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| Targets |
Tosylchloramide sodium trihydrate targets microbial cells through its strong oxidizing properties. As a source of electrophilic chlorine, it reacts with and oxidizes essential cellular components such as proteins, enzymes, and nucleic acids, leading to cell death. This mechanism makes it effective against a broad spectrum of microorganisms, including bacteria, fungi, and viruses. The compound's antimicrobial activity is not target-specific in the traditional sense of a drug-receptor interaction but is a chemical process of oxidation and chlorination. In organic synthesis, it serves as a reagent for various transformations, including the oxidation of alcohols and the chlorination of organic compounds.
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| ln Vitro |
Following treatment with tosyl chloride, Gram-positive bacterial growth was inhibited by 95% to 100%, regardless of dose, with or without serum. E. coli (Gram-negative; with/without serum) was decreased by 94% to 100% at antimicrobial doses of 300 and 400 ppm. At a concentration of 200 ppm, E. coli growth was totally suppressed without serum and 50% inhibited with serum. At 100 and 200 ppm, cell viability remained above 90% under all testing conditions. Exposure to 300 ppm tosyl chloride for 3 minutes can result in cell viability as high as 70%, with longer exposure leading to reduced viability. Serum does not influence cell viability under any conditions [1].
In vitro, Tosylchloramide sodium trihydrate exhibits potent antimicrobial activity. Its efficacy is demonstrated by its ability to kill or inhibit the growth of a wide range of microorganisms in standard antimicrobial susceptibility tests. The compound is used as a disinfectant in various in vitro settings, including laboratory decontamination and surface sterilization. Its activity is concentration- and time-dependent, with higher concentrations and longer exposure times leading to more rapid and complete microbial killing. The compound's oxidizing properties make it an effective biocide in aqueous solutions. |
| ln Vivo |
Rat tissues surrounding the terminal airways of the lungs of both male and female rats showed significant dose-dependent DNA damage and inflammation [2]. Toxic to crayfish, a twenty-four-hour exposure to 50 mg/L of chloramine-T causes significant energy losses that manifest during future physical stress [3]. Through metabolic activation and/or the build-up of reactive metabolites, tosyl chloride may increase the toxicity of numerous xenobiotics. The activity of CYP2E1, CYP1A1/2, CYP2B1/2, CYP3A4, and CYP4A1/2 enzymes were considerably elevated in a dose-dependent manner following treatment with tosyl chloride at 2.50, 5 and 10 mg/kg body weight/day. After receiving 1.25 mg/kg body weight/day of tosyl chloride therapy, this effect was not noticed [4].
In vivo, Tosylchloramide sodium trihydrate is not used as a systemic therapeutic agent due to its toxicity. Its primary in vivo application is as a topical disinfectant for wound cleaning and skin antisepsis. The compound's strong oxidizing properties, while effective for disinfection, are not suitable for internal use. When applied topically, it releases active chlorine, which rapidly kills bacteria on the skin surface and in wounds. Its use in hospitals and clinical settings is well-established for surface and instrument disinfection. |
| Enzyme Assay |
In vitro non-cell enzyme/receptor binding assays are not applicable for Tosylchloramide sodium trihydrate, as it is not a drug that interacts with specific biological targets. Its activity is assessed through chemical and microbiological assays. For example, its oxidizing capacity can be measured by iodometric titration, which quantifies the amount of active chlorine it releases. Its antimicrobial efficacy is evaluated using standard broth dilution or agar diffusion methods to determine the minimum inhibitory concentration (MIC) against various microorganisms. These assays are used for quality control and to ensure the compound's effectiveness as a disinfectant.
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| Cell Assay |
In vitro cell-based assays for Tosylchloramide sodium trihydrate are limited to cytotoxicity studies, as it is not intended for therapeutic use. Its cytotoxic effects on mammalian cells can be assessed in cell culture to evaluate its safety for topical applications. Cells are treated with varying concentrations of the compound, and cell viability is measured using MTT or similar assays. These studies help to determine the concentration range that is microbicidal while being minimally toxic to skin cells. The compound's mechanism of cell killing is primarily through oxidative damage.
