| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| Other Sizes |
| Targets |
The active metabolite, sulfacetamide, targets the bacterial enzyme dihydropteroate synthetase. It acts as a competitive antagonist to para-aminobenzoic acid (PABA), inhibiting the synthesis of dihydrofolic acid, a precursor to folic acid, which is essential for bacterial growth.
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|---|---|
| ln Vitro |
In vitro, Phthalylsulfacetamide itself is a prodrug and has limited direct antibacterial activity. Its activity is generated upon its slow decomposition in the intestine to sulfacetamide. Sulfacetamide inhibits the synthesis of folic acid in bacteria, thereby inhibiting their growth.
|
| ln Vivo |
In vivo, Phthalylsulfacetamide is used for the treatment of dysentery, enteritis, and for the prevention of intestinal infections after surgery. As a poorly absorbed drug, it remains in the gastrointestinal tract, where it slowly releases sulfacetamide to exert its local antibacterial effects.
|
| Enzyme Assay |
The in vitro activity of the active metabolite, sulfacetamide, is measured by its ability to inhibit dihydropteroate synthetase. This is typically performed using a biochemical assay where the enzyme is incubated with its substrate, PABA, and the inhibitor, and the production of dihydrofolic acid is measured.
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| Cell Assay |
In vitro cell-based assays are used to determine the antibacterial activity of the released sulfacetamide against susceptible bacteria. Minimum inhibitory concentrations (MICs) are determined by culturing bacteria in the presence of varying concentrations of the compound.
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| Animal Protocol |
In vivo efficacy is evaluated in animal models of intestinal infection. The compound is administered orally, and its ability to reduce bacterial load in the gut and improve clinical symptoms is assessed.
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| ADME/Pharmacokinetics |
Phthalylsulfacetamide is poorly absorbed from the gastrointestinal tract. Its pharmacokinetic properties are characterized by its slow decomposition and local release of sulfacetamide in the intestine, providing a sustained antibacterial effect in the gut with minimal systemic absorption.
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| Toxicity/Toxicokinetics |
The toxicity of Phthalylsulfacetamide is primarily related to its local effects in the intestine and the systemic toxicity of sulfacetamide, which can include allergic reactions and, rarely, serious adverse effects like Stevens-Johnson syndrome. Its poor absorption limits systemic toxicity.
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| Additional Infomation |
Phthalylsulfacetamide belongs to the benzamide class of antibiotics. Phthalylsulfacetamide is a sulfonamide antibiotic used for topical application to the skin and conjunctiva.
Phthalylsulfacetamide is a sulfonamide antibiotic used topically for skin and conjunctival infections and orally for intestinal infections. It is a classic example of a locally acting, poorly absorbed sulfonamide prodrug. It has been largely replaced by other antibiotics with better safety and efficacy profiles. |
| Molecular Formula |
C16H14N2O6S
|
|---|---|
| Molecular Weight |
362.35
|
| Exact Mass |
362.057
|
| CAS # |
131-69-1
|
| PubChem CID |
8574
|
| Appearance |
White to off-white solid powder
|
| Density |
1.478 g/cm3
|
| Melting Point |
196°
|
| Index of Refraction |
1.637
|
| LogP |
3.006
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
25
|
| Complexity |
619
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
S(C1C([H])=C([H])C(=C([H])C=1[H])N([H])C(C1=C([H])C([H])=C([H])C([H])=C1C(=O)O[H])=O)(N([H])C(C([H])([H])[H])=O)(=O)=O
|
| InChi Key |
SNWQKAWITMVCQW-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C16H14N2O6S/c1-10(19)18-25(23,24)12-8-6-11(7-9-12)17-15(20)13-4-2-3-5-14(13)16(21)22/h2-9H,1H3,(H,17,20)(H,18,19)(H,21,22)
|
| Chemical Name |
2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]benzoic acid
|
| Synonyms |
NSC-163977; NSC 163977
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~68.99 mM)
H2O : ~1 mg/mL (~2.76 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.90 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 (6.90 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 (6.90 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 | 2.7598 mL | 13.7988 mL | 27.5976 mL | |
| 5 mM | 0.5520 mL | 2.7598 mL | 5.5195 mL | |
| 10 mM | 0.2760 mL | 1.3799 mL | 2.7598 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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