Phthalylsulfathiazole
Chemical compound
From Wikipedia, the free encyclopedia
Phthalylsulfathiazole (also known as sulfathalidine)[1] is a sulfonamide broad-spectrum antimicrobial used primarily for treating gastrointestinal infections.[2][3]
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| ECHA InfoCard | 100.001.480 |
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| Formula | C17H13N3O5S2 |
| Molar mass | 403.43 g·mol−1 |
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Medical uses
Phthalylsulfathiazole is indicated for treating various intestinal conditions, including dysentery, colitis, gastroenteritis, and for preoperative preparation in intestinal surgery.[2][4] It may be administered in combination with other antimicrobials such as metronidazole, furazolidone, or neomycin for enhanced efficacy.[3]
Like all antibiotics, phthalylsulfathiazole should be carefully monitored to avoid promoting bacterial resistance.[3]
Available forms
Phthalylsulfathiazole is typically given orally in tablet form to target intestinal infections directly.[2] Due to the phthalic acid substitution on the aniline nitrogen, it remains unabsorbed in the bloodstream, focusing its action within the gut.[5]
Adverse Effects
Common side effects include nausea, stomach upset, and skin rash.[6] Rare but serious adverse effects may involve vitamin B deficiency, agranulocytosis, or aplastic anemia.[7]
Mechanism of action
Phthalylsulfathiazole acts by competitive antagonism with para-aminobenzoic acid, inhibiting the dihydropteroate synthetase enzyme crucial for dihydrofolic acid synthesis. This inhibition disrupts purine and pyrimidine synthesis, impairing bacterial growth and reproduction.[8] Once in the large intestine, phthalylsulfathiazole hydrolyzes to release sulfathiazole, the active antimicrobial component.[9]
