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Octenidine dihydrochloride

Cat No.:V29555 Purity: ≥98%
Octenidinedihydrochloride is a topically used antiseptic,antibacterial and antimicrobial agent withactivity against multidrug-resistant Gram-negative pathogens.
Octenidine dihydrochloride
Octenidine dihydrochloride Chemical Structure CAS No.: 70775-75-6
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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5g
10g
25g
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Other Forms of Octenidine dihydrochloride:

  • Octenidine
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Octenidine dihydrochloride is a topically used antiseptic, antibacterial and antimicrobial agent with activity against multidrug-resistant Gram-negative pathogens. It inhibits the expression of biofilm genes and destroys the formation of biofilms.
Octenidine dihydrochloride (CAS 70775-75-6) is a cationic antiseptic agent belonging to the bis-(dihydropyridinyl)-decane derivative class. With a molecular formula of C₃₆H₆₂Cl₂N₄ and a molecular weight of 623.82 g/mol, it is a modern antiseptic widely used for skin, mucous membrane, and wound antisepsis. It exhibits broad-spectrum antimicrobial activity against bacteria, fungi, and some viruses. Its mechanism of action involves disrupting microbial cell membranes, leading to rapid bactericidal effects. Octenidine is effective against multidrug-resistant Gram-negative pathogens and inhibits biofilm gene expression and formation. It is considered a valuable alternative to other antiseptics like chlorhexidine and iodine due to its favorable safety and efficacy profile.
Biological Activity I Assay Protocols (From Reference)
Targets
Octenidine dihydrochloride targets the microbial cell membrane. As a cationic surfactant, it interacts with the negatively charged components of the bacterial cell membrane, disrupting its integrity. This leads to leakage of cellular contents and rapid cell death. Unlike some other antiseptics, octenidine does not target specific proteins or enzymes but acts through a physical-chemical mechanism that is less prone to resistance development. Its activity against biofilms is mediated through the inhibition of biofilm gene expression, preventing the formation of these protective microbial communities. This broad-spectrum, non-specific mechanism makes it effective against a wide range of pathogens, including multidrug-resistant strains.
ln Vitro
Concentrations of octenidine below 1.5 μM (0.94 μg/mL) resulted in a better than 99% reduction in the number of microorganisms tested after 15 minutes. Staphylococcus epidermidis was the most vulnerable of the bacteria examined, whereas Escherichia coli and Candida albicans were the least susceptible [1].
In vitro, Octenidine dihydrochloride demonstrates potent and rapid antimicrobial activity. Concentrations of less than 1.5 μM (0.94 μg/mL) cause a greater than 99% reduction of tested microbial populations within 15 minutes. It is active against a variety of bacteria, including methicillin-sensitive and -resistant Staphylococcus aureus. Its bactericidal activity is measured by exposing microbial cultures to various concentrations of the compound and determining the reduction in viable counts over time. The compound also inhibits biofilm formation. Its activity is not significantly affected by the presence of organic matter, making it suitable for use in wound care.
ln Vivo
When examining the skin of cynomolgus monkeys' hands and feet, octenidine dihydrochloride (OCT) maintained its antibacterial action. The number of resident microbial communities is decreased from 90% to 99.98% by aqueous octenidine at a concentration of 0.2% to 1.6% [1]. On the lateral tooth surfaces of the face, a significant reduction in plaque scores was shown after topical application of 1% octinidine and chlorhexidine solution every day for 7 days; octinidine was more effective than chlorhexidine [2].
In vivo, Octenidine dihydrochloride demonstrates sustained antimicrobial activity upon application to the skin. Aqueous octenidine effectively diminishes resident microflora by 90 to 99.98% at concentrations ranging from 0.2 to 1.6%. It is used clinically as a topical antiseptic for skin, mucous membrane, and wound antisepsis. Its rapid and broad-spectrum activity, combined with good tissue tolerance, makes it a preferred agent for preventing and treating local infections. It is available as a 0.1-2.0% solution for various clinical applications.
Enzyme Assay
In vitro non-cell enzyme/receptor binding assays are not applicable for Octenidine dihydrochloride, as it is a membrane-active agent rather than a specific enzyme inhibitor. Its antimicrobial activity is assessed through standard microbiological susceptibility tests. These include broth microdilution and agar diffusion methods to determine the minimum inhibitory concentration (MIC) against various bacterial and fungal strains. Time-kill assays are used to evaluate the kinetics of its bactericidal activity. Its ability to inhibit biofilm formation can be assessed using crystal violet staining or confocal microscopy.
