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药品详细

Sulfamethazine(磺胺二甲嘧啶)

化学结构式图
中文名
磺胺二甲嘧啶
英文名
Sulfamethazine
分子式
C12H14N4O2S
化学名
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide
分子量
Average: 278.33
Monoisotopic: 278.083746402
CAS号
57-68-1
ATC分类
J01E 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides. [PubChem]

生产厂家
    封装厂家
    参考
    Synthesis Reference Not Available
    General Reference Not Available
    剂型
    规格
    化合物类型
    Type small molecule
    Classes
    • Benzenesulfonamides
    • Sulfanilamides
    Substructures
    • Sulfonyls
    • Aliphatic and Aryl Amines
    • Benzene and Derivatives
    • Benzenesulfonamides
    • Pyrimidines and Derivatives
    • Heterocyclic compounds
    • Aromatic compounds
    • Sulfanilamides
    • Sulfonamides
    • Imines
    • Cyanamides
    • Anilines
    适应症
    药理
    Indication For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
    Pharmacodynamics 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.
    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. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
    Absorption Rapidly absorbed following oral administration.
    Volume of distribution Not Available
    Protein binding Not Available
    Metabolism
    Not Available
    Route of elimination Not Available
    Half life Not Available
    Clearance Not Available
    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.
    Affected organisms Not Available
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 198.5 °C PhysProp
    water solubility 1500 mg/L (at 29 °C) MERCK INDEX (1983); at pH 7
    logP 0.89 BIOBYTE (1995)
    pKa 7.59 SANGSTER (1994)
    Predicted Properties
    Property Value Source
    water solubility 2.30e-01 g/l ALOGPS
    logP 0.43 ALOGPS
    logP 0.65 ChemAxon
    logS -3.1 ALOGPS
    pKa (strongest acidic) 6.99 ChemAxon
    pKa (strongest basic) 2.04 ChemAxon
    physiological charge -1 ChemAxon
    hydrogen acceptor count 5 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 97.97 ChemAxon
    rotatable bond count 2 ChemAxon
    refractivity 73.38 ChemAxon
    polarizability 28.8 ChemAxon
    药物相互作用
    Drug Interaction
    Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
    Cyclosporine The sulfonamide decreases the effect of cyclosporine
    Methotrexate The sulfamide increases the toxicity of methotrexate
    食物相互作用
    • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.

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