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| Other Sizes |
| Targets |
The primary target of cyclamic acid sodium is carbonic anhydrase, an enzyme that catalyzes the reversible hydration of carbon dioxide. Inhibition of carbonic anhydrase affects various physiological processes including acid-base balance and ion transport. The compound has also been shown to affect BMP2 signaling in osteoblasts. Its sweetening activity is mediated through activation of sweet taste receptors (T1R2/T1R3), though the exact binding mechanism remains incompletely understood.
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| ln Vitro |
In vitro studies demonstrate that cyclamic acid sodium (12-24 mM; 89 days) causes progressive urothelial abnormalities and focal necrosis in rat bladder organs. It is toxic to osteoblasts, inhibiting cell proliferation, inducing apoptosis, and reducing cell mineralization at concentrations of 0-0.10 μM over 24-72 hours. The compound also decreases BMP2 expression in osteoblasts. However, cyclamic acid sodium has no effect on arginine-induced insulin and glucagon secretion.
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| ln Vivo |
In vivo studies show that cyclamic acid sodium (6000 mg/kg/day; intraperitoneal injection; for 5 days) can successfully establish an acute DILI (drug-induced liver injury) mouse model. The toxicity to the liver shows dose-response and time-response relationships. Cyclamic acid sodium-induced liver, heart, and kidney injury are closely related to the inflammatory response mediated by TNF-α and IL-1β. The compound also demonstrates moderate anticonvulsant activity in maximal electroshock seizure models.
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| Enzyme Assay |
Non-cellular enzyme inhibition assays for cyclamic acid sodium typically involve measuring carbonic anhydrase activity using standard esterase or hydration assays. The compound's ability to inhibit the enzyme is assessed by monitoring the rate of p-nitrophenyl acetate hydrolysis or CO2 hydration. IC50 values are determined by testing a range of inhibitor concentrations in cell-free systems. These assays allow for direct characterization of the compound's interaction with carbonic anhydrase without cellular interference.
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| Cell Assay |
Cellular assays for cyclamic acid sodium utilize osteoblast cell lines to assess cytotoxicity and effects on mineralization. Cells are treated with concentrations ranging from 0 to 0.10 μM for 24-72 hours. Cell proliferation is measured using MTT or CCK-8 assays, while apoptosis is evaluated through flow cytometry with Annexin V/PI staining. Mineralization capacity is assessed using Alizarin Red S staining, and BMP2 expression is analyzed by Western blotting or qPCR.
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| Animal Protocol |
In vivo animal experiments for cyclamic acid sodium typically use rodent models. In one protocol, mice are treated with 6000 mg/kg/day via intraperitoneal injection for 5 days to induce acute drug-induced liver injury. Liver, heart, and kidney tissues are collected for histopathological examination and biochemical analysis. Inflammatory markers such as TNF-α and IL-1β are measured to assess the inflammatory response. Anticonvulsant activity is evaluated using maximal electroshock seizure models.
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| ADME/Pharmacokinetics |
Cyclamic acid sodium is readily soluble in water (45.0 mg/mL) and has limited solubility in DMSO (7.5 mg/mL). For in vivo formulations, it can be prepared in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline at 1 mg/mL. The compound is stable as a powder at -20°C for up to 3 years and in solvent at -80°C for 1 year. It is absorbed from the gastrointestinal tract and undergoes minimal metabolism before renal excretion.
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| Toxicity/Toxicokinetics |
Cyclamic acid sodium has been extensively studied for its toxicological profile. It is toxic to osteoblasts and can inhibit cell proliferation, induce apoptosis, and reduce cell mineralization. The compound causes focal necrosis of bladder organs in rats in vitro, which can promote bladder cancer. However, some studies have shown that low doses have no carcinogenic effect. High-dose administration (6000 mg/kg/day) induces liver, heart, and kidney injury through TNF-α and IL-1β-mediated inflammatory responses.
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| References | |
| Additional Infomation |
Sodium cyclohexylsulfamate is a tasteless or nearly tasteless white crystal or crystalline powder. It has a very strong sweet taste even in dilute solutions. pH (10% aqueous solution): 5.5-7.5. It is used as a non-nutritive sweetener. Cyclohexylsulfamate is an organic molecular entity. Salts and esters of cyclohexylsulfamate.
Cyclamic acid sodium is approved as a food additive (artificial sweetener) in many countries, though its use is banned in the United States. It has no approved therapeutic indications. The compound is used in cancer research and as a tool to study carbonic anhydrase inhibition. Its sweetening activity is approximately 30-50 times that of sucrose. Ongoing research continues to investigate its safety profile and potential applications in seizure disorders. |
| Molecular Formula |
C6H12NNAO3S
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|---|---|
| Molecular Weight |
201.22
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| Exact Mass |
201.043
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| CAS # |
139-05-9
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| Related CAS # |
Cyclamic acid;100-88-9
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| PubChem CID |
23665706
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| Appearance |
White to off-white solid powder
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| Density |
1.32g/cm3
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| Melting Point |
509 °F (decomposes) (NTP, 1992)
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| LogP |
1.84
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
205
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S(N([H])C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H])(=O)(=O)[O-].[Na+]
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| InChi Key |
UDIPTWFVPPPURJ-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C6H13NO3S.Na/c8-11(9,10)7-6-4-2-1-3-5-6;/h6-7H,1-5H2,(H,8,9,10);/q;+1/p-1
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| Chemical Name |
sodium;N-cyclohexylsulfamate
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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 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)
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| Solubility (In Vitro) |
H2O: 50 mg/mL (248.48 mM)
DMSO: 20 mg/mL (99.39 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2 mg/mL (9.94 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 20.0 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 mg/mL (9.94 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 20.0 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 mg/mL (9.94 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 | 4.9697 mL | 24.8484 mL | 49.6968 mL | |
| 5 mM | 0.9939 mL | 4.9697 mL | 9.9394 mL | |
| 10 mM | 0.4970 mL | 2.4848 mL | 4.9697 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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