Sulfamethoxazole

Synonym(s): Sulfisomezole  |  sulfamethalazole  |  sulfamethazole

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; intermediate-acting (8-12 hours). Mostly used in fixed combination with trimethoprim (synergistic combination) for treatment and prophylaxis (oral and iv).
Year first mentioned:	1950
Development status:	Approved, off-patent, discontinued in most countries as monotherapy

Chemical structure(s):
Canonical SMILES:	CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES:	CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI:	InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChI Key:	JLKIGFTWXXRPMT-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5329

External links:
Guide to Pharmacology:	sulfamethoxazole
Citation:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8046889/