Tìm theo
Sulfisoxazole
Các tên gọi khác (32 ) :
  • 3,4-Dimethyl-5-sulfanilamidoisoxazole
  • 3,4-Dimethyl-5-sulfonamidoisoxazole
  • 3,4-Dimethyl-5-sulphanilamidoisoxazole
  • 3,4-Dimethyl-5-sulphonamidoisoxazole
  • 3,4-Dimethylisoxazole-5-sulfanilamide
  • 3,4-Dimethylisoxazole-5-sulphanilamide
  • 4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide
  • 4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulphonamide
  • 5-(4-Aminophenylsulfonamido)-3,4-dimethylisoxazole
  • 5-(P-Aminobenzenesulfonamido)-3,4-dimethylisoxazole
  • 5-(P-Aminobenzenesulphonamido)-3,4-dimethylisoxazole
  • 5-Sulfanilamido-3,4-dimethylisoxazole
  • 5-Sulphanilamido-3,4-dimethyl-isoxazole
  • N'-(3,4)dimethylisoxazol-5-yl-sulphanilamide
  • N(1)-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide
  • N(1)-(3,4-Dimethyl-5-isoxazolyl)sulphanilamide
  • Sulfadimethylisoxazole
  • Sulfafurazol
  • Sulfafurazole
  • Sulfafurazolum
  • Sulfaisoxazole
  • Sulfasoxazole
  • Sulfisonazole
  • Sulfisoxasole
  • Sulfisoxazol
  • Sulfofurazole
  • Sulphadimethylisoxazole
  • Sulphafurazol
  • Sulphafurazole
  • Sulphaisoxazole
  • Sulphisoxazol
  • Sulphofurazole
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 127-69-5
ATC: J01EB05, S01AB02
ĐG : Amend
CTHH: C11H13N3O3S
PTK: 267.304
A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C11H13N3O3S
Phân tử khối
267.304
Monoisotopic mass
267.067761987
InChI
InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
InChI Key
InChIKey=NHUHCSRWZMLRLA-UHFFFAOYSA-N
IUPAC Name
4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
Traditional IUPAC Name
sulfisoxazole
SMILES
CC1=NOC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1C
Độ tan chảy
191 °C
Độ hòa tan
300 mg/L (at 37 °C)
logP
1.01
logS
-2.91
pKa (strongest acidic)
5.8
pKa (Strongest Basic)
2.17
PSA
98.22 Å2
Refractivity
67.92 m3·mol-1
Polarizability
26.93 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
pKa
5
Dược Lực Học : Sulfisoxazole 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 : A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms. [PubChem] Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Dược Động Học :

▧ Route of Elimination :
The mean urinary excretion recovery following oral administration of sulfisoxazole is 97% within 48 hours, of which 52% is intact drug, with the remaining as the N4-acetylated metabolite. It is excreted in human milk.
Độc Tính : LD50=6800 mg/kg (Orally in mice)
Chỉ Định : For the treatment of severe, repeated, or long-lasting urinary tract infections, meningococcal meningitis, acute otitis media, trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis, malaria and other bacterial infections.
Tương Tác Thuốc :
  • Chlorpropamide Sulfonamide/sulfonylurea: possible hypoglycemia
  • Methotrexate The sulfamide increases the toxicity of methotrexate
  • Tamoxifen Sulfisoxazole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfisoxazole is initiated, discontinued or dose changed.
  • Tolbutamide Tolbutamide and Sulfisoxazole 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 Sulfisoxazole, 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 Sulfisoxazole is initiated, discontinued or dose changed.
  • Trimethoprim The strong CYP2C9 inhibitor, Sulfisoxazole, 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 Sulfisoxazole is initiated, discontinued or dose changed.
  • Voriconazole Sulfisoxazole, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if sulfisoxazole is initiated, discontinued or dose changed.
  • Warfarin Sulfisoxazole, 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 sulfisoxazole is initiated, discontinued or dose changed.
  • Zafirlukast Sulfisoxazole, 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 sulfisoxazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Roche
    Sản phẩm biệt dược : Gantrisin
  • Công ty :
    Sản phẩm biệt dược : Neoxazol
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00263
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5344
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505342
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07318
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00450
ChemSpider
http://www.chemspider.com/Chemical-Structure.5151.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50034452
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0004-1003-28
PharmGKB
http://www.pharmgkb.org/drug/PA164748964
Wikipedia
http://en.wikipedia.org/wiki/Sulfisoxazole
Drugs.com
http://www.drugs.com/mtm/sulfisoxazole-ophthalmic.html
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