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Hexetidine Racemate (NSC-17764)

Alias: NSC 17764; Hexetidine; NSC-17764; Oraldene; Sterisil; Hexoral; Glypesin; Hextril; Elsix; NSC17764
Cat No.:V5132 Purity: =98.34%
Hexetidine (NSC17764; NSC-17764) is a potent anti-bacterial and anti-fungal agent commonly used in both veterinary and human medicine.
Hexetidine Racemate (NSC-17764)
Hexetidine Racemate (NSC-17764) Chemical Structure CAS No.: 141-94-6
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
5g
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Hexetidine recemate (NSC17764; NSC-17764) is a potent anti-bacterial and anti-fungal agent commonly used in both veterinary and human medicine. Hexetidine destroys fungi by suppressing their ability to grow or reproduce. It is a local anesthetic, astringent and deodorant and has antiplaque effects. Hexetidine is the medicinal ingredient in Sterisol, which is labelled for the symptomatic treatment of: streptococcal pharyngitis ('strep throat'), tonsillitis, pharyngitis, laryngitis, gingivitis, ulcerative stomatitis, oral thrush and Vincent's angina; postoperative hygiene following tonsillectomy, throat or oral surgery. In the UK, hexetidine is the active ingredient in the medicated mouthwash branded Oraldene. In Canada, hexetidine was the active ingredient in the medicated mouthwash branded Steri/sol which has been discontinued. It used to be produced by McNeil Consumer Healthcare, a division of Johnson & Johnson (originally Warner–Lambert, then marketed by Pfizer after its acquisition since 2007). Oraldene contains 0.1 g/100 ml of hexetidine. In some European countries, the gargle solution and mouth spray in bottles of 40 ml named Hexoral (by Mcneil) also contains 0.2% hexetidine as its active compound. In Greece it is called Hexalen mouth wash (also available in spray). Hexetidine can also be found in the mouthwash Bactidol (by Mcneil) which is sold in many Asian countries. In Germany, hexetidine vaginal suppositories branded Vagi-Hex are available to be used for vaginal antisepsis. They are also used in late pregnancy for reducing neonatal infectious mortality and morbidity due to group B streptococcal infections; nonetheless, hexetidine is to be used with care during pregnancy, and its vaginal use is counter-indicated in the first three months of pregnancy

