positive and Gram-negative bacteria.
Octenidine approved as a medicinal substance in several European countries and used for skin antisepsis in combination with aliphatic alcohols, e.g. propan-1-ol and propan-2-ol, or with detergents such as antiseptic soap.
Octenidine is also used for antisepsis on wounds and mucosa either as a single substance, as an approved combination of Octenidine and phenoxyethanol.
Octenidine is virtually not absorbed via the skin or mucous membranes.
Because Octenidine is only approved and used topically and is virtually not absorbed, no systemic effects are to be expected.
Therefore, no further pharmacokinetic studies or studies on behalf of metabolism have been conducted.
Octenidine is easy and safe to handle, chemically stable, not inflammable, without resistance development and low toxicity to man and the environment alike.
Octenidine dihydrochlorides popularity among therapists and wound care specialists is based on good clinical results, easy and pain-free application and local tolerance.
Beside readily available combinations with phenoxyethanol, mouth rinses, and vaginal applications, semi-fluid preparations and dressings are described.

Octenidine dihydrochloride (octenidine) was introduced for skin, mucous membrane and wound antisepsis more than 20 years ago.
Until now, a wealth of knowledge has been gained, including in vitro and animal studies on efficacy, tolerance, safety and clinical experience both from case reports and prospective controlled trials.
Nowadays, octenidine is an established antiseptic in a large field of applications and represents an alternative to older substances such as chlorhexidine, polyvidone-iodine or triclosan.
The review is based on the current literature and unpublished original data as well.

Octenidine dihydrochloride is intended for use in all mammalian food producing species for skin and mucosal disinfection and short-term supportive antiseptic wound treatment as a 0.1% aqueous solution for cutaneous use.
Octenidine dihydrochloride (N,N'-(1,1 0-Decandiyldi-1 (4-H)-pyridynyl-4yliden)bis(1-octanamine)- dihydrochloride - CAS No 70775-75-6) is an antiseptic agent intended for use in all mammalian food producing species for skin and mucosal disinfection and short-term supportive antiseptic wound treatment as a 0.1% aqueous solution for cutaneous use.

Octenidine dihydrochloride belongs to the group of bispyridines.
The active substance has non-specific antimicrobial, antifungal and antiviral properties.
Octenidine dihydrochloride is used for the treatment of wound infections and for disinfecting the skin and mucous membrane.

Octenidine dihydrochloride Applications
Octenidine dihydrochloride is used as a antiseptic for skin, mucous Membranes and wounds.

Octenidine dihydrochloride Solubility
Soluble in dimethyl sulfoxide and methanol.

Octenidine dihydrochloride Notes
Store in cool, well ventilated area.
Keep container tightly closed. Store away from oxidizing agent.

Octenidine dihydrochloride Uses
Octenidine is an antiseptic (topical).
Octenidine is a cationic surfactant and bis-(dihydropyridinyl)-decane derivative.

Octenidine dihydrochloride is an effective antiseptic compound which mode of action is based on destabilization plasma membrane of microorganisms.
This ensures that microorganisms cannot develop the drug resistance in a straightforward way, as the entire cellular structure, rather than specific molecular target is affected.
Since the octenidine is a hydrophobic compound, Octenidine dihydrochloride requires organic solvent such as phenoxyethanol in order to be effectively administered.
However, the presence of phenoxyethanol has strong irritating effect, particularly when applied on open wounds and mucous membranes.
Phospholipids are known as neutral excipients free of side effects and in their aggregated form may serve as solvent for octenidine.
In this article, we propose a new antiseptic formulation composed of equimolar ratio of lipids and octenidine.
The resulting particles are ∼4 nm in diameter showing that their topology is different from that known for liposomes.
The new formulation has proven to be equally effective as octenidine dihydrochloride formulation marketed under the name of Octenisept®.
The main advantage of the new formulation is that Octenidine dihydrochloride does not contain phenoxyethanol, which opens new possibilities for broader application spectrum of octenidine, including treatments of mucous membranes and open wounds.

