Tìm theo
Sulfamethoxazole
Các tên gọi khác (6 ) :
  • 3-(p-Aminophenylsulfonamido)-5-methylisoxazole
  • 3-Sulfanilamido-5-methylisoxazole
  • 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
  • Gantanol (tn)
  • SMX
  • Sulfamethoxazole
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 723-46-6
ATC: J01EC01
ĐG : Medisca Inc. , http://www.medisca.com
CTHH: C10H11N3O3S
PTK: 253.278
A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C10H11N3O3S
Phân tử khối
253.278
Monoisotopic mass
253.052111923
InChI
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChI Key
InChIKey=JLKIGFTWXXRPMT-UHFFFAOYSA-N
IUPAC Name
4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
Traditional IUPAC Name
sulfamethoxazole
SMILES
CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
Độ tan chảy
167 °C
Độ hòa tan
610 mg/L (at 37 °C)
logP
0.89
logS
-2.62
pKa (strongest acidic)
6.16
pKa (Strongest Basic)
1.97
PSA
98.22 Å2
Refractivity
64.5 m3·mol-1
Polarizability
24.99 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
4
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208) 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.
Dược Động Học :
▧ Absorption :
Rapidly absorbed following oral administration. Also well-absorbed topically.
▧ Protein binding :
70%
▧ Metabolism :
Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.
▧ Half Life :
10 hours
Độc Tính : 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.
Chỉ Định : For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
Tương Tác Thuốc :
  • Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
  • Cyclosporine The sulfonamide decreases the effect of cyclosporine
  • Methotrexate The sulfamide increases the toxicity of methotrexate
  • Pralatrexate Decreases renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects.
  • Tobramycin Increased risk of nephrotoxicity
  • Tolbutamide Tolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Sulfamethoxazole. Consider alternate therapy or monitor for changes in Sulfamethoxazole therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
  • Warfarin Sulfamethoxazole may increase the anticoagulant effect of warfarin by decreasing its metabolism. Consider alternate therapy or monitor for changes in prothrombin time if sulfamethoxazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Gantanol
  • Công ty :
    Sản phẩm biệt dược : Sinomin
  • Công ty :
    Sản phẩm biệt dược : Urobak
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01015
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5329
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508111
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07315
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00447
ChemSpider
http://www.chemspider.com/Chemical-Structure.5138.html
PharmGKB
http://www.pharmgkb.org/drug/PA451544
Wikipedia
http://en.wikipedia.org/wiki/Sulfamethoxazole
RxList
http://www.rxlist.com/cgi/generic3/gantanol.htm
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