Hetacillin

Hetacillin

Hetacillin is a beta-lactam antibiotic in the penicillin family. It is a prodrug of ampicillin and is used in the treatment of various bacterial infections. Hetacillin is not commonly used today due to the availability of more effective antibiotics.

History

Hetacillin was first synthesized in the 1960s as part of a series of prodrugs designed to improve the oral bioavailability of ampicillin. The addition of a hydroxyethyl group to the ampicillin molecule resulted in a drug that was more stable in the acidic environment of the stomach, allowing for better absorption and higher blood levels of the active drug.

Pharmacology

As a prodrug, hetacillin is inactive until it is metabolized in the body. The hydroxyethyl group is cleaved off, releasing the active drug, ampicillin. Ampicillin is a broad-spectrum antibiotic that works by inhibiting the synthesis of the bacterial cell wall, leading to cell death.

Clinical Use

Hetacillin was used in the treatment of a variety of bacterial infections, including respiratory tract infections, urinary tract infections, and skin infections. However, the development of more effective and better-tolerated antibiotics has led to its decline in use.

Side Effects

Like other penicillins, hetacillin can cause a range of side effects. These can include allergic reactions, nausea, vomiting, and diarrhea. In rare cases, it can cause more serious side effects such as anaphylaxis or Clostridium difficile-associated diarrhea.

Resistance

Bacterial resistance to hetacillin can occur through several mechanisms. These include the production of beta-lactamase enzymes that can inactivate the drug, and changes in the bacterial cell wall that prevent the drug from binding.

See Also

• Beta-lactam antibiotic
• Penicillin
• Ampicillin
• Prodrug

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