Cell Assay
In vitro cell-based assays for Octenidine dihydrochloride are used to evaluate its cytotoxicity and safety for topical applications. Mammalian cell lines, such as keratinocytes or fibroblasts, are treated with varying concentrations of the compound, and cell viability is measured using MTT or similar assays. These studies help to determine the therapeutic index of the compound, balancing its antimicrobial efficacy against its potential for tissue irritation. The compound's effects on wound healing can also be studied in cell culture models.
Animal Protocol
In vivo animal studies for Octenidine dihydrochloride are conducted to evaluate its safety and efficacy in wound healing and infection models. The compound is applied topically to animal models with infected wounds or skin abrasions, and its effects on microbial load, wound healing rate, and tissue irritation are assessed. Standard protocols for skin irritation and sensitization are followed to ensure the compound's safety for clinical use. Its efficacy against specific pathogens, such as multidrug-resistant bacteria, can be evaluated in these models.
ADME/Pharmacokinetics
Octenidine dihydrochloride has a molecular weight of 623.82 g/mol and a molecular formula of C₃₆H₆₂Cl₂N₄. It is a cationic surfactant and a bis-(dihydropyridinyl)-decane derivative. The compound is soluble in water and is typically formulated as a 0.1-2.0% aqueous solution for clinical use. It should be stored at room temperature, protected from light. Its stability in solution is good, making it suitable for various formulations.
Toxicity/Toxicokinetics
Octenidine dihydrochloride has a favorable safety profile for topical use. It is well-tolerated on skin and mucous membranes, with low potential for irritation or sensitization. Systemic absorption is minimal, reducing the risk of systemic toxicity. It is not intended for oral or parenteral administration. In rare cases, allergic reactions may occur. The compound is considered safe for use in all age groups, including neonates.
References
[1]. Sedlock DM, et al. Microbicidal activity of octenidine hydrochloride, a new alkanediylbis[pyridine] germicidal agent. Antimicrob Agents Chemother. 1985 Dec;28(6):786-90.
[2]. Emilson CG, et al. Effect of the antibacterial agents octenidine and chlorhexidine on the plaque flora in primates. Scand J Dent Res. 1981 Oct;89(5):384-92
Additional Infomation
Drug Indication
Skin disinfection; Treatment of upper respiratory tract infections; Prevention of oral soft tissue infections
Octenidine dihydrochloride is a modern, broad-spectrum antiseptic used for skin, mucous membrane, and wound antisepsis. It is effective against multidrug-resistant pathogens and inhibits biofilm formation. It is a valuable alternative to other antiseptics like chlorhexidine and iodine. The compound is not a systemic drug and is intended for topical use only. It is approved for clinical use in many countries.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C36H64CL2N4
Molecular Weight
623.8262
Exact Mass
622.45
CAS #
70775-75-6
Related CAS #
Octenidine;71251-02-0
PubChem CID
51166
Appearance
White to off-white solid powder
Boiling Point
609.3ºC at 760 mmHg
Melting Point
215-217ºC
Flash Point
322.3ºC
LogP
3.781
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
25
Heavy Atom Count
42
Complexity
691
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCC/N=C1C=CN(CCCCCCCCCCN(C=C/2)C=CC2=N/CCCCCCCC)C=C/1.Cl.Cl
InChi Key
SMGTYJPMKXNQFY-UHFFFAOYSA-N
InChi Code
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
Chemical Name
N-octyl-1-[10-(4-octyliminopyridin-1-yl)decyl]pyridin-4-imine;dihydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~33.33 mg/mL (~53.43 mM)
DMSO : ~5 mg/mL (~8.02 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 5 mg/mL (8.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 5 mg/mL (8.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 5 mg/mL (8.02 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: ≥ 2.5 mg/mL (4.01 mM) (saturation unknown) in 5% DMSO + 40% PEG300 + 5% Tween80 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 5: ≥ 2.5 mg/mL (4.01 mM) (saturation unknown) in 5% DMSO + 95% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.6030 mL 8.0150 mL 16.0300 mL
5 mM 0.3206 mL 1.6030 mL 3.2060 mL
10 mM 0.1603 mL 0.8015 mL 1.6030 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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