Tìm theo
Sulfadiazine
Các tên gọi khác (12 ) :
  • 2-sulfanilamidopyrimidine
  • 2-sulfanilylaminopyrimidine
  • 4-amino-N-2-pyrimidinylbenzenesulfonamide
  • N(1)-2-Pyrimidinylsulfanilamide
  • N(1)-2-Pyrimidylsulfanilamide
  • N1-2-pyrimidinylsulfanilamide
  • N1-2-pyrimidylsulfanilamide
  • Sulfadiazina
  • Sulfadiazine
  • Sulfadiazinum
  • Sulfapyrimidine
  • Sulphadiazine
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 68-35-9
ATC: D06BA01, J01EC02
ĐG : Amend
CTHH: C10H10N4O2S
PTK: 250.277
One of the short-acting sulfonamides used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C10H10N4O2S
Phân tử khối
250.277
Monoisotopic mass
250.052446274
InChI
InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
InChI Key
InChIKey=SEEPANYCNGTZFQ-UHFFFAOYSA-N
IUPAC Name
4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide
Traditional IUPAC Name
sulfadiazine
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1
Độ tan chảy
255.5 dec °C
Độ hòa tan
77 mg/L (at 25 °C)
logP
-0.09
logS
-3.51
pKa (strongest acidic)
6.99
pKa (Strongest Basic)
2.01
PSA
97.97 Å2
Refractivity
64.2 m3·mol-1
Polarizability
24.39 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
5
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
6.36
Dược Lực Học : Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Cơ Chế Tác Dụng : One of the short-acting sulfonamides used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections. [PubChem] Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Dược Động Học :

▧ Route of Elimination :
Sulfadiazine is excreted largely in the urine.
Độc Tính : Oral LD50 in mouse is 1500 mg/kg.
Chỉ Định : For the treatment of rheumatic fever and meningococcal meningitis
Tương Tác Thuốc :
  • Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
  • Cyclosporine The sulfonamide decreases the effect of cyclosporine
  • Fosphenytoin The sulfonamide increases the effect of hydantoin
  • Methenamine mandelate Possible crystallization of urates with this combination
  • Methotrexate The sulfamide increases the toxicity of methotrexate
  • Phenytoin The sulfonamide increases the effect of hydantoin
  • Tamoxifen Sulfadiazine may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfadiazine is initiated, discontinued or dose changed.
  • Tolbutamide Tolbutamide and Sulfadiazine are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed.
  • Torasemide Sulfadiazine, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Sulfadiazine is initiated, discontinued or dose changed.
  • Trimethoprim The strong CYP2C9 inhibitor, Sulfadiazine, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Sulfadiazine is initiated, discontinued or dose changed.
  • Warfarin Sulfadiazine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if sulfadiazine is initiated, discontinued or dose changed.
  • Zafirlukast Sulfadiazine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if sulfadiazine is initiated, discontinued or dose changed.
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Adiazine
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00359
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5215
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506164
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07658
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00587
ChemSpider
http://www.chemspider.com/Chemical-Structure.5026.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0185-0757-10
PharmGKB
http://www.pharmgkb.org/drug/PA451539
Wikipedia
http://en.wikipedia.org/wiki/Sulfadiazine
Drugs.com
http://www.drugs.com/cdi/sulfadiazine.html
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