| Size | Price | Stock | Qty |
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| 25g |
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| Other Sizes |
| Targets |
Dihydropteroate synthase (DHPS), an enzyme in the bacterial folate synthesis pathway. Sulfabenzamide is a sulfonamide antibiotic that acts as a competitive inhibitor of DHPS. The compound is structurally similar to para-aminobenzoic acid (PABA), the natural substrate of DHPS. By mimicking PABA, Sulfabenzamide binds to the active site of DHPS and blocks the enzyme's ability to catalyze the formation of dihydropteroate, a precursor to folic acid. This inhibition disrupts the bacterial synthesis of folate, which is crucial for the production of nucleic acids (DNA and RNA) and proteins. As a result, bacterial growth and replication are halted, leading to a bacteriostatic effect. Because mammalian cells do not synthesize folate but obtain it from dietary sources, they are unaffected by this mechanism of action, which contributes to the selective toxicity of sulfonamides.
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| ln Vitro |
Sulfabenzamide exhibits broad-spectrum antibacterial activity in vitro against a variety of Gram-positive and Gram-negative bacteria. Its activity is primarily bacteriostatic, meaning it inhibits bacterial growth rather than directly killing the bacteria. The compound's effectiveness is often evaluated by determining its minimum inhibitory concentration (MIC) against specific bacterial strains. It is typically used in combination with other sulfonamides, such as sulfathiazole and sulfacetamide, to achieve a synergistic antibacterial effect. This combination is particularly effective against pathogens responsible for vaginal infections. The compound's physicochemical properties, including a LogP of 1.19 and a melting point of 180-184°C, are well-characterized. Its high solubility in DMSO (100 mg/mL) facilitates its use in various in vitro experimental setups.
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| ln Vivo |
Sulfabenzamide's in vivo activity is primarily as a topical antibacterial agent. When applied topically, it is effective in reducing the bacterial load in the vaginal tract, particularly in the treatment of bacterial vaginosis. It is often used in combination with other sulfonamides to enhance its spectrum of activity. The compound is poorly absorbed from the vaginal mucosa, which limits systemic exposure and reduces the risk of side effects. This localized action makes it a suitable choice for treating superficial infections. The compound's efficacy in vivo has been demonstrated in clinical settings, where it is used as part of a triple-sulfa cream or suppository. The combination of sulfabenzamide, sulfathiazole, and sulfacetamide is a well-established treatment for bacterial vaginosis.
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| Enzyme Assay |
In vitro antimicrobial susceptibility testing is the primary method for evaluating Sulfabenzamide's activity. The minimum inhibitory concentration (MIC) is determined using broth dilution or agar dilution methods according to CLSI guidelines. A range of bacterial strains, including both Gram-positive (e.g., Staphylococcus aureus) and Gram-negative (e.g., Escherichia coli), are tested. The compound is dissolved in a suitable solvent, typically DMSO, and then serially diluted in growth medium. The bacterial inoculum is added, and the plates are incubated at 37°C for 18-24 hours. The MIC is the lowest concentration of the compound that inhibits visible bacterial growth. The compound's effectiveness against specific bacterial strains can be compared to other sulfonamides.
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| Cell Assay |
In vitro cell-based assays for Sulfabenzamide are not as common as antimicrobial susceptibility testing, as its primary target is bacterial, not mammalian, cells. However, cytotoxicity assays can be performed to evaluate its safety profile. Mammalian cell lines (e.g., HeLa or HEK293 cells) are treated with varying concentrations of Sulfabenzamide for 24-72 hours. Cell viability is then measured using a colorimetric assay such as MTT or CCK-8. The concentration that reduces cell viability by 50% (IC50) is calculated. These assays help to determine the compound's selectivity and potential for toxicity. The compound's effects on mammalian cell function, such as proliferation or gene expression, can also be studied.
