| Size | Price | Stock | Qty |
|---|---|---|---|
| 10g |
|
||
| 25g |
|
||
| 50g |
|
||
| 100g | |||
| 200g | |||
| Other Sizes |
Purity: ≥98%
Benzethonium chloride (Hyamine, Benzethonium Chloride, Solamine, Disilyn), a synthetic quaternary ammonium salt of Benzethonium, is a potent inhibitor of nAChRs with surfactant, antiseptic, and anti-infective activities. It has been used as a topical antimicrobial agent in first aid antiseptics.
| Targets |
Benzethonium chloride targets cholinesterase (ChE) and acetylcholinesterase (AChE). For ChE with acetylthiocholine as substrate: Ki = 35 nmol/L, Km = 85 μmol/L, Vmax = 2.6 kU/L; α = 1.9. For AChE: Ki = 36 nmol/L, Km = 102 μmol/L, Vmax = 22.5 kU/L; α = 2.2. Mixed-type inhibition (affecting both Vmax and Km) is observed. ChE is about 10-fold more sensitive to inhibition than AChE: 0.203 μmol/L Benzethonium chloride causes 50% decrease in Vmax of ChE, while 2.03 μmol/L causes similar reduction for AChE.[1]
|
|---|---|
| ln Vitro |
In vitro activity: Benzethonium chloride inhibits acetylcholine responses in the α7 nAChRs in a mixed competitive and non-competitive manner but there is no voltage- or use-dependence of the response in either subtype. Benzethonium chloride produces mixed-type inhibition of choline esterase and acetylcholine esterase-affecting both Fmax and Km, Choline esterase is about 10-fold more sensitive to benzethonium chloride than acetylcholine esterase. Benzethonium chloride inhibits ICl(Ca) in response to 0.1 μM acetyl-beta-methylcholine in oocytes expressing m1 muscarinic receptors with IC50 of 0.88 μM. Benzethonium chloride combined with racemic S(+)/R(-) ketamine inhibits muscarinic signaling with a calculated IC50 of 15 μM and a Hill coefficient of 0.6. Benzethonium (5 μM) significantly increases cytosolic Ca(2+)-concentration, decreases forward scatter and triggered annexin V-binding affecting some 30% of the erythrocytes. Benzethonium (5 μM) further significantly enhances the effect of glucose depletion on cytosolic Ca(2+)-concentration and annexin V-binding, but significantly blunts the effect of glucose depletion on forward scatter. Benzethonium (5 μM) significantly enhances lactic acid formation but not ceramide abundance. Benzethonium chloride reduces cell viability with IC50 of 3.8 μM in FaDu, 42.2 μM in NIH 3T3, 5.3 μM in C666-1, and 17.0 μM in GM05757. Benzethonium chloride (9 μM) induces apoptosis and activates caspases after 12 hours in FaDu cells. Benzethonium chloride produces linear mixed-type inhibition of cholinesterase and acetylcholinesterase. Lineweaver-Burk plots intersect above the 1/[S] axis, indicating α>1. For cholinesterase, in the presence of 0.203 μmol/L Benzethonium chloride, Vmax changed to 1.2 kU/L and Km to 128.7 μmol/L. For acetylcholinesterase, 2.03 μmol/L Benzethonium chloride gave Vmax 11.2 kU/L and Km 190 μmol/L. Using butyrylthiocholine as substrate, the wet chemistry method (BM/Hitachi 911) showed 29% inhibition of cholinesterase at 0.203 μmol/L Benzethonium chloride, 87% at 2.03 μmol/L, and 95% at 20.3 μmol/L; at 203 μmol/L activity was unmeasurable. The dry slide method (Ektachem 700 XR) showed no inhibition up to 20.3 μmol/L, and only 9% inhibition at 203 μmol/L, suggesting binding of Benzethonium chloride to slide components prevents it from reaching the enzyme reaction layer.[1] |
| ln Vivo |
Benzethonium chloride (5 mg/kg) ablates the tumor-forming ability of FaDu cells, delays the growth of xenograft tumors, and combined additively with local tumor radiation therapy in established FaDu tumors in SCID mice.
|
| Enzyme Assay |
Cholinesterase and acetylcholinesterase activities were measured on a BM/Hitachi 911 autoanalyzer at 37°C using the method of Lewis et al. with modified protocol.
