sulfisoxazole   Click here for help

GtoPdb Ligand ID: 12700

Synonyms: Gantrisin® | NU-445 | sulfafurazole | sulphafurazole
Approved drug
sulfisoxazole is an approved drug (FDA (1948))
Compound class: Synthetic organic
Comment: Sulfisoxazole (sulfafurazole) is a sulfonamide antibacterial compound [4-5].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 102.16
Molecular weight 267.31
XLogP 0.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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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
No information available.
Summary of Clinical Use Click here for help
Sulfisoxazole is indicated in the treatment of infections caused by susceptible bacteria, including urinary tract infections, meningococcal meningitis and acute otitis media. Sulfisoxazole has been marketed in a number of jurisdictions, including the US, Canada, Australia, Japan and some European countries. However, there is no information regarding current approval for clinical use of this drug on the US FDA or European Medicines Agency (EMA) websites. Individual national approval agencies may have granted marketing authorisation. Marketed formulations may contain sulfisoxazole acetyl or sulfisoxazole diolamine.
Sulfisoxazole is also used in combination with erythromycin or phenazopyridine.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Sulfonamides are structural analogues of 4-aminobenzoic acid (pABA) an intermediate in the de novo synthesis of folate by some prokaryotes, lower eukaryotes and plants [2]. The antibacterial MMOA is competitive inhibition of bacterial dihydropteroate synthase (DHPS) resulting in a block of folate biosynthesis [1].