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Sulfamethazine

Catalog No. DB01582 Name DrugBank
CAS Number 57-68-1 Website http://www.ualberta.ca/
M. F. C12H14N4O2S Telephone (780) 492-3111
M. W. 278.33016 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1362

SYNONYMS

IUPAC name
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide
IUPAC Traditional name
sulfamethazine

DATABASE IDS

PubChem SID 46507146
CAS Number 57-68-1
PubChem CID 5327

PROPERTIES

Hydrophobicity(logP) 0.89 [BIOBYTE (1995)]
Solubility 1.5 mg/mL at 29 oC [MERCK INDEX (1983); at pH 7]

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides. [PubChem]
Indication For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
Pharmacology 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 DNA.
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.
Absorption Rapidly absorbed following oral administration.

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