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| Animal Protocol |
In vivo animal studies for Sulfabenzamide are typically conducted to evaluate its efficacy and safety as a topical antibacterial agent. A common model is the vaginal infection model in rodents, where the animals are infected with a pathogenic bacterium (e.g., Gardnerella vaginalis). The compound, often in combination with other sulfonamides, is administered intravaginally. The efficacy is assessed by monitoring the reduction in bacterial counts in the vaginal tract, as well as by evaluating clinical signs of infection. Histological analysis of vaginal tissue can also be performed to assess the degree of inflammation and tissue damage. These studies provide valuable information on the compound's in vivo efficacy and safety.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Sulfabenzamide are characterized by its poor systemic absorption following topical application. When administered intravaginally, the compound remains localized in the vaginal tract, achieving high local concentrations while minimizing systemic exposure. This reduces the risk of systemic side effects. The compound is metabolized in the liver and excreted in the urine. Its oral bioavailability is low, and it is not typically administered systemically. For research purposes, it is soluble in DMSO at 100 mg/mL and can be formulated for topical application. The compound should be stored as a powder at -20°C for up to three years.
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| Toxicity/Toxicokinetics |
The toxicological profile of Sulfabenzamide is consistent with other sulfonamide antibiotics. It is generally well-tolerated when used topically. However, allergic reactions, such as skin rashes, can occur in individuals with sulfonamide hypersensitivity. Systemic absorption is minimal, so the risk of serious side effects is low. In laboratory settings, standard safety precautions should be observed when handling the compound, including the use of personal protective equipment (gloves, lab coat, safety goggles). It is intended for research use only and is not for human therapeutic or diagnostic use.
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| Additional Infomation |
Sulfabenzamide is a sulfonamide compound containing a benzamide substituent on the nitrogen atom. It is an antibacterial/antimicrobial drug, often used in combination with sulfathiazole and sulfacetamide sodium as a topical vaginal antibacterial agent. It is both an antibacterial and antimicrobial agent. It is a sulfonamide compound, belonging to the benzene class, and is also a sulfonamide antibiotic. Sulfabenzamide is an antibacterial agent, often used in combination with sulfathiazole and sulfacetamide sodium as a topical vaginal antibacterial agent. Sulfabenzamide is a sulfonamide antibacterial agent that can be used alone or in combination with sulfathiazole and sulfacetamide sodium as a topical vaginal antibacterial agent.
Sulfabenzamide is a sulfonamide antibacterial agent. It is also known as N-Sulfanilylbenzamide. The compound is often used in combination with sulfathiazole and sulfacetamide sodium as a topical vaginal antibacterial agent. It is effective against a broad spectrum of Gram-positive and Gram-negative bacterial strains. Sulfabenzamide has a molecular formula of C₁₃H₁₂N₂O₃S and a molecular weight of 276.31 g/mol. It is supplied as a white to off-white solid powder with a purity of ≥98%. The compound is soluble in DMSO at 100 mg/mL. Sulfabenzamide is for research use only. |
| Molecular Formula |
C13H12N2O3S
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|---|---|
| Molecular Weight |
276.3110
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| Exact Mass |
276.056
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| CAS # |
127-71-9
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| Related CAS # |
Sulfabenzamide-d4;2732981-22-3
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| PubChem CID |
5319
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Melting Point |
180-184 °C
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| Index of Refraction |
1.636
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| LogP |
1.19
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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 |
3
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| Heavy Atom Count |
19
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| Complexity |
402
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S(C1C([H])=C([H])C(=C([H])C=1[H])N([H])[H])(N([H])C(C1C([H])=C([H])C([H])=C([H])C=1[H])=O)(=O)=O
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| InChi Key |
PBCZLFBEBARBBI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H12N2O3S/c14-11-6-8-12(9-7-11)19(17,18)15-13(16)10-4-2-1-3-5-10/h1-9H,14H2,(H,15,16)
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| Chemical Name |
N-(4-aminophenyl)sulfonylbenzamide
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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 (~361.91 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.05 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 (9.05 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 (9.05 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 | 3.6191 mL | 18.0956 mL | 36.1912 mL | |
| 5 mM | 0.7238 mL | 3.6191 mL | 7.2382 mL | |
| 10 mM | 0.3619 mL | 1.8096 mL | 3.6191 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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