Pharm
Sulfa Antibiotic
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Sulfa Antibiotic
, Sulfonamide, Sulfanilamide, Sulfisoxazole
See Also
Sulfonamide Allergy
Trimethoprim Sulfamethoxazole
Sulfadiazine
Mechanism
Sulfonamide
Antibiotic
s are natural or synthetic Sulfanilamide derivatives
Sulfonamide
Antibiotic
s are antimetabolites, agents that inhibit DNA, RNA and
Protein
synthesis via
Tetrahydrofolate
path blockade
Sulfonamides are structural analogs of para-aminobenzoic acid (PABA) which is key to microbial
Tetrahydrofolate
synthesis
Sulfonamides competitively inhibit PABA at the dihydropteroate synthase enzyme in production of Dihydropteric acid
Dihydropteric acid is a
Tetrahydrofolate
precursor, and blocking its synthesis, blocks
Bacteria
l DNA, RNA and
Protein
synthesis
Trimethoprim also inhibits
Bacteria
l
Tetrahydrofolate
synthesis (blocks dihydrofolate reductase at tetrahydofolic acid generation)
Sulfonamides precipitate in the urine at therapeutic doses
Limits Sulfonamides alone to subtherapeutic doses
Combining Sulfonamides with other agents (e.g. trimethoprim) allows them to reach therapeutic levels without urine precipitation
Medications
Trimethoprim Sulfamethoxazole
(
Bactrim
,
Septra
)
Covers enteric
Gram Negative Bacteria
(
Urinary Tract Infection
s) and some
Gram Positive
organisms
Also used in
PCP Pneumonia
treatment and prophylaxis (
AIDS
) and MRSA
Skin Infection
s
Sulfadiazine
Broad spectrum activity against both
Gram Positive
and
Gram Negative
organisms
Use limited to
Toxoplasmosis Prevention
and management (combined with
Pyrimethamine
and leucovorin)
Silver Sulfadiazine
Topical Cream
(Silvadene, SSD) has a limited role in
Burn Injury
Sulfisoxazole (Gantrisin)
Primarily indicated in
Urinary Tract Infection
prophylaxis
Higher urine solubility than other Sulfonamides (lower precipitation risk)
Contraindications
Avoid in infant under age 2 months
Sulfonamide Allergy
G6PD Deficiency
Adverse Effects
Gene
ral
Allergic Reaction
or
Anaphylaxis
See
Sulfonamide Allergy
Bone Marrow
suppression (
Agranulocytosis
)
Steven's Johnson Syndrome
Toxic Epidermal Necrolysis
Hepatotoxicity
Hemolysis
(in
G6PD Deficiency
)
Neonatal Hyperbilirubinemia
and
Kernicterus
Sulfonamides compete with
Bilirubin
for albumin binding
Results in increased free
Bilirubin
, with risk of
Neonatal Hyperbilirubinemia
and
Kernicterus
References
Olson (2020) Clinical
Pharmacology
, Medmaster Miami, p. 111
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