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)
• description: Sulfadiazine is an oral sulfonamide anti-bacterial agent. it is a synthetic pyrimidinyl sulfonamide derivative, The chemical classification of sulfadiazine is Sulfonamides.The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus. Sulfadiazine is used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.
• Indications: Sulfa drugs belong to broad-spectrum antibiotic. However, because of the resistance of many current clinical common pathogens to this class of drugs, it is only used for treating the infection caused by sensitive bacteria and other kinds of susceptible pathogens. Sulfadiazine (not including the FDC of this drug together with trimethoprim) has its main indications as follows: 1. Used for prevention and treating the meningococcal meningitis caused by sensitive Meningococcal. 2. When being used in combination with trimethoprim, it can be used for treating the otitis media and other kinds of soft tissue infection caused sensitive Haemophilus influenzae, Streptococcus pneumoniae and other kinds of Streptococcus. 3. Used for treating disease related to star nocardia. 4. Used as the adjuvant drug assisting in the treatment of chloroquine-resistant falciparum malaria. 5. Used as the secondary-choice drug for treatment of Chlamydia trachomatis-induced urethritis and cervicitis. 6. Used as the secondary-choice drug for treatment of neonatal inclusion conjunctivitis caused by Chlamydia trachomatis.
• Uses: It is excellent kinds of sulfa drugs with strong antibacterial activity, good efficacy, rapid absorption, slow excretion rate and high plasma concentration. It is clinically used for treating upper respiratory tract infection, Meningococcal meningitis, otitis media, boils carbuncle, puerperal fever, urinary tract infections and acute dysentery and so on. It is a sulfa-type drug which is used for the treatment of infection caused by hemolytic streptococcus, pneumococcus, meningococcis, Neisseria gonorrhea, and E. coli. It is a sulfa drug with antibacterial effect and convergence effect. It is used in the form of silver salts (sulfadiazine silver) as an external antibacterial agent, primarily for treating burns. It is believed that the presence of the silver ion in the molecule facilitates increased antimicrobial and wound-healing action. Sulfonamide antibacterial. DMSO soluble potent immunosuppressant, neuroprotective neuroregenerative, in vitro T cell proliferation blocker. disrupts calcineurin-mediated signal transduction in T lymphocytes
• Therapeutic Function: Antibacterial
• Clinical Use: Urinary tract infection Nocardiasis Chancroid Toxoplasmosis (in combination with pyrimethamine) Meningococcal infections Prophylaxis of rheumatic fever
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of crystalluria with methenamine. Anticoagulants: effect of coumarins enhanced; metabolism of phenindione possibly inhibited. Antiepileptics: antifolate effect and concentration of phenytoin increased. Antimalarials: increased risk of antifolate effect with pyrimethamine. Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis). Ciclosporin: reduced levels of ciclosporin; increased risk of nephrotoxicity. Cytotoxics: increase risk of methotrexate toxicity

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-(2-bromo-propionyl)-sulfanilic acid pyrimidin-2-ylamide

N-dichloroacetyl-sulfanilic acid pyrimidin-2-ylamide

Refernces

• 1、 -. "Synthesis method of sulfadiazine". Paragraph 0017-0032. . Retrieved 2021/03/13.
• 2、 -. "Green synthesis method of sulfadiazine". Paragraph 0013; 0017; 0020-0027. . Retrieved 2020/07/02.