Phthalylsulfathiazole

Phthalylsulfathiazole (also known as sulfathalidine) belongs to the group of drugs called sulfonamides. The drug is a broad-spectrum antimicrobial that can treat different types of infections including intestinal. The mechanism of action depends on competitive antagonism with para-aminobenzoic acid and inhibition of dihydropteroate synthetase activity, which in turn leads to impaired synthesis of dihydrofolic acid and as a result its active metabolite necessary for the synthesis of purine and pyrimidine.

Phthalylsulfathiazole
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 2-[({4-[(1,3-Thiazol-2-ylamino)sulfonyl]phenyl}amino)carbonyl]benzoic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.480
Chemical and physical data
FormulaC17H13N3O5S2
Molar mass403.43 g·mol−1
3D model (JSmol)
  • OC(=O)c1ccccc1C(=O)Nc2ccc(cc2)S(=O)(=O)Nc3nccs3 C1=CC=C(C(=C1)C(=O)NC2=CC=C(C=C2)S(=O)(=O)/N=C\3/NC=CS3)C(=O)O
  • InChI=1S/C17H13N3O5S2/c21-15(13-3-1-2-4-14(13)16(22)23)19-11-5-7-12(8-6-11)27(24,25)20-17-18-9-10-26-17/h1-10H,(H,18,20)(H,19,21)(H,22,23) N
  • Key:PBMSWVPMRUJMPE-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

The drug is indicated in the treatment of dysentery, colitis, gastroenteritis and intestinal surgery. It is not absorbed into the blood stream from the gut due to extra n⁴ substitute. Adverse effects may include allergic reactions, vitamin B insufficiency, agranulocytosis and aplastic anemia.


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