Chemical Name: Octenidine Dihydrochloride
Synonyms: N,N'-(1,10-Decanediyldi-1(4H)-pyridinyl-4-ylidene)bis-1-octanamine Hydrochloride; Neo Kodan; Octeniderm; Octenidine Hydrochloride; Win 41464-2;
CAS Number: 70775-75-6
Alternate CAS: 71251-02-0-unlabelled
Molecular Formula: C₃₆H₆₄Cl₂N₄
Appearance: White to Off-White Solid
Melting Point: >207ºC (dec.)
Molecular Weight: 623.83
Storage: Hygroscopic, Refrigerator, under inert atmosphere
Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
Stability: Hygroscopic
Category: Standards; Pharmaceutical/API Drug Impurities/Metabolites;
Applications: Octenidine is an antiseptic (topical).
Octenidine is a cationic surfactant and bis-(dihydropyridinyl)-decane derivative.

CAS Number: 70775-75-6
Octenidine: 71251-02-0
CHEBI: 478961
ChEMBL: ChEMBL36342
ChemSpider: 46370
ECHA InfoCard: 100.068.035
EC Number: 274-861-8
PubChem CID: 198481
UNII: U84956NU4B
Octenidine: OZE0372S5A
CompTox Dashboard (EPA): DTXSID90221025

Octenidine dihydrochloride is used as a antiseptic for skin, mucous Membranes and wounds.
Octenidine dihydrochloride (octenidine) was introduced for skin, mucous membrane and wound antisepsis more than 20 years ago.
Until now, a wealth of knowledge has been gained, including in vitro and animal studies on efficacy, tolerance, safety and clinical experience both from case reports and prospective controlled trials.
Nowadays, octenidine is an established antiseptic in a large field of applications and represents an alternative to older substances such as chlorhexidine, polyvidone-iodine or triclosan.
The review is based on the current literature and unpublished original data as well.

The empiric use of antibiotics is being restricted due to the spread of antimicrobial resistance.
However, topical antiseptics are less likely to induce resistance, owing to their unspecific mode of action and the high concentrations in which they can be used.
One such antiseptic, octenidine dihydrochloride (OCT), can be used either prophylactically or therapeutically on the skin, mucosa and wounds.
Evidence to support Octenidine dihydrochlorides use comes from in-vitro, animal and clinical studies on its safety, tolerability and efficacy.
This article summarises the physical, chemical and antimicrobial properties of OCT in the context of wound care.

Octenidine dihydrochloride is a cationic antiseptic that belongs to the bispyridine class of chemicals.
Octenidine dihydrochloride has activity against Gram-positive and Gram-negative bacteria.
Octenidine dihydrochloride was effective in oral hygiene, preventing plaque and gingivitis, as a whole body wash for methicillin-resistant S. aureus decolonization78 and for skin disinfection of premature newborn infants.
Octenidine concentrations of less than 1.5 µM (0.94 µg/mL) reduced each microbial population by more than 99% within 15 minutes.
Staphylococcus epidermidis was the most susceptible of the test organisms, and E. coli and Candida albicans were the least susceptible.
Octenidine was more active than chlorhexidine against each test strain.