For cholinesterase: 15 μL plasma samples were added to 280 μL R1 containing 0.58 mmol/L sodium bicarbonate and 0.32 mmol/L 5,5'-dithiobis (2-nitrobenzoic acid) in 0.1 mol/L phosphate buffer (pH 8.0). After 1.25 min, the reaction was started by adding 20 μL of 7.87 mmol/L acetylthiocholine and monitored monochromatically at 415 nm between the 10th and 20th revolutions of the carousel (each revolution 20 s). For acetylcholinesterase: sample volume was 5 μL and R1 was increased to 290 μL. When butyrylthiocholine (7.87 mmol/L) was used as substrate, it replaced acetylthiocholine. Kinetics of inhibition: enzyme activities were determined at final acetylthiocholine concentrations of 15, 25, 50, 80, 120, 160, and 250 μmol/L in the absence and presence of 2.03 and 4.06 μmol/L Benzethonium chloride. R1 was 260 μL for cholinesterase and 270 μL for acetylcholinesterase, R2 was 20 μL isotonic saline or Benzethonium chloride solution, and R3 was acetylthiocholine (20 μL). Protein determination by benzethonium chloride method: 15 μL urine samples were added to 250 μL R1 containing 530 mmol/L NaOH and 74 mmol/L EDTA-Na2. Reaction started by adding 100 μL R2 (32 mmol/L Benzethonium chloride) and monitored bichromatically at 505 nm (primary) and 700 nm (secondary) between the 15th and 31st revolutions. To eliminate carry-over inhibition, the analyzer was programmed to carry out an additional cell wash with 5 mL/L Triton X-100, 10 g/L sodium dodecyl sulphate, or 5 mL/L Tween 20 after protein determination. Washing with 5 mL/L or 10 mL/L Triton X-100 abolished the carry-over inhibitory effect; 10 g/L sodium dodecyl sulphate and 5 mL/L Tween 20 were equally effective. Washing with selective mode solution (0.2 mmol/L HCl) failed to remove the inhibition.[1] |
| Animal Protocol |
Dissolved in PBS; 5 mg/kg; i.p. injection FaDu tumors in SCID mice.
|
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Transdermal absorption is likely negligible. /Benzalkonium chloride/ |
| References |
Eur J Clin Chem Clin Biochem.1997 Aug;35(8):603-7;Clin Cancer Res.2006 Sep 15;12(18):5557-69.
|
| Additional Infomation |
Benzethonium chloride is an odorless white crystal or powder with an extremely bitter taste. A 1% aqueous solution is weakly alkaline to litmus paper. (NTP, 1992)
Benzalkonium chloride is a (synthetic) quaternary ammonium salt with the structure benzyldimethylamine, in which the nitrogen atom is quaternized by 2-{2-[p-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy}ethyl, and the chloride ion is the counterion. It is a preservative and disinfectant, effective against a variety of bacteria, fungi, molds, and viruses. It can be used as a preservative, disinfectant, antibacterial agent, antiviral agent, and antifungal agent. It is a quaternary ammonium salt, chloride, and aromatic ether. A bactericidal cationic quaternary ammonium surfactant used as a topical anti-infective agent. It is an ingredient in pharmaceuticals, deodorants, mouthwashes, etc., used for instrument sterilization in the food processing and pharmaceutical industries, surgical procedures, and can also be used as a preservative. This compound is toxic when ingested and can cause neuromuscular blockade. See also: Benzalkonium chloride (containing the active component); Benzalkonium chloride; Thymol (ingredient); Benzalkonium chloride; Lidocaine (ingredient)... See more... Benzethonium chloride is used in one of the most frequently employed turbidimetric methods for determination of total protein in urine and cerebrospinal fluid. It binds to plastic cuvettes; binding is greater in the presence of protein. The bound Benzethonium chloride is not completely dislodged by routine washing procedures and can complex with enzymes, causing reagent carry-over inhibition. For cholinesterase measured by the dry slide method (Ektachem 700 XR) using butyrylthiocholine as substrate, the assay remains unaffected until Benzethonium chloride concentration exceeds 200 μmol/L. The equilibrium of enzyme (cholinesterase) and inhibitor reaction is in the EI direction (Ki = 36 nmol/L), and inhibitor can be stripped from EI in the dry slide, suggesting reversible, non-covalent binding.[1] |
| Molecular Formula |
C27H42NO2.CL
|
|
|---|---|---|
| Molecular Weight |
448.08
|
|
| Exact Mass |
447.29
|
|
| CAS # |
121-54-0
|
|
| Related CAS # |
Benzethonium-d7 chloride;Benzethonium-d6 chloride
|
|
| PubChem CID |
8478
|
|
| Appearance |
White to off-white solid powder
|
|
| Density |
0.998 g/mL at 20 °C
|
|
| Melting Point |
162-164 °C(lit.)
|
|
| LogP |
6.874
|
|
| Hydrogen Bond Donor Count |
0
|
|
| Hydrogen Bond Acceptor Count |
3
|
|
| Rotatable Bond Count |
12
|
|
| Heavy Atom Count |
31
|
|
| Complexity |
466
|
|
| Defined Atom Stereocenter Count |
0
|
|
| InChi Key |
UREZNYTWGJKWBI-UHFFFAOYSA-M
|
|
| InChi Code |
InChI=1S/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
|
|
| Chemical Name |
N-benzyl-N,N-dimethyl-2-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)ethoxy)ethan-1-aminium chloride
|
|
| Synonyms |
|
|
| 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 (e.g. under nitrogen), avoid exposure to moisture and light. |
|
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
|
|||
|---|---|---|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.58 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 25.0 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: ≥ 2.5 mg/mL (5.58 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (5.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 120 mg/mL (267.81 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2317 mL | 11.1587 mL | 22.3174 mL | |
| 5 mM | 0.4463 mL | 2.2317 mL | 4.4635 mL | |
| 10 mM | 0.2232 mL | 1.1159 mL | 2.2317 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.
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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
COA