Sulfamethoxazole

  • #LGM Pharma is a Sulfamethoxazole CAS# 723-46-6 API supplier distributor based in the USA. Inquire about DMF, cGMP, price, availability, delivery, purity, and more.
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  • #LGM Pharma offers this active ingredient but not the finished dosage forms.

Product Details:

  • CAS No: 723-46-6
  • AHFC code: 08:12.2
  • Synonyms: 3-(p-Aminophenylsulfonamido)-5-methylisoxazole, 3-Sulfanilamido-5-methylisoxazole, 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide, Gantanol (tn), SMX, Sulfamethoxazole
  • ATC Code: J01EC01
  • Chemical Formula: C51H40N6O23S6
  • Molecular Weight: 253.278
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01015 (APRD00076)
  • SMILES: CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
  • InChl: JLKIGFTWXXRPMT-UHFFFAOYSA-N
  • PubChem: 5329
  • IUPAC: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide

Additional Details

Indication:
For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
Pharmacodynamics:
Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethoxazole is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA. Sulfamethoxazole is normally given in combination with Trimethoprim, a dihydrofolate reductase inhibitor, which inhibits the reduction of dihydrofolic acid to tetrahydrofolic acid. Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone.
Mode of Action:
Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
Metabolism:
Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.
Toxicity:
Sulfamethoxazole may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
General Reference:
Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1). Any patent infringement and resulting liability is solely at buyer risk.

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