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QuickView for sulfamethazine (compound)

Name: Sulfamethazine
PubChem Compound ID: 5327
Description: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.
Molecular formula: C12H14N4O2S
Molecular weight: 278.331 g/mol
Vertolan; Sulfanilamide, N1-(4,6-dimethyl-2-pyrimidinyl)-; CBDivE_012932; Diazyl (VAN); [(4-Aminophenyl)sulfonyl](4,6-dimethylpyrimidin-2-yl)amine; Sulfisomidine; Sulfanilamide, N(sup1)-(2,6-dimethyl-4-pyrimidinyl)-; CCRIS 3701; Sulfadimidinum [INN-Latin]; 4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide.
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Name: Sulfamethazine
Name (isomeric): DB01582
Drug Type: small molecule
Description: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.
Category: Anti-Infective Agents, Sulfonamides
CAS number: 57-68-1
Indication: For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
Sulfamethazine 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). Sulfamethazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and D...
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Mechanism 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. Pyr...
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Absorption: Rapidly absorbed following oral administration.
Toxicity: Sulfamethazine 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.
Food interaction:
Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
Drug interaction:
CyclosporineThe sulfonamide decreases the effect of cyclosporine
ChlorpropamideSulfonamide/sulfonylurea: possible hypoglycemia
MethotrexateThe sulfamide increases the toxicity of methotrexate