S0383

Sulfameter

• Synonym(s): 5-Methoxysulfadiazine, N¹-(5-Methoxypyrimidin-2-yl)sulfanilamide, Sulfamethoxydiazine
• Empirical Formula (Hill Notation): C₁₁H₁₂N₄O₃S
• CAS Number: 651-06-9
• Molecular Weight: 280.30
• Beilstein/REAXYS Number: 621130
• EC Number: 211-480-8
• MDL number: MFCD00006067
• UNSPSC Code: 51283913
• PubChem Substance ID: 24899422
• NACRES: NA.85

Properties

• form: powder
• Quality Level: 200
• storage condition: (Keep container tightly closed in a dry and well-ventilated place. Light sensitive.)
• color: white to faint yellow
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria; mycobacteria; parasites
• mode of action: enzyme | inhibits
• storage temp.: 2-8°C
• SMILES string: COc1cnc(NS(=O)(=O)c2ccc(N)cc2)nc1
• InChI: 1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
• InChI key: GPTONYMQFTZPKC-UHFFFAOYSA-N

Description

General description

Chemical structure: sulfonamide

Application

Sulfameter is a sulfonamide antibiotic used as a leprostatic agent and to treat urinary tract infections[1]. It has been investigated as a potential therapy for chloroquine-resistant malaria during pregnancy[2].

Biochem/physiol Actions

Sulfameter is a sulfonamide antibiotic. Sulfonamides block the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfonamides are competitive inhibitors of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid[3]. Sulfameter is a dihydrofolate reductase (DHFR) inhibitor. Sulfonamides are active against Gram positive bacteria and Gram negative bacteria. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Light sensitive.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves