Sulfaguanidine

Sulfaguanidin.svg

Sulfaguanidine is a sulfonamide antibiotic that was historically used to treat bacterial infections. It is a derivative of sulfanilamide and is known for its relatively low solubility in water, which makes it suitable for treating infections in the gastrointestinal tract.

Chemical Properties

Sulfaguanidine, also known as sulfanilylguanidine, has the chemical formula C7H10N4O2S. It is a white, crystalline powder that is practically insoluble in water but soluble in dilute acids and alkalies. The compound is synthesized by the reaction of sulfanilamide with cyanamide.

Mechanism of Action

Sulfaguanidine works by inhibiting the synthesis of folic acid in bacteria. It competes with para-aminobenzoic acid (PABA) for the enzyme dihydropteroate synthase, which is crucial for the production of folic acid. Without folic acid, bacteria cannot synthesize DNA, RNA, and essential proteins, leading to their death.

Uses

Sulfaguanidine was primarily used to treat bacterial dysentery and other infections of the gastrointestinal tract. Its low solubility in water means it remains in the gut, making it effective for treating infections localized in the intestines.

Side Effects

Common side effects of sulfaguanidine include nausea, vomiting, and diarrhea. In some cases, it can cause allergic reactions such as rash, itching, and fever. Prolonged use can lead to more severe side effects like blood dyscrasias and kidney damage.

History

Sulfaguanidine was one of the early sulfonamide antibiotics developed in the 1930s. It was widely used during World War II to treat intestinal infections among soldiers. However, with the advent of more effective and less toxic antibiotics, its use has significantly declined.

Current Status

Today, sulfaguanidine is rarely used in clinical practice due to the availability of more effective antibiotics with fewer side effects. It is primarily of historical interest and is occasionally used in veterinary medicine.

See Also

• Sulfonamide
• Antibiotic
• Bacterial infection
• Folic acid synthesis
• Sulfanilamide

External Links

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