Sulfisoxazole

Class: Antibacterial sulfonamide (sulfa drug)

Spectrum of activity:	Gram-positive  &  Gram-negative
Details of activity:	Sulphonamides are structural analogues of p-aminobenzoic acid and act as competitive inhibitors (and alternate substrates) of dihydropteroate synthase (DHPS) to block the synthesis of folic acid. Primarily bacteriostatic; rapid emergence of resistance.
Description:	Synthetic sufanilamide derivative; short-acting (4-8 hours). Oral and topical application.
Year first mentioned:	1949
Development status:	Approved, off-patent, discontinued in most countries

Chemical structure(s):
Canonical SMILES:	CC1=C(NS(=O)(=O)C2=CC=C(C=C2)N)ON=C1C
Isomeric SMILES:	CC1=C(ON=C1C)NS(=O)(=O)C2=CC=C(C=C2)N
InChI:	InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
InChI Key:	NHUHCSRWZMLRLA-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5344

External links:
Guide to Pharmacology:	sulfisoxazole
Main Source:	https://pubmed.ncbi.nlm.nih.gov/14795570/
Citations:	https://pubmed.ncbi.nlm.nih.gov/35820309/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8046889/