Sulfamethoxypyrazine

Synonym(s): Sulfalene  |  Sulfamethopyrazine

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; long-acting (~7 days). Used in combination for protozoal infections.
Year first mentioned:	1953
Development status:	Discontinued in most countries

Chemical structure(s):
Canonical SMILES:	COC1=C(N=CC=N1)NS(=O)(=O)C2=CC=C(C=C2)N
Isomeric SMILES:	COC1=NC=CN=C1NS(=O)(=O)C2=CC=C(C=C2)N
InChI:	InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
InChI Key:	KXRZBTAEDBELFD-UHFFFAOYSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/9047

External links:
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3024282/
Citation:	https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0006732