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- Hetacillin
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Hetacillin | CAS No: 3511-16-8 | GMP-certified suppliers
A medication that serves as a beta-lactam antibiotic prodrug used to treat bacterial infections, primarily targeting gram-positive and certain gram-negative organisms systemically.
Therapeutic categories
Primary indications
- Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections
- In the body it gets converted to ampicillin
Product Snapshot
- Hetacillin is an oral beta-lactam antibiotic prodrug formulated for systemic administration
- It is primarily used for the treatment of bacterial infections
- The compound holds veterinary approval status but has been withdrawn from human medical use
Clinical Overview
Pharmacologically, hetacillin’s bactericidal action derives from its inhibition of bacterial cell wall synthesis. Upon conversion to ampicillin, the molecule targets penicillin-binding proteins (PBPs), which are essential for the cross-linking stage of peptidoglycan formation. This inhibition compromises cell wall integrity, leading to bacterial lysis mediated by autolytic enzymes. Hetacillin itself is designed to be more stable than ampicillin in vitro, resisting premature degradation by intramolecular attack on the beta-lactam ring, although this effect is transient as ampicillin formed is susceptible to beta-lactamase enzymes.
Key ADME characteristics include rapid conversion in the body from hetacillin to ampicillin and acetone. The prodrug approach aimed to improve bioavailability and stability; however, clinical advantages over ampicillin have not been demonstrated. Ampicillin’s known pharmacokinetic profile, including renal excretion and distribution primarily to extracellular fluids, applies to the active moiety.
Safety considerations align with those typical for beta-lactam antibiotics. Hypersensitivity reactions, including anaphylaxis, may occur in penicillin-sensitive individuals. Cross-reactivity with other beta-lactams is a risk factor. No significant unique toxicities distinguish hetacillin beyond those associated with ampicillin.
Hetacillin has been withdrawn from the market in many regions due to the lack of therapeutic superiority compared to non-esterified penicillins like ampicillin. It has limited current clinical usage but remains of historical and pharmaceutical interest.
For sourcing and quality control of hetacillin API, attention should be paid to chemical purity, stereochemical configuration, and stability, given its prodrug nature and susceptibility to hydrolysis. Compliance with pharmacopeial standards for penicillin derivatives and controlled manufacturing environments is essential to ensure reproducible quality and safety profiles.
Identification & chemistry
| Generic name | Hetacillin |
|---|---|
| Molecule type | Small molecule |
| CAS | 3511-16-8 |
| UNII | TN4JSC48CV |
| DrugBank ID | DB00739 |
Pharmacology
| Summary | Hetacillin is a semisynthetic penicillin prodrug that is hydrolyzed in vivo to ampicillin, which exerts bactericidal effects by binding to penicillin-binding proteins (PBPs) and inhibiting bacterial cell wall synthesis. It targets multiple PBPs including PBP1A, PBP1B, PBP2A, PBP2B, and PBP3, leading to disruption of cell wall integrity and bacterial lysis. Hetacillin exhibits activity against a broad spectrum of gram-positive and gram-negative aerobic and anaerobic bacteria. |
|---|---|
| Mechanism of action | Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. _In vitro_ studies have shown that hetacillin is resistant to beta lactamase activity. However, this effect is transient, as the hydrolysis product, ampicillin, is readily inactivated by beta lactamase. Hetacillin locks up the offending amino group and prevents the decomposition of Hetacillin. Once hydrolyzed to ampicillin (and acetone), ampicillin binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. |
| Pharmacodynamics | Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). |
Targets
| Target | Organism | Actions |
|---|---|---|
| Penicillin-binding protein 2a | Streptococcus pneumoniae (strain ATCC BAA-255 / R6) | inhibitor |
| Penicillin-binding protein 1b | Streptococcus pneumoniae (strain ATCC BAA-255 / R6) | inhibitor |
| Penicillin-binding protein 3 | Streptococcus pneumoniae | inhibitor |
ADME / PK
| Metabolism | Hydrolyzed to active ampicillin via esterases |
|---|
Formulation & handling
- Hetacillin is a small molecule penicillin derivative intended primarily for oral administration due to its structural characteristics.
