Phthalylsulfathiazole

Phthalylsulfathiazole

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A07AB02 (WHO)
Identifiers
IUPAC name 2-[({4-[(1,3-Thiazol-2-ylamino)sulfonyl]phenyl}amino)carbonyl]benzoic acid
CAS Number	85-73-4 N
PubChem CID	4806
DrugBank	DB13248 Y
ChemSpider	4641 N
UNII	6875L5852V
KEGG	D02440 Y
ChEMBL	ChEMBL1524273 N
CompTox Dashboard (EPA)	DTXSID8023470
ECHA InfoCard	100.001.480
Chemical and physical data
Formula	C17H13N3O5S2
Molar mass	403.43 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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)

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.

The drug is indicated in the treatment of dysentery, colitis, gastroenteritis and intestinal surgery. It is a derivative of sulfathiazole in which the phthalic acid substitution on the aniline nitrogen prevents it from being absorbed into the blood stream from the gut. Adverse effects may include allergic reactions, vitamin B insufficiency, agranulocytosis, and aplastic anemia.