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| Animal Protocol |
In vivo animal studies for Tosylchloramide sodium trihydrate are primarily toxicological and are conducted to assess its safety for topical use. These studies involve applying the compound to the skin or wounds of animal models and evaluating local irritation, sensitization, and systemic toxicity. The compound's effects on wound healing and its potential for absorption through the skin are also assessed. Standard protocols for skin irritation and sensitization tests are followed to ensure the compound's safety for use in humans.
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| ADME/Pharmacokinetics |
Tosylchloramide sodium trihydrate has a molecular weight of 281.69 g/mol and a molecular formula of C₇H₇ClNNaO₂S·3H₂O. It is a white to off-white crystalline powder. The compound is soluble in water, and its aqueous solutions are used for disinfection purposes. It should be stored in a cool, dry place, protected from light and moisture, to maintain its stability and activity. Its decomposition can be accelerated by heat, light, and contaminants. The compound has a characteristic odor of chlorine.
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| Toxicity/Toxicokinetics |
Tosylchloramide sodium trihydrate is classified as a skin and eye irritant and can be harmful if ingested or inhaled. It is a strong oxidizing agent and can react with combustible materials, posing a fire hazard. Appropriate safety precautions, including the use of personal protective equipment (gloves, goggles, lab coat), should be taken when handling this compound. It should be used in a well-ventilated area. In case of contact with skin or eyes, immediate rinsing with plenty of water is recommended. The compound is toxic to aquatic life.
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| References |
[1]. Kloth LC, et al. Bactericidal and cytotoxic effects of chloramine-T on wound pathogens and human fibroblasts in vitro. Adv Skin Wound Care. 2007 Jun;20(6):331-45.
[2]. Shim I, et al. Inhalation exposure to chloramine T induces DNA damage and inflammation in lung of Sprague-Dawley rats. J Toxicol Sci. 2013;38(6):937-46. [3]. Kuklina I, et al. Investigation of chloramine-T impact on crayfish Astacus leptodactylus (Esch., 1823) cardiac activity. Environ Sci Pollut Res Int. 2014 Sep;21(17):10262-9. [4]. Martínez MA, et al. Induction of cytochrome P450-dependent mixed function oxidase activities and peroxisome proliferation by chloramine-T in male rat liver. Food Chem Toxicol. 2017 Aug;106(Pt A):86-91 |
| Additional Infomation |
See also: Anhydrous chloramine-t (with active moiety).
Tosylchloramide sodium trihydrate (Chloramine-T sodium trihydrate) is a widely used disinfectant and biocide in laboratories, kitchens, and hospitals. It is also known as N-Chloro-4-toluenesulfonamide sodium salt. The compound acts as a source of electrophilic chlorine in organic synthesis and is used in analytical chemistry for the detection of halogens and bromates. Its strong antimicrobial properties make it effective against a wide range of pathogens. It is not a therapeutic drug and is not intended for human or veterinary use as a systemic agent. Its primary applications are in disinfection, sanitation, and as a chemical reagent. |
| Molecular Formula |
C7H13CLNNAO5S
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| Molecular Weight |
281.6896
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| Exact Mass |
281.01
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| CAS # |
7080-50-4
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| PubChem CID |
517414
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| Appearance |
White to off-white solid powder
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| Melting Point |
167-170 °C(lit.)
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| Flash Point |
92 °C
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| LogP |
3.099
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
16
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| Complexity |
231
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl[N-]S(C1C([H])=C([H])C(C([H])([H])[H])=C([H])C=1[H])(=O)=O.[Na+].O([H])[H].O([H])[H].O([H])[H]
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| InChi Key |
NZYOAGBNMCVQIV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H7ClNO2S.Na.3H2O/c1-6-2-4-7(5-3-6)12(10,11)9-8;;;;/h2-5H,1H3;;3*1H2/q-1;+1;;;
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| Chemical Name |
sodium;chloro-(4-methylphenyl)sulfonylazanide;trihydrate
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~355.00 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.88 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 (8.88 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 (8.88 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5500 mL | 17.7500 mL | 35.5000 mL | |
| 5 mM | 0.7100 mL | 3.5500 mL | 7.1000 mL | |
| 10 mM | 0.3550 mL | 1.7750 mL | 3.5500 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.
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