Storage: Store at -20°C
M.Wt: 623.83
Cas No.: 70775-75-6
Formula: C36H64Cl2N4
Solubility: ≥41.9 mg/mL in EtOH; ≥8.29 mg/mL in H2O with ultrasonic; ≥9.06 mg/mL in DMSO with ultrasonic
Chemical Name: N,N'-(1,1'-(decane-1,10-diyl)bis(pyridin-1(1H)-yl-4(1H)-ylidene))bis(octan-1-amine) dihydrochloride
SDF: Download SDF
Canonical SMILES: CCCCCCCC/N=C1C=CN(CCCCCCCCCCN2C=C/C(C=C2)=NCCCCCCCC)C=C/1.Cl.Cl
Shipping Condition: Evaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tips: For obtaining a higher solubility, please warm the tube at 37°C and shake Octenidine dihydrochloride in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Octenidine dihydrochloride (OCT) is a widely used antiseptic molecule, promoting skin wound healing accompanied with improved scar quality after surgical procedures.
However, the mechanisms by which OCT is contributing to tissue regeneration are not yet completely clear.
In this study, we have used a superficial wound model by tape stripping of ex vivo human skin.
Protein profiles of wounded skin biopsies treated with OCT-containing hydrogel and the released secretome were analyzed using liquid chromatography-mass spectrometry (LC–MS) and enzyme-linked immunosorbent assay (ELISA), respectively.
Proteomics analysis of OCT-treated skin wounds revealed significant lower levels of key players in tissue remodeling as well as reepithelization after wounding such as pro-inflammatory cytokines (IL-8, IL-6) and matrix-metalloproteinases (MMP1, MMP2, MMP3, MMP9) when compared to controls.
In addition, enzymatic activity of several released MMPs into culture supernatants was significantly lower in OCT-treated samples.
Our data give insights on the mode of action based on which OCT positively influences wound healing and identified anti-inflammatory and protease-inhibitory activities of OCT.

The antimicrobial activity of octenidine hydrochloride (OCT) is maintained when applied to the skin of the hands and feet of cynomolgus monkeys.
Aqueous octenidine, at a concentration of 0.2 to 1.6% reduces resident microflora populations from 90 to 99.98%.
A significant reduction in plaque score is observed on the buccal tooth surfaces after daily topical application of 1% solutions of octenidine and chlorhexidine for 7 d; octenidine is more effective than chlorhexidine.

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

CAS: 70775-75-6
Molecular Formula: C36H64Cl2N4
MDL Number: MFCD01938808
Synonym: N,N'-[Decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene]bis(octylammonium) dichloride

Efficacy
Octenidine dihydrochloride is active against Gram-positive and Gram-negative bacteria.
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.
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.
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.
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.

Octenidine dihydrochloride is an effective antiseptic compound for skin mucous membranes and wounds.

Synonyms:
N,N'-[Decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene]bis(octylammonium) dichloride
N-Octyl-1-[10-(4-octyliminopyridin-1-yl)decyl]pyridin-4-imine
N,N’-(1,10-Decanediyldi-1(4H)-pyridinyl-4-ylidene)bis-1-octanamine hydrochloride
N,N'-(Decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene)bis(octylammonium) dichloride

In the post-antibiotic era the issue of bacterial resistance refers not only to antibiotics themselves but also to common antiseptics like octenidine dihydrochloride (OCT).
This appears as an emerging challenge in terms of preventing staphylococcal infections, which are both potentially severe and easy to transfer horizontally.
Essential oils have shown synergisms both with antibiotics and antiseptics.
Therefore the aim of this study was to investigate the impact of lavender essential oil (LEO) on OCT efficiency towards methicillin-resistant S. aureus strains (MRSA).
The LEO analyzed in this study increased the OCT’s susceptibility against MRSA strains.
Subsequent FTIR analysis revealed cellular wall modifications in MRSA strain cultured in media supplemented with OCT or LEO/OCT.
In conclusion, LEO appears to be a promising candidate for an efficient enhancer of conventional antiseptics.

Antiseptics and disinfectants are used comprehensively in hospitals and in various healthcare fields for a variety of topical and hard-surface applications.
In the past decade, the use of antibiotics is restricted due to the spread of antimicrobial resistance.
Now a days, there is an increased use of topical antiseptics, as these are less likely to induce resistance.
The increased use of these topical antiseptics is attributed to the presence of multiple target sites, an unspecific mode of action and usage in higher concentrations.

