What is sulfonamide?

From the Guidelines

Sulfonamide is a class of antimicrobials that are structurally different from nonantimicrobial sulfonamides due to the presence of an aromatic amine group at the N4 position.

Key Characteristics of Sulfonamides

• Sulfonamide antimicrobials have a distinct structure that sets them apart from nonantimicrobial sulfonamides, which reduces the concern for cross-reactivity between the two groups 1.
• Nonantimicrobial sulfonamides include a variety of drugs such as:
  • Alpha-blockers (e.g., Tamsulosin)
  • Antiarrhythmics (e.g., Ibutilide, sotalol)
  • Anticonvulsants (e.g., Topiramate)
  • Carbonic anhydrase inhibitors (e.g., Acetazolamide, methazolamide, dorzolamide, brinzolamide)
  • COX-2 inhibitors (e.g., Celecoxib)
  • Diuretics (e.g., Furosemide, bumetanide, Hydrochlorothiazide, chlorthalidone, indapamide, metolazone, diazoxide)
  • Sulfonylureas (e.g., Glimepiride, glyburide, gliclazide)
  • Triptans (e.g., Sumatriptan, naratriptan)

Relevance to Clinical Practice

The distinction between sulfonamide antimicrobials and nonantimicrobial sulfonamides is crucial in clinical practice, as it guides the management of patients with a history of sulfonamide allergy or adverse reactions 1.

From the Research

Definition of Sulfonamide

• A sulfonamide is any compound with an SO2NH2 moiety 2
• It is a common structural motif in naturally occurring and synthetic medicinal compounds 3

Types of Sulfonamides

• Sulfonamide antimicrobials, which contain an aromatic amine group at the N4 position 2
• Nonaromatic amines, which include medications such as furosemide, thiazide diuretics, and celecoxib 2

Properties and Applications

• Sulfonamides have been used as antimicrobial agents, anticancer agents, antiglaucoma agents, inhibitors of gamma-secretase, cyclooxgenase-2, and lipoxygenase, anticonvulsivant agents, and hypoglycemic agents 4
• The sulfamide moiety plays important roles in the binding of inhibitors to the active site cavity of enzymes, such as carbonic anhydrases, proteases, and metalloproteases 5
• Sulfonamides have been used to design therapeutic agents with specific biological activities, such as enzyme inhibitors and receptor targeting compounds 5, 3

Biological Activity

• Sulfonamides can cause severe adverse drug reactions, including skin reactions, acute liver injury, pulmonary reactions, and blood dyscrasias 6
• The hydroxylamine and nitroso metabolites of sulfonamides can bind covalently to proteins, resulting in the induction of specific adverse immune responses 6