Hetacillin is a semi-synthetic penicillin antibiotic belonging to the aminopenicillin group. It is a prodrug that is converted in the body to ampicillin, which provides the principal antibacterial activity.
Hetacillin has historically been used for the treatment of susceptible bacterial infections and has been supplied primarily in the form of hetacillin potassium.
Hetacillin is a beta-lactam pharmaceutical API requiring controlled synthesis and purification to maintain appropriate chemical purity, potency and impurity control. Because beta-lactam compounds can be susceptible to degradation, appropriate manufacturing and storage controls are important.
CAS Number: 3511-16-0
Molecular Formula: C19H23N3O4S
Molecular Weight: 389.47 g/mol
Common Salt Form: Hetacillin Potassium
Drug Class: Beta-Lactam Antibiotic
Pharmacological Class: Aminopenicillin
Therapeutic Class: Antibacterial
Therapeutic Area: Infectious Diseases
Hetacillin is converted to ampicillin, which inhibits bacterial cell-wall synthesis. Ampicillin binds to penicillin-binding proteins (PBPs) and interferes with the final stages of peptidoglycan cross-linking.
This weakens the bacterial cell wall and can lead to bacterial cell lysis. Its antibacterial action is therefore bactericidal against susceptible organisms.
Hetacillin has been used for susceptible bacterial infections involving organisms sensitive to ampicillin-type penicillins.
Its historical applications include infections of the:
Current availability and approved clinical use may vary by country.
Hetacillin functions as a prodrug of ampicillin. Following administration, enzymatic conversion produces ampicillin, which is responsible for the principal antibacterial activity.
Hetacillin is a semi-synthetic penicillin containing a beta-lactam ring and thiazolidine-related structure. The free compound has a molecular weight of approximately 389.47 g/mol.
Pharmaceutical material may be supplied as a potassium salt to provide a suitable form for pharmaceutical manufacture.
Hetacillin API quality evaluation may include:
Hetacillin should be stored in a tightly closed container under controlled pharmaceutical conditions and protected from moisture, excessive heat and direct light. Beta-lactam APIs should be handled under validated conditions because hydrolysis can affect product quality.
Hetacillin is relevant to pharmaceutical research involving beta-lactam antibiotics, aminopenicillins, prodrug design and bacterial cell-wall synthesis inhibition.
Hetacillin is a semi-synthetic aminopenicillin and prodrug of ampicillin with CAS Number 3511-16-0, molecular formula C19H23N3O4S, and molecular weight 389.47 g/mol. It produces antibacterial activity following conversion to ampicillin and belongs to the beta-lactam antibiotic class.
| Parameter | Specification |
|---|---|
| Appearance | White to off-white crystalline powder |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | 95.0% – 105.0% |
| Loss on Drying | NMT 1.0% |
| Heavy Metals | NMT 20 ppm |
| pH (1% Solution) | 5.0 – 7.0 |
| Individual Impurity | NMT 1.0% |
| Water Content | NMT 5.0% |