Product Name

Sulfamethoxazole

CAS Number

723-46-6

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Product Name:
Sulfamethoxazole
CAS Number:
723-46-6
Indication:
For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
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.

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.

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.

IUPAC:
4-amino-N-(5-methyl-1, 2-oxazol-3-yl)benzene-1-sulfonamide
ATC:
J01EC01
PubChem:
5329
DrugBank:
DB01015 (APRD00076)
Formula:
C51H40N6O23S6
Molecular Mass:
253.278
Synonyms:
3-(p-Aminophenylsulfonamido)-5-methylisoxazole, 3-Sulfanilamido-5-methylisoxazole, 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide, Gantanol (tn), SMX, Sulfamethoxazole
SMILES:
CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
AHFS Code:
08:12.2
InChi:
JLKIGFTWXXRPMT-UHFFFAOYSA-N

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