Agents
Antibiotics
- Silver Sulfadiazine (Silvadene) (see Silver Sulfadiazine)
- Sulfisomidine (Sulfaisodimidine)
- Sulfacetamide (see Sulfacetamide)
- Sulfadoxine
- Sulfamethoxazole + Trimethoprim (Bactrim, Septra) (see Sulfamethoxazole-Trimethoprim)
- Sulfapyridine: no longer used in humans
Ophthalmologics
- Dichlorphenamide
- Dorzolamide
Diuretics
- Acetazolamide (Diamox) (see Acetazolamide)
- Bumetanide (Bumex) (see Bumetanide)
- Chlorthalidone (Hygroton, Tenoretic) (see Chlorthalidone)
- Clopamide
- Furosemide (Lasix) (see Furosemide)
- Hydrochlorothiazide (HCTZ) (see Hydrochlorothiazide)
- Indapamide (Lozol) (see Indapamide)
- Mefruside
- Metolazone (see Metolazone)
- Xipamide
Anticonvulsants
- Ethoxzolamide
- Sultiame
- Zonisamide
Other
- Celecoxib (Celebrex) (see Celecoxib)
- Darunavir (Prezista) (see Darunavir)
- Mafenide Acetate (Sulfamylon) (see Mafenide Acetate)
- Probenecid (see Probenecid)
- Sulfasalazine (Azulfidine) (see Sulfasalazine)
- Sumatriptan (see Sumatriptan)
- Tamsulosin (Flomax, Omnic) (see Tamsulosin)
Pharmacology
Sulfonamides are Structural Analogs and Competitive Antagonists of Para-Aminobenzoic Acid (PABA) for the Active Site of Dihydropteroate Synthase
- Inhibition of Bacterial PABA Utilization for the Synthesis of Folate
- Folate is Used in Bacterial DNA Synthesis
- Note that Folate is Not Synthesized in Humans and, Therefore, is Required in the Diet: for this reason, sulfonamides are selectively toxic to bacterial cells
- This Mechanism of Action is Similar to that of the Structurally Distinct Sulfone, Dapsone (see Dapsone)
- Sulfonamides are Bacteriostatic
- Sulfamethoxazole (Mechanism as Above) + Trimethoprim (Dihydrofolate Reductase Inhibitor): combination acts synergistically, exhibiting bactericidal action
Adverse Effects
Allergic Adverse Effects
- Sulfonamide Allergy: increased risk in setting of HIV infection (see Human Immunodeficiency Virus)
Dermatologic Adverse Effects
- Drug Rash with Eosinophilia and Systemic Symptoms (DRESS Syndrome) (see Drug Rash with Eosinophilia and Systemic Symptoms)
- Morbilliform Rash (see Exanthems)
Gastrointestinal/Hepatic Adverse Effects
- Asymptomatic Elevation of Hepatic Transaminases (Isolated Transaminitis) (see Drug-Induced Hepatotoxicity)
- Acute Pancreatitis (see Acute Pancreatitis): definite association with acute pancreatitis
Hematologic Advserse Effects
- Increased Risk of Hemolysis in Patient with Glucose-6-Phosphate (G6PD) Deficiency (see Hemolytic Anemia and Glucose-6-Phosphate Dehydrogenase Deficiency)
- Epidemiology
- Definite Risk
- Dapsone (see Dapsone): note that dapsone (diaminodiphenyl sulfone) is a sulfone, structurally dissimilar from the sulfonamides but sharing a similar mechanism of action
- Sulfamethoxazole-Trimethoprim (Bactria, Septra) (see Sulfamethoxazole-Trimethoprim)
- Possible Risk
- Sulfamidine
- Sulfasalazine (Azulfidine) (see Sulfasalazine)
- Doubtful Risk
- Sulfadiazine (see Silver Sulfadiazine)
- Sulfisoxazole
- Definite Risk
- Epidemiology
- Methemoglobinemia (see Methemoglobinemia)
- Reported Agents
- Silver Sulfadiazine
- Reported Agents
Infectious Adverse Effects
- Clostridium Difficile Colitis (see Clostridium Difficile)
- Epidemiology: somewhat common association with sulfonamides (NEJM, 2015) [MEDLINE]
Pulmonary Adverse Effects
- Drug-Induced Pulmonary Esoinophilia (see Drug-Induced Pulmonary Eosinophilia)
- Drug Rash with Eosinophilia and Systemic Symptoms (DRESS Syndrome) (see Drug Rash with Eosinophilia and Systemic Symptoms)
- Hypersensitivity Pneumonitis (see Hypersensitivity Pneumonitis): has been reported with sulfapyridine
Renal Adverse Effects
- Acute Kidney Injury (AKI) (see Acute Kidney Injury): due to intratubular deposition and obstruction
References
- Clostridium difficile infection. N Engl J Med. 2015 Apr 16;372(16):1539-48. doi: 10.1056/NEJMra1403772 [MEDLINE]