Phthalylsulfathiazole

Phthalylsulfathiazole

Systematic (IUPAC) name
2-[({4-[(1,3-thiazol-2-ylamino)sulfonyl]phenyl}amino)carbonyl]benzoic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	85-73-4
ATC code	A07AB02 (WHO)
PubChem	CID: 4806
ChemSpider	4641 N
UNII	6875L5852V Y
KEGG	D02440 Y
ChEMBL	CHEMBL1524273 N
Chemical data
Formula	C17H13N3O5S2
Molecular mass	403.43222 g/mol
SMILES 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 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 if based on competitive antagonism with para-aminobenzoic acid and inhibition of dihydropteroate synthetase activity, that in turn leads to impaired synthesis of dihydrofolic acid and as a result its active metabolite that is necessary for the synthesis of purine and pyrimidine.

The drug is indicated in treatment of dysentery, colitis, gastroenteritis and intestinal surgery. It doesn't get absorbed into blood stream from the gut. Adverse effects may include allergic reactions, vitamin B insufficiency, agranulocytosis and aplastic anemia.

Synthesis

Phthalylsulfathiazole synthesis: U.S. Patent 2,324,013 U.S. Patent 2,324,015