Wide use of antiseptics belongs to class of Guanidines.
One such antiseptic that belongs to this class is Octenidine Hydrochloride (OCT).
Octenidine dihydrochloride differs from other Guanidines as the amide and ester structures are not part of the molecule.
Therefore, the toxicologically critical part of the chlorhexidine molecule, 4-chloraniline, cannot be liberated, hence can be used safely.
Octenidine was introduced in 1990 as a mucous membrane antiseptic.
Octenidine dihydrochloride has a broad antimicrobial spectrum and is effective against biofilm-forming organisms including MRSA, plaque-forming bacteria such as Actinomyces and Streptococcus spp, Chlamydia, Mycoplasma.

Ferak is still the only producer in the world that uses a process without carcinogenic solvents.
Octenidine dihydrochloride is already effective at an application concentration of 0.1% in aqueous solution and can be used in the pharmaceutical, biopharmaceutical and cosmetics industries.

Octenidine dihydrochloride readily binds to negatively charged surfaces and can be used either prophylactically or therapeutically on the skin, mucosa and wounds.
Octenidine dihydrochloride is used widely in the medical field as antiseptic in areas of skin, mucous membrane, sterilization of IV catheters and wound disinfectant etc.
In dentistry Octenidine dihydrochloride is used as mouthwash, gutta-percha disinfectant, for biofilm inhibition on restorative materials, as a root canal medicament and root canal irrigant.
Even though Octenidine dihydrochloride has wide applications as per the literature, the knowledge of OCT is still a lacunae in dentistry.
The objective of this paper is to discuss the Octenidine hydrochloride applications, the current evidence of Octenidine dihydrochlorides use and future recommendations in dentistry.

Description: Octenidine is an antimicrobial agent.
Octenidine dihydrochloride is active against a variety of bacteria, including methicillin-sensitive and -resistant S. aureus, vancomycin-resistant Enterococcus, E. faecalis, and S. pneumoniae (MICs = 1-32 mg/L), and the fungus C. albicans (MIC = 1 mg/L).
Octenidine (2 mM) reduces methicillin- or vancomycin-resistant S. aureus biofilm formation.
Topical application of octenidine (1%) reduces dental plaque accumulation in cynomolgus monkeys fed a high-sucrose diet.

A combination of 0.1% octenidine dihydrochloride and 2% 2-phenoxyethanol (octenisept) is a commonly used disinfectant in human medicine.
As porcine skin represents an adequate model for human skin, the effect of octenidine dihydrochloride and phenoxyethanol on wound healing is studied in pigs.
Furthermore, the in vitro percutaneous permeation of the test substances is studied.
The impact of the test formulations on wound healing is examined (A) under non occlusive conditions and (B) in comparison to another disinfectant based on povidone-iodine under occlusive conditions, while wounds are treated daily with the test substances.
The percutaneous permeation of octenidine dihydrochloride and phenoxyethanol is studied in Franz-type diffusion cells with intact skin as well as barrier disrupted after tape stripping.
Compared with povidone-iodine or vehicle treatment as well as untreated control wounds the treatment of wounds with the test formulation has no influence on the healing rate in pigs and does not induce retardation of wound healing.
The in vitro diffusion experiment reveals that octenidine dihydrochloride is only detectable in the acceptor chamber of three-barrier disrupted skin samples.
Phenoxyethanol permeates through intact porcine skin in amounts of 11.3% and through barrier disrupted skin in amounts of 43.9%

The empiric use of antibiotics is being restricted due to the spread of antimicrobial resistance.
However, topical antiseptics are less likely to induce resistance, owing to their unspecific mode of action and the high concentrations in which they can be used.
One such antiseptic, octenidine dihydrochloride (OCT), can be used either prophylactically or therapeutically on the skin, mucosa and wounds.
Evidence to support Octenidine dihydrochlorides use comes from in-vitro, animal and clinical studies on Octenidine dihydrochlorides safety, tolerability and efficacy.
This article summarises the physical, chemical and antimicrobial properties of OCT in the context of wound care.

