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QuickView for Sulfisoxazole (compound)


PubChem
Name: Sulfisoxazole
PubChem Compound ID: 10996285
Description: A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms.
Molecular formula: C53H80O2
Molecular weight: 750.194 g/mol
DrugBank
Identification
Name: Sulfisoxazole
Name (isomeric): DB00263
Drug Type: small molecule
Description: A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms.
Synonyms:
Sulfofurazole; Sulphaisoxazole; Sulphafurazol; Sulfisoxazole Dialamine; Sulfaisoxazole; Sulfisoxazole Diolamine; Sulphofurazole; Sulfisoxasole; Sulfasoxazole; Sulfafurazole.
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Brand: Norilgan-S, Saxosozine, Dorsulfan, Soxamide, Roxoxol, Astrazolo, Sulsoxin, Entusul, Tl-Azole, Amidoxal, Unisulf, Sulfasan, Entusil, Stansin, Bactesulf, Sulfagen, Neoxazol, Novazolo, Soxisol, Sulfoxol, Azo Gantrisin, Renosulfan, J-Sul, Sulfagan, Resoxol, Gantrisona, Roxosul Tablets, G-Sox, Sulfapolar, Sodizole, Sulbio, Isoxamin, Soxazole, Dorsulfan Warthausen, Sulfisin, Gantrisin, Suloxsol, Sulfazin, Thiasin, Chemouag, Sulphafuraz, Sulfizol, Barazae, Roxosul, Sulfizole, Novosaxazole, Koro-Sulf, Gantrosan, Azosulfizin, Soxomide, Uritrisin, Soxitabs, Soxo, Neazolin, Sulfizin, Sulfasol, Sosol, SI, V-Sul, Sulfalar, Ganda, Cosoxazole, Sk-Soxazole, Accuzole, Pancid, Alphazole, Vagilia, Gantrisine, Urogan, Urisoxin
Brand name mixture: Renazone Plus Tab(Ammonium Chloride + Atropine Sulfate + Hyoscyamine Hydrobromide + Scopolamine Hydrobromide + Sulfisoxazole), Pediazole(Erythromycin (Erythromycin Ethylsuccinate) + Sulfisoxazole Acetyl)
Category: Anti-Infective Agents, Sulfonamides, Anti-Infectives
CAS number: 127-69-5
Pharmacology
Indication: 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.
Pharmacology:
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-aminob...
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Mechanism of Action:
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 ...
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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.
Toxicity: LD50=6800 mg/kg (Orally in mice)
Affected organisms: Enteric bacteria and other eubacteria
Interactions
Drug interaction:
ZafirlukastSulfisoxazole, 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.
VoriconazoleSulfisoxazole, 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.
WarfarinSulfisoxazole, 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.
ChlorpropamideSulfonamide/sulfonylurea: possible hypoglycemia
TrimethoprimThe 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.
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Enzymes