Biological Activity I Assay Protocols (From Reference)
Targets
Antibacterial; antifungal
ln Vitro
Hexetidine-containing mouthwash as a monotherapy or as an adjunct can be used in oral hygiene in the prevention of plaque accumulation and gingival inflammation.[3]
ln Vivo
Reduction in the number of colony-forming units of Candida albicans after immersion of the dentures with chlorhexidine digluconate 0.12% was significantly greater than that of the group using hexetidine 0.1% and those of the control group. Hexetidine 0.1% solution tested for the first time as a product of disinfection of the acrylic dentures showed average results after immersion of 8 night hours for 4 days and was less effective than chlorhexidine digluconate 0.12%.[1]
Animal Protocol
A total of 60 denture wearers (20 men, 40 women; age range 40-80 years) with clinical evidence of DS were randomly divided into 2 test groups and 1 control group. The dentures of each test group were treated by immersion in one of the two mouthwashes while those of the control group were immersed in distilled water. Swab samples from the palatal surfaces of the upper dentures were collected before and after of cleaner use and examined mycologically.[1]
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Because heratodin is cationic, it is absorbed by the mucous membranes and dental plaque after oral administration and is difficult to remove. Human studies using radiolabeled heratodin have shown that after a single mouthwash, heratodin can remain on the oral mucosa for 8 to 10 hours, and its presence can be detected in oral tissues for up to 65 hours after administration.
Toxicity/Toxicokinetics
Toxicological Information
Antidote and Emergency Treatment
Immediate First Aid: Ensure adequate decontamination has been performed. If the patient stops breathing, begin artificial respiration immediately, preferably using a machine on demand, bag-valve-mask, or simple breathing mask (if trained). Perform cardiopulmonary resuscitation (CPR) if necessary. Immediately flush contaminated eyes with running water. Do not induce vomiting. If vomiting occurs, tilt the patient forward or place them in the left lateral decubitus position (head down if possible) to maintain an open airway and prevent aspiration. Keep the patient calm and maintain normal body temperature. Seek medical attention. /Class A and Class B Toxins/
Basic Management: Establish an open airway (using an oropharyngeal or nasopharyngeal airway if necessary). Suction if necessary. Observe for signs of respiratory failure and provide assisted ventilation if necessary. Administer oxygen using a non-invasive breathing mask at a flow rate of 10 to 15 liters per minute. Monitor for pulmonary edema and treat as necessary… Monitor for shock and treat as necessary… Predict seizures and treat as necessary… If eyes become contaminated, rinse immediately with water. During transport, continuously rinse eyes with 0.9% normal saline (NS)... Do not use emetics. If swallowed, rinse mouth; if the patient is able to swallow, has a strong gag reflex, and does not drool, administer 5 mL/kg to 200 mL of water to dilute... After cleansing, cover skin burns with a dry, sterile dressing... /Class A and B Poisons/
Advanced Treatment: For patients with impaired consciousness, severe pulmonary edema, or severe respiratory distress, consider oropharyngeal or nasopharyngeal endotracheal intubation to control the airway. Positive pressure ventilation using a bag-valve-mask may be effective. Consider medical treatment for pulmonary edema... For severe bronchospasm, consider the use of β-receptor agonists, such as salbutamol... Monitor heart rhythm and treat arrhythmias if necessary... Initiate intravenous infusion of 5% glucose solution/SRP: "Keep the vessels open," minimum flow rate. If signs of hypovolemia appear, administer 0.9% normal saline (NS) or lactated Ringer's solution. For hypotension accompanied by signs of hypovolemia, administer fluids with caution. Be alert for signs of fluid overdose… Use diazepam or lorazepam to treat seizures… Use promecaine hydrochloride as an adjunct to eye irrigation…
Non-human toxicity values: Oral LD50 in rats is 610-1430 mg/kg
References
[1]. J Int Oral Health. 2015 Aug;7(8):5-8.
[2]. https://en.wikipedia.org/wiki/Hexetidine
[3]. Int J Dent Hyg . 2011 Aug;9(3):182-90. doi: 10.1111/j.1601-5037.2010.00478.x.
Additional Infomation
1,3-Bis(2-ethylhexyl)-5-methyl-1,3-diazinane-5-amine is an organic nitrogen heterocyclic compound and an organic heteromonocyclic compound. It is a bactericidal and antifungal preservative. It is formulated as a mouthwash at a concentration of 0.1% for the treatment of local infections and oral hygiene. (Excerpt from Martindale Pharmacopoeia, 30th edition, page 797)
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H45N3
Molecular Weight
339.6
Exact Mass
339.361
Elemental Analysis
C, 74.27; H, 13.36; N, 12.37
CAS #
141-94-6
PubChem CID
3607
Appearance
Colorless to light yellow liquid
Density
0.9±0.1 g/cm3
Boiling Point
388.2±0.0 °C at 760 mmHg
Melting Point
Freezing point = 70 °C
Flash Point
175.0±13.8 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.467
LogP
7.15
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
12
Heavy Atom Count
24
Complexity
292
Defined Atom Stereocenter Count
0
SMILES
NC1(C)CN(CC(CC)CCCC)CN(CC(CC)CCCC)C1
InChi Key
DTOUUUZOYKYHEP-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H45N3/c1-6-10-12-19(8-3)14-23-16-21(5,22)17-24(18-23)15-20(9-4)13-11-7-2/h19-20H,6-18,22H2,1-5H3
Chemical Name
5-Amino-1,3-bis(2-ethylhexyl)hexahydro-5-methylpyrimidine
Synonyms
NSC 17764; Hexetidine; NSC-17764; Oraldene; Sterisil; Hexoral; Glypesin; Hextril; Elsix; NSC17764
HS Tariff Code
2934.99.03.00
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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)
DMSO : ~200 mg/mL (~588.93 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.12 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 20.8 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: ≥ 2.08 mg/mL (6.12 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 20.8 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: ≥ 2.08 mg/mL (6.12 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9446 mL 14.7232 mL 29.4464 mL
5 mM 0.5889 mL 2.9446 mL 5.8893 mL
10 mM 0.2945 mL 1.4723 mL 2.9446 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.

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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?
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  • 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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.

Clinical Trial Information
Decolonization of patients carrying S. aureus before cardiac surgery: study of the risk factors associated with failure
EudraCT: 2018-001505-90
Phase: Phase 4
Status: Completed
Date: 2018-10-01
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