SULFAMETHIZOLE

Base Information

• Chemical Name: SULFAMETHIZOLE
• CAS No.: 144-82-1
• Molecular Formula: C9H10 N4 O2 S2
• Molecular Weight: 270.336
• Hs Code.: 2935904000
• European Community (EC) Number: 205-641-1
• NSC Number: 757327
• UNII: 25W8454H16
• DSSTox Substance ID: DTXSID5023615
• Nikkaji Number: J4.419I
• Wikipedia: Sulfamethizole
• Wikidata: Q3976824
• NCI Thesaurus Code: C47736
• Metabolomics Workbench ID: 42908
• ChEMBL ID: CHEMBL1191
• Mol file: 144-82-1.mol

Synonyms:Sulfanilamide,N1-(5-methyl-1,3,4-thiadiazol-2-yl)- (6CI,7CI,8CI); 2-Methyl-5-sulfanilamido-1,3,4-thiadiazole;2-Sulfanilamido-5-methyl-1,3,4-thiadiazole;4-Amino-N-(5-methyl-[1,3,4]thiadiazol-2-yl)benzenesulfonamide;5-Methyl-2-sulfanilamido-1,3,4-thiadiazole; Ayerlucil; Famet; Lucosil;Methazol; Microsul; N-(5-Methyl-1,3,4-thiadiazol-2-yl)-4-aminobenzenesulfonamide;N1-(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanilamide; Renasul; Rufol; Salimol;Sulfamethiazole; Sulfamethizol; Sulfamethizole; Sulfamethylthiadiazole;Sulfapyelon; Sulfstat; Sulfurine; Sulphamethizole; Tetracid; Thidicur;Thiosulfil; Thiosulfil Forte; Ultrasul; Urocydal; Urodiaton; Urolucosil;Urosulfin; VK 53

Chemical Property of SULFAMETHIZOLE

Chemical Property:

• Appearance/Colour: white to pale yellow crystalline powder
• Vapor Pressure: 2.56E-10mmHg at 25°C
• Melting Point: 208 - 210 C
• Refractive Index: 1.6440 (estimate)
• Boiling Point: 504.9°Cat760mmHg
• PKA: 5.45(at 25℃)
• Flash Point: 259.1°C
• PSA: 134.59000
• Density: 1.562g/cm³
• LogP: 2.96450
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 529mg/L(20 oC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 270.02451792
• Heavy Atom Count: 17
• Complexity: 349

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sulfamethizole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NN=C(S1)NS(=O)(=O)C2=CC=C(C=C2)N
• Recent EU Clinical Trials: Short course antibiotic treatment of Gram-negative bacteremia: A multicenter, randomized, non-blinded, non-inferiority interventional study
• Description: Sulfamethizole is a broad spectrum sulfonamide antibiotic (MIC90s = 1.25-5,000 μg/ml against clinical isolates of E. coli and K. pneumoniae). It inhibits dihydropteroate synthase, an enzyme involved in folate biosynthesis. Formulations containing sulfamethizole have previously been used to treat urinary tract infections.
• Uses: This drug has antibacterial activity with respect to streptococci, pneumococci, staphylococci, meningococci, gonococci, colon bacillus, pathogenic dysentery, and others. It is not very toxic. It is generally used for acute, uncomplicated infections of the urinary tract that are caused by sensitive organisms. Because it is removed quickly from the organism by the kidneys, the level of drug in the plasma remains low, and therefore it is not used for treating infections that are localized in the urinary tract. Sulfisoxazole is the more preferred drug. Synonyms of this drug are urosol, rufol, thiosulfil, and others. Sulfonamide antibacterial. Sulfamethizole is a sulfonamide based antibiotic that exhibit bactericidal activities towards gram-negative bacteria. Sulfamehizole was shown to be effective in treating gram-negative Bacillus AmpC en zyme in elderly patients with lower respiratory tract infection and as well as against microbs responsible for tuberculosis.
• Therapeutic Function: Antibacterial

Technology Process of SULFAMETHIZOLE

There total 9 articles about SULFAMETHIZOLE 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: 100.0%

N-(5-methyl-1,3,4-thiadiazol-2-yl)-4-nitrobenzenesulfonamide (349621-24-5) → sulfamethizole (144-82-1)

Guidance literature:

With hydrogenchloride; iron; In ethanol; water; for 3h; Reflux;

Reference yield: 72.0%

N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide (39719-87-4) → sulfamethizole (144-82-1)

Guidance literature:

N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide; With hydrogenchloride; In water; for 0.5h; Reflux;

With sodium carbonate; In water;

DOI:10.1016/j.bmc.2011.01.049

Reference yield:

p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfamethizole (144-82-1)

Guidance literature:

Multi-step reaction with 2 steps

2: aqueous HCl

With hydrogenchloride;

DOI:10.1002/ardp.19512840202

upstream raw materials:

5-methyl-1,3,4-thiadiazol-2-amine

4-Nitrobenzenesulfonyl chloride

p-acetylaminobenzenesulfonyl chloride

N-(4-(N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)acetamide

Downstream raw materials:

sulfanilic acid-(3,5-dimethyl-3H-[1,3,4]thiadiazol-2-ylidenamide)

4-(8-hydroxy-quinolin-5-ylazo)-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-benzenesulfonamide

4-oxo-4H-chromene-2-carboxylic acid 4-(5-methyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-anilide

[(sulphamethizole)Ag]NO3

Refernces

• 1、 -. "MODULATORS OF IMMUNOINHIBITORY RECEPTOR PD-1, AND METHODS OF USE THEREOF". . . Retrieved 2011/07/30.
• 2、 -. "Process for formulating a synthetic drug for use in animal feed, and resulting formulation". . . Retrieved 2008/06/13.