Octenidine dihydrochloride
1,1'-(1,10-Decandiyl)bis(N-octyl-4(1H)-pyridinimin)dihydrochlorid [German] [ACD/IUPAC Name]
1,1'-(1,10-Decanediyl)bis(N-octyl-4(1H)-pyridinimine) dihydrochloride [ACD/IUPAC Name]
1,1'-(1,10-Décanediyl)bis(N-octyl-4(1H)-pyridinimine), dichlorhydrate [French] [ACD/IUPAC Name]
1,1'-Decamethylenebis(1,4-dihydro-4-(octylimino)pyridine) dihydrochloride
1,1'-Decane-1,10-diylbis[4-(octylamino)pyridinium] dichloride
1-Octanamine, N,N'-(1,10-decanediyldi-1-pyridinyl-4-ylidene)bis-, hydrochloride (1:2) [ACD/Index Name]
265-020-6 [EINECS]
274-861-8 [EINECS]
70775-75-6 [RN]
N,N'-(Decane-1,10-diyldipyridin-1-yl-4-ylidene)dioctan-1-amine dihydrochloride
N,N'-(decane-1,10-diyldipyridin-1-yl-4-ylidene)dioctan-1-aminium dichloride
octenidine hydrochloride
pyridinium, 1,1'-(1,10-decanediyl)bis[4-(octylamino)-, chloride (1:2)
U84956NU4B
UNII:U84956NU4B
Win 41464-2
[70775-75-6]
1,1'-(1,10-Decanediyl)bis(4-(octylamino)pyridinium) dichloride
1,1'-(Decane-1,10-diyl)bis(4-(octylamino)pyridin-1-ium) chloride
1,1'-(Decane-1,10-diyl)bis(4-(octylamino)pyridinium) dichloride
1,1'-(Decane-1,10-diyl)bis(N-octylpyridin-4(1H)-imine) dihydrochloride
1,1'-(decane-1,10-diyl)bis[4-(octylamino)pyridinium] dichloride
1,1'-(Decane-1,10-diyl)bis[4-(octylamino)pyridinium]dichloride
1,10-Bis(4-(octylamino)-1-pyridinium)decane dichloride
1,1-decamethylenebis(1,4-dihydro-4-(octylimino)pyridine)
1-[6-(4-iminio-N-octyl-pyridin-1(4H)-yl)-decyl]pyridin-4(1H)-iminium-N'-octyl- dichloride
1-Octanamine, N,N'-(1,10-decanediyldi-1(4H)-pyridinyl-4-ylidene)bis-, dihydrochloride
4-(OCTYLAMINO)-1-{10-[4-(OCTYLAMINO)PYRIDIN-1-IUM-1-YL]DECYL}PYRIDIN-1-IUM DICHLORIDE
71251-02-0 [RN]
dichloride
DIHYDROGEN N-(1-{10-[4-(OCTYLIMINO)PYRIDIN-1-YL]DECYL}PYRIDIN-4-YLIDENE)OCTAN-1-AMINE DICHLORIDE
MFCD00865987 [MDL number]
MFCD01938808 [MDL number]
MFCD29050406
N-(1-{10-[4-(OCTYLIMINIO)PYRIDIN-1-YL]DECYL}PYRIDIN-4-YLIDENE)OCTAN-1-AMINIUM DICHLORIDE
N,N'-(decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene)bis(octylammonium) dichloride
N,N'-[Decane-1,10-diyldi-1(4H)-pyridyl-4-ylidene]bis(octylammonium) dichloride
N-octyl-1-[10-[4-(octylamino)pyridin-1-ium-1-yl]decyl]pyridin-1-ium-4-amine
N-octyl-1-[10-[4-(octylamino)pyridin-1-ium-1-yl]decyl]pyridin-1-ium-4-amine dichloride
octenidin dihydrochloride
octenidine (dihydrochloride)
octenidine dihydrochloride, 98%
octenidinedihydrochloride
Pyridinium, 1,1'-(1,10-decanediyl)bis(4-(octylamino)-, dichloride
UNII-U84956NU4B