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Questions and Answers
What year was Prontosil first discovered as an effective treatment for streptococcal infections in mice?
What year was Prontosil first discovered as an effective treatment for streptococcal infections in mice?
What is the primary reason sulfonamides have largely been replaced by antibiotics?
What is the primary reason sulfonamides have largely been replaced by antibiotics?
What active ingredient is released from the metabolic breakdown of Prontosil?
What active ingredient is released from the metabolic breakdown of Prontosil?
Who was awarded the Nobel Prize for their discovery of Prontosil?
Who was awarded the Nobel Prize for their discovery of Prontosil?
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What characteristics does sulfanilamide possess as an antibacterial agent?
What characteristics does sulfanilamide possess as an antibacterial agent?
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What is the primary reason why sulfonamide resistance can be transferred between bacterial species?
What is the primary reason why sulfonamide resistance can be transferred between bacterial species?
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Which of the following measures can help decrease the side effects associated with sulphanilamide usage?
Which of the following measures can help decrease the side effects associated with sulphanilamide usage?
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What is the historical significance of sulfanilamides in antibacterial treatment?
What is the historical significance of sulfanilamides in antibacterial treatment?
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What is the impact of urine pH on sulfonamide solubility?
What is the impact of urine pH on sulfonamide solubility?
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Which of the following is a potential side effect of sulphanilamide treatment?
Which of the following is a potential side effect of sulphanilamide treatment?
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Flashcards
Prontosil's discovery
Prontosil's discovery
Prontosil, a red dye, was found to effectively treat streptococcal infections in mice in 1932.
Sulfonamides' activity
Sulfonamides' activity
Sulfonamides work against both gram-positive and gram-negative bacteria.
Prontosil's inactive nature in vitro
Prontosil's inactive nature in vitro
Prontosil, though effective in treating infections in living organisms (in vivo), showed no antibacterial effect in lab tests.
Sulfonamides' prodrug role
Sulfonamides' prodrug role
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Sulfanilamide
Sulfanilamide
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Sulfonamide Resistance Mechanism
Sulfonamide Resistance Mechanism
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Sulfonamide Solubility and pH
Sulfonamide Solubility and pH
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Sulfonamide Side Effect
Sulfonamide Side Effect
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Sulfonamide Application
Sulfonamide Application
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Improving Sulfonamide Solubility
Improving Sulfonamide Solubility
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Study Notes
Discovery of Sulfonamides
- Sulfonamides are synthetic compounds active against gram-positive and gram-negative bacteria.
- Initially synthesized as azo dyes in Germany, aiming to create antimicrobial dyes.
- Gerhard Domagk (1895-1964) discovered the antibacterial effects of Prontosil, a precursor to sulfanilamide, winning a Nobel Prize in 1939.
Folic Acid Inhibitors
- Prontosil, initially, is inactive in vitro, but highly active in vivo.
- Prontosil breaks down to release the active ingredient, sulfanilamide.
- Sulfanilamide is a first synthetic antibacterial agent.
- Sulfonamides are competitive inhibitors of dihydropteroate synthetase.
- They inhibit the bacterial enzyme that produces folic acid.
- This is crucial because bacteria, unlike humans, must synthesize folic acid for vital metabolic processes.
Mechanism of Action
- Sulfonamides resemble the structure of a substrate called para-aminobenzoic acid (PABA).
- They compete with PABA for an enzyme’s active site.
- Bacteria can't use the sulfonamide, instead it inhibits the bacterial enzyme which prevents bacteria from using folic acid.
- Resistance can emerge by bacteria producing more PABA.
Structure-Activity Relationships (SAR)
- Aromatic rings are crucial for activity.
- Changes in the structure of the aromatic rings and aromatic groups can affect the potency of the compound.
- The para position on the aminobenzoic acid is critical.
- Substituents in the para-position affect the compounds activity.
- The group at the 4 position of the structure is critical for solubility and potency.
- Sulfonamide nitrogen must be primary or secondary for activity.
Prodrugs
- Some sulfonamides are prodrugs, meaning they are inactive in their original form but are converted into active metabolites inside the body.
- N-acetylation is a common metabolic step that increases the hydrophobic nature of some sulfonamide analogs.
Side Effects
- Sulfonamides can cause kidney damage as they form crystals in the urine.
- To reduce side effects, patients should drink a lot of water, and the pH of the urine can be adjusted.
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