Sulfadiazine sodium
Overview
Description
Sulfadiazine sodium is a sulfonamide antibiotic used to treat a variety of bacterial infections. It is particularly effective against urinary tract infections, trachoma, and chancroid . This compound is also used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections .
Scientific Research Applications
Sulfadiazine sodium has a wide range of scientific research applications:
Chemistry: It is used in the synthesis of various chemical compounds and as a reagent in analytical chemistry.
Biology: This compound is used to study the effects of antibiotics on bacterial growth and resistance.
Medicine: It is used to treat bacterial infections and as a part of combination therapy for toxoplasmosis.
Mechanism of Action
Target of Action
Sulfadiazine sodium primarily targets the bacterial enzyme dihydropteroate synthetase . This enzyme plays a crucial role in the synthesis of folic acid, which is essential for bacterial growth and survival .
Mode of Action
This compound acts as a competitive inhibitor of dihydropteroate synthetase . By binding to this enzyme, it prevents the proper processing of para-aminobenzoic acid (PABA), a precursor required for folic acid synthesis . This inhibition disrupts the synthesis of folic acid, thereby inhibiting bacterial growth .
Biochemical Pathways
The primary biochemical pathway affected by this compound is the folic acid synthesis pathway in bacteria . By inhibiting dihydropteroate synthetase, this compound disrupts this pathway, leading to a deficiency in folic acid. Since folic acid is necessary for the synthesis of nucleic acids and proteins, its deficiency impairs bacterial growth and proliferation .
Pharmacokinetics
They are known to bind to plasma proteins and are metabolized in the liver . The metabolites and unchanged drug are primarily excreted in the urine .
Result of Action
The molecular effect of this compound’s action is the inhibition of folic acid synthesis, which leads to a deficiency in folic acid within the bacterial cell . On a cellular level, this results in impaired synthesis of nucleic acids and proteins, leading to inhibited bacterial growth and proliferation .
Action Environment
Environmental factors can influence the action of this compound. For instance, the presence of organic matter, such as humic acid, in the soil can affect the sorption and transport of sulfadiazine, thereby influencing its environmental fate and eco-toxicity . Furthermore, the pH and ionic strength of the solution can affect the sorption of sulfadiazine on humic acid . These factors can potentially influence the efficacy and stability of this compound in the environment .
Biochemical Analysis
Biochemical Properties
Sulfadiazine sodium plays a significant role in biochemical reactions. It interacts with various enzymes, proteins, and other biomolecules. For instance, it forms inclusion compounds with β-cyclodextrin and its derivatives . These interactions have been confirmed through isothermal titration calorimetry and nuclear magnetic resonance experiments .
Cellular Effects
The effects of this compound on various types of cells and cellular processes are profound. It influences cell function, including impacts on cell signaling pathways, gene expression, and cellular metabolism. For instance, the inclusion compounds of this compound with β-cyclodextrin and its derivatives have shown increased efficiency against Staphylococcus aureus and Pseudomonas aeruginosa compared to the free this compound molecule .
Preparation Methods
Synthetic Routes and Reaction Conditions
Sulfadiazine sodium is synthesized by the diazotization of the primary amine group of sulfadiazine with sodium nitrite and hydrochloric acid, followed by coupling with γ-resorsolic acid in an alkaline medium of sodium hydroxide . The compound is then purified and crystallized to obtain the final product.
Industrial Production Methods
In industrial settings, this compound is produced by adding sulfadiazine, trimethoprim, and enrofloxacin to a mixture of polyethylene glycol and propylene glycol, followed by heating and stirring . The solution is then standardized, and the pH is adjusted to 10.5-11 to obtain the final product .
Chemical Reactions Analysis
Types of Reactions
Sulfadiazine sodium undergoes various chemical reactions, including:
Oxidation: This compound can be oxidized by reactive oxidative species such as hydroxyl radicals and sulfate radicals.
Reduction: The compound can be reduced under specific conditions, although this is less common.
Substitution: this compound can undergo substitution reactions, particularly in the presence of strong nucleophiles.
Common Reagents and Conditions
Oxidation: Common reagents include potassium monopersulfate (Oxone) and UV light.
Substitution: Strong nucleophiles such as sodium hydroxide are often used.
Major Products
The major products formed from these reactions include various oxidized and substituted derivatives of this compound, which can have different pharmacological properties .
Comparison with Similar Compounds
Sulfadiazine sodium is part of the sulfonamide class of antibiotics, which includes other compounds such as sulfamethoxazole and sulfisoxazole . Compared to these similar compounds, this compound has a broader spectrum of activity and is more effective against certain types of bacteria . Additionally, it is often used in combination with other drugs, such as pyrimethamine, to enhance its effectiveness .
List of Similar Compounds
- Sulfamethoxazole
- Sulfisoxazole
- Sulfapyridine
- Sulfacetamide
Properties
| { "Design of the Synthesis Pathway": "Sulfadiazine sodium can be synthesized by reacting sulfadiazine with sodium hydroxide.", "Starting Materials": [ "Sulfadiazine", "Sodium hydroxide" ], "Reaction": [ "Dissolve sulfadiazine in water", "Add sodium hydroxide to the solution", "Heat the mixture to 70-80°C for 30 minutes", "Cool the mixture and filter the precipitate", "Wash the precipitate with water and dry it to obtain sulfadiazine sodium" ] } | |
CAS No. |
547-32-0 |
Molecular Formula |
C10H10N4NaO2S |
Molecular Weight |
273.27 g/mol |
IUPAC Name |
sodium;(4-aminophenyl)sulfonyl-pyrimidin-2-ylazanide |
InChI |
InChI=1S/C10H10N4O2S.Na/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h1-7H,11H2,(H,12,13,14); |
InChI Key |
RKISJHYCSQKDTK-UHFFFAOYSA-N |
SMILES |
C1=CN=C(N=C1)[N-]S(=O)(=O)C2=CC=C(C=C2)N.[Na+] |
Canonical SMILES |
C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N.[Na] |
| 547-32-0 | |
Pictograms |
Irritant; Health Hazard |
Synonyms |
ulfadiazin-natrium |
Origin of Product |
United States |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Disclaimer and Information on In-Vitro Research Products
Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