- It exhibits moderate water solubility, which should be considered when designing formulations for optimal bioavailability.
- Stability assessments are critical as penicillin-class compounds may undergo hydrolysis; appropriate storage and handling to minimize moisture exposure are recommended.
Regulatory status
Supply Chain
| Supply chain summary | Hetacillin is manufactured by Bristol Laboratories Inc., a division of Bristol Myers Co, serving as the originator company. The branded product has a global presence, including markets in the US and EU. Given the extended availability of the product, patent expiry has likely enabled existing generic competition within these regions. |
|---|
Hetacillin is a type of Penicillins
Penicillins belong to the subcategory of pharmaceutical active pharmaceutical ingredients (APIs) and play a crucial role in the treatment of various bacterial infections. They are a class of antibiotics derived from the fungus Penicillium, and are widely used in the pharmaceutical industry.
Penicillins exert their antibacterial effect by inhibiting the formation of bacterial cell walls. They target a specific enzyme, called transpeptidase, which is responsible for cross-linking the peptidoglycan chains in the bacterial cell wall. By blocking this process, penicillins weaken the cell wall, leading to its rupture and subsequent bacterial death.
These APIs are classified into several subclasses, such as penicillin G, penicillin V, and extended-spectrum penicillins. Each subclass has unique characteristics and mechanisms of action. Penicillin G, for example, is effective against a broad range of Gram-positive bacteria, while penicillin V is primarily used for oral administration.
The pharmaceutical industry produces penicillins through a fermentation process using Penicillium strains. The obtained penicillin products are then isolated, purified, and formulated into different dosage forms, including tablets, capsules, and injectables.
Penicillins have been instrumental in the treatment of various infections, including respiratory, skin, urinary tract, and sexually transmitted infections. However, it's essential to note that some bacteria have developed resistance to penicillins through different mechanisms, such as the production of beta-lactamases. As a result, pharmaceutical companies have developed combination therapies and modified penicillins to combat antibiotic resistance effectively.
In summary, penicillins are a vital subcategory of pharmaceutical APIs that provide effective treatment options for bacterial infections. Their diverse subclasses, mechanisms of action, and formulations contribute to their widespread use in the medical field.
Hetacillin (Penicillins), classified under Antibacterials
Antibacterials, a category of pharmaceutical active pharmaceutical ingredients (APIs), play a crucial role in combating bacterial infections. These APIs are chemical compounds that target and inhibit the growth or kill bacteria, helping to eliminate harmful bacterial pathogens from the body.
Antibacterials are essential for the treatment of various bacterial infections, including respiratory tract infections, urinary tract infections, skin and soft tissue infections, and more. They are commonly prescribed by healthcare professionals to combat both mild and severe bacterial infections.
Within the category of antibacterials, there are different classes and subclasses of APIs, each with distinct mechanisms of action and target bacteria. Some commonly used antibacterials include penicillins, cephalosporins, tetracyclines, macrolides, and fluoroquinolones. These APIs work by interfering with various aspects of bacterial cellular processes, such as cell wall synthesis, protein synthesis, DNA replication, or enzyme activity.
The development and production of antibacterial APIs require stringent quality control measures to ensure their safety, efficacy, and purity. Pharmaceutical manufacturers must adhere to Good Manufacturing Practices (GMP) and follow rigorous testing protocols to guarantee the quality and consistency of these APIs.
As bacterial resistance to antibiotics continues to be a significant concern, ongoing research and development efforts aim to discover and develop new antibacterial APIs. The evolution of antibacterials plays a crucial role in combating emerging bacterial strains and ensuring effective treatment options for infectious diseases.
In summary, antibacterials are a vital category of pharmaceutical APIs used to treat bacterial infections. They are designed to inhibit or kill bacteria, and their development requires strict adherence to quality control standards. By continually advancing research in this field, scientists and pharmaceutical companies can contribute to the ongoing battle against bacterial infections.
