Sulfadiazine

Base Information

• Chemical Name: Sulfadiazine
• CAS No.: 68-35-9
• Deprecated CAS: 141582-64-1
• Molecular Formula: C10H10N4O2S
• Molecular Weight: 250.281
• Hs Code.: 29335990
• European Community (EC) Number: 200-685-8
• NSC Number: 757324,35600
• UNII: 0N7609K889
• DSSTox Substance ID: DTXSID7044130
• Nikkaji Number: J1.418D
• Wikipedia: Sulfadiazine
• Wikidata: Q2555060
• NCI Thesaurus Code: C29468
• RXCUI: 10171
• Metabolomics Workbench ID: 42733
• ChEMBL ID: CHEMBL439
• Mol file: 68-35-9.mol

Synonyms:Sulfadiazine;Sulfadiazine, Zinc;Sulfazin;Sulfazine;Sulphadiazine;Zinc Sulfadiazine

Chemical Property of Sulfadiazine

Chemical Property:

• Appearance/Colour: White to slightly yellow crystalline powder
• Melting Point: 254 °C
• Refractive Index: 1.679
• Boiling Point: 512.6 °C at 760 mmHg
• PKA: pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
• Flash Point: 263.8 °C
• PSA: 106.35000
• Density: 1.496 g/cm³
• LogP: 2.59460
• Storage Temp.: 0-6°C
• Solubility.: Soluble in dimethyl sulfoxide.
• Water Solubility.: 67.13mg/L(25 oC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 250.05244675
• Heavy Atom Count: 17
• Complexity: 327

Purity/Quality:

99% ^*data from raw suppliers

Sulfadiazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-42/43-43-42
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
• Recent ClinicalTrials: StrataXRT for the Prevention and Treatment of Radiation Dermatitis in Breast Cancer or Head and Neck Cancer Patients
• Recent EU Clinical Trials: Evaluation of phage therapy for the treatment of Pseudomonas aeruginosa wound infections in burned patients (Phase I-II clinical trial)
• General Description: Sulfadiazine is a sulfonamide antibiotic that inhibits bacterial growth by competitively antagonizing para-aminobenzoic acid (PABA), thereby disrupting folic acid synthesis. It is effective against a broad spectrum of Gram-positive and Gram-negative bacteria, as well as some protozoa, and is commonly used to treat infections such as urinary tract infections, toxoplasmosis, and meningitis. Sulfadiazine is often administered in combination with pyrimethamine for enhanced efficacy against Toxoplasma gondii. While generally well-tolerated, it may cause adverse effects such as crystalluria, hypersensitivity reactions, and hematologic disturbances. Its use has declined with the advent of newer antibiotics, but it remains a valuable therapeutic option in specific clinical contexts.

Technology Process of Sulfadiazine

There total 23 articles about Sulfadiazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

2-aminopyrimidine (109-12-6) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfadiazine (68-35-9)

Guidance literature:

2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride; With calcium carbonate; In toluene; at 20 - 65 ℃;

With water; sodium hydroxide; In toluene; at 100 - 115 ℃;

With acetic acid; pH=5 - 5.5; Reagent/catalyst;

Reference yield: 98.0%

N-benzylidene-sulfanilic acid pyrimidin-2-ylamide (77218-33-8) → sulfadiazine (68-35-9)

Guidance literature:

With water; In acetone; at 20 ℃; for 0.666667h; Irradiation;

DOI:10.1246/cl.2001.708

Reference yield: 91.0%

4-amino-N-(diaminomethylene) benzenesulfonamide (57-67-0) + 3-ethoxyacrolein (19060-08-3) → sulfadiazine (68-35-9)

Guidance literature:

In ethanol; at 100 ℃; for 4h; Green chemistry;

upstream raw materials:

2-aminopyrimidine

3-(4-acetylamino-benzenesulfonyl)-2-benzenesulfonylimino-2,3-dihydro-thiazole

2-chloropyrimidine

sulfanilamide

Downstream raw materials:

4-amino-N-methyl-N-(pyrimidin-2-yl)benzene-1-sulfonamide

N-(4-pyrimidin-2-ylsulfamoyl-phenyl)-succinamic acid

N-pyrimidin-2-yl-4-[(2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzenesulfonamide

4-[(2-oxo-benzooxazol-3-ylmethyl)-amino]-N-pyrimidin-2-yl-benzenesulfonamide

Refernces

10.1021/jo00907a012

The research investigates the scope and limitations of the dimethyl sulfoxide-trifluoroacetic anhydride (DMSO-TFAA) reagent for the preparation of iminosulfuranes. The study aims to explore the efficiency and applicability of this reagent with various nitrogen-containing compounds, including aryl amines, amides, sulfonamides, and urea. The key chemicals used in the research are DMSO and TFAA, which form an intermediate reagent that reacts with the nitrogen compounds to produce iminosulfuranes. The research concludes that the DMSO-TFAA reagent is highly effective, yielding iminosulfuranes in 40-90% yields, and is particularly reactive even with aromatic amines containing certain ortho substituents. The study also highlights the reagent's ability to form iminosulfuranes from previously uncharacterized compounds like sulfanilamide and sulfadiazine. However, it notes limitations with relatively basic amines and certain aromatic compounds. The findings suggest that the DMSO-TFAA reagent is a valuable tool for the preparation of iminosulfuranes, offering a more efficient and versatile alternative to other activated DMSO reagents.