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| Other Sizes |
| Targets |
The primary molecular targets of N-Acetylsulfanilamide include the bacterial enzyme dihydropteroate synthetase, where it acts as a competitive inhibitor. This enzyme is crucial for folic acid synthesis in bacteria. The compound also acts as a carbonic anhydrase inhibitor, binding to the enzyme's active site. As a sulfonamide antibiotic, its antibacterial effects are exerted through inhibition of folic acid synthesis, disrupting bacterial growth and replication.
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| ln Vitro |
In vitro, N-Acetylsulfanilamide demonstrates antibacterial activity as a competitive inhibitor of dihydropteroate synthetase, blocking folic acid synthesis in bacteria. It also shows carbonic anhydrase inhibitory activity. As a metabolite of the herbicide asulam and the antibiotic sulfanilamide, it is formed from asulam by conversion to sulfanilamide via intestinal microflora, followed by N4-acetylation in the liver. Specific potency data such as IC₅₀ values are not detailed.
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| ln Vivo |
Specific in vivo activity data for N-Acetylsulfanilamide are limited. The compound has been used topically to treat skin infections and orally for urinary tract infections. As a sulfonamide antibiotic, it would be expected to exert antibacterial effects in vivo through inhibition of folic acid synthesis. As a metabolite of asulam and sulfanilamide, it may contribute to the pharmacological effects of these parent compounds. However, systematic in vivo studies of the isolated compound are not detailed.
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| Enzyme Assay |
Typical in vitro assays for N-Acetylsulfanilamide include dihydropteroate synthetase inhibition assays, where the enzyme is incubated with p-aminobenzoic acid (PABA) substrate and various concentrations of the compound, and folic acid production is measured. Carbonic anhydrase inhibition assays measure the enzyme's activity in the presence of the compound. Antimicrobial susceptibility tests (broth microdilution) can be used to determine MIC values against bacterial strains. These protocols are for reference only.
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| Cell Assay |
Cellular assays for N-Acetylsulfanilamide are not extensively documented. As an antibacterial agent, standard bacterial culture assays can be employed where bacterial strains are treated with the compound at various concentrations, and growth inhibition is measured by optical density or colony counting. For carbonic anhydrase inhibition, cell lines expressing the enzyme can be treated with the compound, and enzyme activity is measured in cell lysates.
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| Animal Protocol |
In vivo animal experiments for N-Acetylsulfanilamide are not detailed in the available literature. As a sulfonamide antibiotic, standard efficacy studies in animal models of infection could be performed. However, specific protocols including dosing regimens and endpoints are not available in the consulted sources. The compound is primarily used as a research chemical and analytical standard.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for N-Acetylsulfanilamide are limited. As a metabolite of asulam and sulfanilamide, it is formed in the liver via N4-acetylation. With a molecular weight of 214.24 g/mol, it would be expected to have reasonable oral bioavailability. However, detailed ADME parameters are not available. The compound is a sulfonamide derivative and would be expected to be excreted primarily in urine.
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| Toxicity/Toxicokinetics |
Toxicological data for N-Acetylsulfanilamide are limited. As a sulfonamide derivative, it may have similar toxicity profiles to other sulfonamides, including potential for hypersensitivity reactions, crystalluria, and hematological effects. However, comprehensive toxicological studies have not been reported. Standard laboratory safety precautions should be followed when handling the compound. It is intended for research use only.
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| References |
[1]. Edith Ju-Hwa Chu, et al. Syntheses of Compounds Related to Vitamin K. III. 4-(3'-Methyl-4'-hydroxynaphthylazo)-benzenesulfonamide and Related Compounds1,2. Journal of the American Chemical Society 1945 67 (5), 811-812.
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| Additional Infomation |
An antibacterial agent that can be used externally to treat skin infections and orally to treat urinary tract infections.
N-Acetylsulfanilamide (4-Acetamidobenzenesulfonamide) is a sulfonamide derivative with antibacterial and carbonic anhydrase inhibitory activities. It is a metabolite of the herbicide asulam and the antibiotic sulfanilamide, formed by conversion to sulfanilamide via intestinal microflora followed by hepatic N4-acetylation. It has been used topically for skin infections and orally for urinary tract infections. It is a research compound and is not approved as a primary therapeutic agent. |
| Molecular Formula |
C8H10N2O3S
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|---|---|
| Molecular Weight |
214.24
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| Exact Mass |
214.041
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| CAS # |
121-61-9
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| Related CAS # |
N-Acetylsulfanilamide-13C6;1655498-04-6
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| PubChem CID |
8482
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| Appearance |
White to off-white solid
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| Density |
1.414g/cm3
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| Melting Point |
214-217 °C
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| Index of Refraction |
1.605
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| LogP |
2.146
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
299
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(NC1=CC=C(S(=O)(N)=O)C=C1)=O
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| InChi Key |
PKOFBDHYTMYVGJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H10N2O3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11)(H2,9,12,13)
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| Chemical Name |
N-(4-sulfamoylphenyl)acetamide
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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: ~66.7 mg/mL (~311.2 mM; with ultrasonication)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.67 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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 (11.67 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 DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (11.67 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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.6677 mL | 23.3383 mL | 46.6766 mL | |
| 5 mM | 0.9335 mL | 4.6677 mL | 9.3353 mL | |
| 10 mM | 0.4668 mL | 2.3338 mL | 4.6677 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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