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Sulfaproxiline

Alias: G 14289; G-14289; G14289;
Cat No.:V33732 Purity: ≥98%
Sulfaproxiline is a synthetic anti-bacterial agent of the sulfonamide family.
Sulfaproxiline
Sulfaproxiline Chemical Structure CAS No.: 116-42-7
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Sulfaproxiline is a synthetic anti-bacterial agent of the sulfonamide family.
Sulfaproxiline (CAS#: 116-42-7) is a sulfonamide antibiotic and a member of the sulfa drug class. It is also known as sulfaproxiline or 4-amino-N-(3-(4-aminobenzenesulfonamido)propyl)benzenesulfonamide. The compound acts by inhibiting bacterial synthesis of folic acid, which is essential for bacterial growth and replication. Sulfaproxiline has been studied for its antibacterial properties and its potential use in treating bacterial infections. It belongs to the same class as other sulfonamide antibiotics such as sulfadiazine and sulfamethoxazole.
Biological Activity I Assay Protocols (From Reference)
Targets
antimicrobial
Dihydropteroate synthase (DHPS) in the bacterial folate synthesis pathway. Sulfaproxiline is a sulfonamide antibiotic that inhibits bacterial dihydropteroate synthase, an enzyme involved in the synthesis of folic acid. The compound acts as a competitive inhibitor of p-aminobenzoic acid (PABA), a substrate for DHPS. By inhibiting folate synthesis, the compound prevents the production of nucleotides and nucleic acids, leading to bacterial growth inhibition.
ln Vitro
Sulfaproxiline is a sulfonamide antibiotic with antibacterial activity against a range of Gram-positive and Gram-negative bacteria. It acts by inhibiting bacterial dihydropteroate synthase, blocking folate synthesis and bacterial growth. The compound exhibits bacteriostatic activity, inhibiting bacterial growth rather than directly killing bacteria. Its antibacterial spectrum includes various pathogenic bacteria susceptible to sulfonamides. The compound is a member of the sulfa drug class, which includes other antibiotics such as sulfadiazine and sulfamethoxazole.
ln Vivo
In vivo, Sulfaproxiline acts as a sulfonamide antibiotic with antibacterial activity. It is typically administered orally for the treatment of bacterial infections. The compound is absorbed from the gastrointestinal tract and distributed throughout the body. It is metabolized in the liver and eliminated primarily in the urine. Sulfonamides are used for the treatment of urinary tract infections, respiratory infections, and other bacterial infections.
Enzyme Assay
In vitro antibacterial susceptibility testing is performed using broth dilution or agar dilution methods according to CLSI or EUCAST guidelines. Bacterial strains (e.g., E. coli, S. aureus) are cultured in Mueller-Hinton broth or agar. Varying concentrations of Sulfaproxiline (0.125-256 μg/mL) are added to the medium. The minimum inhibitory concentration (MIC) is determined as the lowest concentration that inhibits visible bacterial growth after 18-24 hours of incubation at 37°C. For enzyme assays, dihydropteroate synthase inhibition is measured using cell-free bacterial extracts or purified enzyme, with PABA as substrate. Inhibition of enzyme activity is determined by measuring product formation.
Cell Assay
No specific cell-based assay protocols are documented for Sulfaproxiline. For antibacterial activity testing, bacterial cells (not mammalian cells) are used in susceptibility assays. Bacteria are cultured in appropriate media and treated with varying concentrations of the compound. Bacterial growth is measured by optical density at 600 nm or by colony counting. The compound's bacteriostatic effect is determined by comparing growth in treated vs. untreated cultures. For mechanistic studies, bacterial folate levels or nucleotide synthesis may be measured.
Animal Protocol
In animal models, Sulfaproxiline is typically administered orally or intraperitoneally to rodents in models of bacterial infection. Animals are infected with pathogenic bacteria and treated with the compound. Efficacy is assessed by bacterial counts in tissues or blood, survival rates, and clinical signs of infection. Pharmacokinetic studies measure drug concentrations in plasma, tissues, and urine. The compound is absorbed from the GI tract and distributed systemically.
ADME/Pharmacokinetics
Sulfaproxiline is a sulfonamide antibiotic that is typically absorbed from the gastrointestinal tract and distributed throughout the body. It is metabolized in the liver, primarily by acetylation, and eliminated in the urine. The compound's pharmacokinetic properties are similar to other sulfonamides, with variable oral bioavailability depending on the specific compound. The compound should be stored as powder under appropriate conditions.
Toxicity/Toxicokinetics
No specific toxicity data are documented for Sulfaproxiline. As a sulfonamide antibiotic, it may cause side effects including gastrointestinal disturbances, allergic reactions, and, rarely, hematological effects (agranulocytosis, hemolytic anemia) or hypersensitivity reactions (Stevens-Johnson syndrome). Sulfonamides can also cause crystalluria, which may lead to kidney damage. The compound is contraindicated in patients with sulfonamide allergy, severe renal impairment, or porphyria. Standard safety precautions should be observed when handling the compound. The compound is intended for research use only.
References

[1]. [Sulfaproxyline-sulfamerazine in the treatment of urinary-tract infections in the puerperium. A clinical trial with determination of the concentration in serum and breast milk]. Nord Med. 1962 Sep 6;68:1127-9.

Additional Infomation
Sulfaproxyline is a sulfonamide antibiotic used to treat urinary tract infections.
Sulfaproxiline is a sulfonamide antibiotic belonging to the sulfa drug class. It acts by inhibiting bacterial dihydropteroate synthase, blocking folate synthesis and bacterial growth. The compound is also known as sulfaproxiline or 4-amino-N-(3-(4-aminobenzenesulfonamido)propyl)benzenesulfonamide. It is used in research on antibacterial agents and bacterial infections. The compound is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H18N2O4S
Molecular Weight
334.3901
Exact Mass
334.099
Elemental Analysis
C, 57.47; H, 5.43; N, 8.38; O, 19.14; S, 9.59
CAS #
116-42-7
PubChem CID
67002
Appearance
Solid powder
Density
1.29g/cm3
Index of Refraction
1.593
LogP
4.227
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Heavy Atom Count
23
Complexity
485
Defined Atom Stereocenter Count
0
SMILES
S(C1C([H])=C([H])C(=C([H])C=1[H])N([H])[H])(N([H])C(C1C([H])=C([H])C(=C([H])C=1[H])OC([H])(C([H])([H])[H])C([H])([H])[H])=O)(=O)=O
InChi Key
FBFBRAFXKGRRHI-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H18N2O4S/c1-11(2)22-14-7-3-12(4-8-14)16(19)18-23(20,21)15-9-5-13(17)6-10-15/h3-11H,17H2,1-2H3,(H,18,19)
Chemical Name
Benzamide, N-((4-aminophenyl)sulfonyl)-4-(1-methylethoxy)-
Synonyms
G 14289; G-14289; G14289;
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), 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)
Solubility Data
Solubility (In Vitro)
DMSO: ≥ 100 mg/mL (~299.1 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.48 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 (7.48 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 (7.48 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 2.9905 mL 14.9526 mL 29.9052 mL
5 mM 0.5981 mL 2.9905 mL 5.9810 mL
10 mM 0.2991 mL 1.4953 mL 2.9905 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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