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:

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
• General Description: Sulfamethizole is a sulfonamide-derived antibacterial agent that can act as a ligand in coordination chemistry, forming stable complexes with metal ions such as copper(II), cobalt(II), nickel(II), and zinc(II). These complexes exhibit distinct coordination geometries, as demonstrated by X-ray crystallography, highlighting sulfamethizole's ability to bind metals through its sulfonamide and thiadiazole functional groups. This property may influence its pharmacological behavior or potential applications in metal-based drug development.

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-(2,6-diamino-pyridin-3-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

N,N'-bis-(5-methyl-[1,3,4]thiadiazol-2-yl)-4,4'-(2,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,4-diyldiamino)-bis-benzenesulfonamide

Refernces

Coordination chemistry of sulfamethizole: Crystal structures of [Cu(sulfamethizolate)₂(py)₂(OH₂)]·H₂O, [M(sulfamethizolate)₂(py)₂(OH₂)₂] [M = Co and Ni] and {Cu(sulfamethizolate)₂(dmf)₂}(∞)

10.1016/S0277-5387(00)00474-5

This research focuses on the coordination chemistry of sulfamethizole, an antibacterial drug, with various metal ions. The study aims to synthesize and characterize copper, cobalt, nickel, and zinc complexes of sulfamethizole, and to determine their crystal structures for the first time. The researchers used sulfamethizole (Hsmtz) as the ligand and synthesized complexes with copper (II), cobalt (II), nickel (II), and zinc (II) ions using reagents such as CuSO4·5H2O, CoCl2·6H2O, NiCl2·6H2O, and ZnCl2·2H2O. The crystal structures were determined using X-ray diffraction, revealing different coordination geometries for the metal ions in these complexes.

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