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| Other Sizes |
| Targets |
The mechanism of action of sulfaguanidine involves the competitive inhibition of dihydropteroate synthase, an essential enzyme in the bacterial folic acid synthesis pathway. By inhibiting this enzyme, it prevents the synthesis of folic acid, which is necessary for bacterial growth and replication. Sulfaguanidine is also described as a dihydrofolate reductase (DHFR) inhibitor.
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| ln Vitro |
In vitro, sulfaguanidine has been studied extensively for its antibacterial properties against various bacteria, including Gram-positive and Gram-negative strains such as Escherichia coli, Staphylococcus aureus, and Streptococcus pneumoniae. It is effective against Gram-negative enteric bacteria. Its antibacterial activity has been confirmed in numerous studies.
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| ln Vivo |
In rats, sulfaguanidine (2.5 mg/kg; IV) displays the following characteristics: Vdss (0.65 in adults, Neonatal 0.59 L/kg), AUC0-∞ (8.18 in adults, and 0.14 L/h/kg in neonates), and CLt (0.29 in adults, 0.14 L/h/kg in neonates) [3]. In rats, sulfaguanidine (2.5 mg/kg; oral) has the following characteristics: Tmax (1.67 in adults, newborns), Cmax (0.41 in adults, 3.56 μg/mL in neonates), and absolute bioavailability (12.76% in adults, 57.86% in neonates). 1.50 hours)[2].
Sulfaguanidine has been used for the treatment of intestinal infections in vivo. It is a sulfonamide antibiotic that has been used since the 1940s for bacterial infections. As an orally active agent, it is effective in the gastrointestinal tract, where it inhibits the synthesis of nutritional factors by intestinal bacteria. |
| Enzyme Assay |
The antibacterial activity of sulfaguanidine can be assessed using standard antimicrobial susceptibility testing methods, such as broth microdilution or agar diffusion assays. The minimum inhibitory concentration (MIC) against various bacterial strains is determined by incubating bacteria with serial dilutions of the compound and observing growth inhibition. The MIC values are used to quantify the compound's antibacterial potency.
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| Cell Assay |
Cellular assays for sulfaguanidine involve treating bacterial cultures with the compound and measuring bacterial growth over time. The optical density of the culture is monitored, and the growth inhibition is calculated. The effects on folic acid synthesis can be assessed by measuring the levels of folate intermediates in bacterial cells. The compound's activity against various Gram-positive and Gram-negative bacteria is evaluated.
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| Animal Protocol |
In vivo efficacy of sulfaguanidine is typically evaluated in animal models of intestinal infection, such as mouse models of bacillary dysentery. Animals are infected with pathogenic bacteria and then treated with sulfaguanidine via oral administration. The survival rate, bacterial load in the intestines, and clinical signs of infection are monitored.
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| ADME/Pharmacokinetics |
Sulfaguanidine has a molecular weight of 214.24 and a formula of C7H10N4O2S. It is a white to off-white crystalline powder with a melting point of 190-193°C. Its solubility in water is 0.805 mg/mL, and it is slightly soluble in ethanol.
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| Toxicity/Toxicokinetics |
Sulfaguanidine, like other sulfonamides, can cause adverse effects such as hypersensitivity reactions, crystalluria, and hematological disorders. Its use has declined with the availability of newer antibiotics. Specific toxicity data, such as LD50 values, are not detailed in the available literature, but it is considered to have a manageable safety profile when used appropriately.
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| References |
[1]. LOWELL A, et, al. THE USE OF SULFAGUANIDINE IN THE TREATMENT OF DYSENTERY CARRIERS. JAMA. 1942 Apr; 118(15):1268-1271.
[2]. Mizuno N, et, al. Gastrointestinal absorption of sulfaguanidine in neonatal and adult rats. J Pharmacobiodyn. 1986 Oct;9(10):787-92. |
| Additional Infomation |
Sulfaguanidine is a guanidine-containing sulfonamide drug used to block folic acid synthesis; it is primarily used in veterinary medicine. It has anti-infective properties. Sulfaguanidine is a guanidine derivative of sulfonamides and is used in veterinary medicine. Sulfaguanidine is poorly absorbed in the intestines but is well-suited for treating bacterial dysentery and other intestinal infections. It is a sulfonamide antibacterial drug used to treat intestinal infections.
Sulfaguanidine is a sulfonamide antibiotic that has been used for the treatment of enteric infections. It is one of the earliest sulfonamides used for intestinal infections. Its use has largely been replaced by newer antibiotics, but it remains a reference compound in antibacterial research. It is not a commonly used drug in modern clinical practice. |
| Molecular Formula |
C7H10N4O2S
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|---|---|
| Molecular Weight |
214.2449
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| Exact Mass |
214.052
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| CAS # |
57-67-0
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| Related CAS # |
Sulfaguanidine-13C6;Sulfaguanidine-d4
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| PubChem CID |
5324
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
426.1±47.0 °C at 760 mmHg
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| Melting Point |
190-193°C
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| Flash Point |
211.5±29.3 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.695
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| LogP |
-1.22
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| Hydrogen Bond Donor Count |
3
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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 |
307
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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=C(\N([H])[H])/N([H])[H])(=O)=O
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| InChi Key |
BRBKOPJOKNSWSG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H10N4O2S/c8-5-1-3-6(4-2-5)14(12,13)11-7(9)10/h1-4H,8H2,(H4,9,10,11)
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| Chemical Name |
2-(4-aminophenyl)sulfonylguanidine
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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 (~466.77 mM)
H2O : ~3.33 mg/mL (~15.54 mM) |
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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% 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 (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 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 (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. |
| 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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