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| 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 |
Typically exists as solid at room temperature
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (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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