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Bacampicillin | CAS No: 50972-17-3 | GMP-certified suppliers

A medication that treats bacterial infections of the respiratory tract, skin, urinary tract, and gonorrhea caused by susceptible Gram-positive and Gram-negative organisms.

Therapeutic categories

AmidesAnti-Bacterial AgentsAnti-Infective AgentsAntibacterials for Systemic UseAntiinfectives for Systemic UseBeta-Lactam Antibacterials
Generic name
Bacampicillin
Molecule type
small molecule
CAS number
50972-17-3
DrugBank ID
DB01602
Approval status
Approved drug, Investigational drug
ATC code
J01CR50

Primary indications

  • For infections at the following sites: upper and lower respiratory tract
  • Skin and soft tissue
  • Urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: streptococci (including <i>S
  • Faecalis</i> and <i>S

Product Snapshot

  • Bacampicillin is formulated as an oral tablet of a small molecule antibiotic
  • It is primarily used for the treatment of bacterial infections in the respiratory tract, skin and soft tissue, urinary tract, and acute uncomplicated gonococcal urethritis caused by specific Gram-positive and Gram-negative organisms
  • The product is approved for use in the Canadian market and is also in investigational stages

Clinical Overview

Bacampicillin is an oral prodrug of ampicillin belonging to the penicillin class of beta-lactam antibacterials. It is microbiologically inactive in its administered form and undergoes enzymatic hydrolysis by esterases in the intestinal wall during absorption. This transformation releases active ampicillin, which exerts bactericidal effects by inhibiting the biosynthesis of bacterial cell wall mucopeptides. This disruption ultimately compromises cell wall integrity, leading to bacterial cell death.

Bacampicillin is indicated for the treatment of infections caused by susceptible bacteria at diverse sites including the upper and lower respiratory tract, skin and soft tissue, urinary tract infections, and acute uncomplicated gonococcal urethritis. The antimicrobial spectrum encompasses Gram-positive organisms such as streptococci (including S. faecalis and S. pneumoniae) and non-penicillinase-producing staphylococci, as well as Gram-negative species including Haemophilus influenzae, Neisseria gonorrhoeae, Escherichia coli, Proteus mirabilis, Salmonella spp., and Shigella spp.

After oral administration, bacampicillin is efficiently absorbed and rapidly converted to ampicillin, enabling systemic antibacterial activity. Ampicillin is primarily excreted renally, and dosage adjustment may be necessary in renal impairment. Detailed pharmacokinetic parameters such as half-life or bioavailability specific to bacampicillin are consistent with its conversion to ampicillin but vary based on patient populations.

Safety considerations align with those typical of extended-spectrum penicillins, including hypersensitivity reactions, gastrointestinal disturbances, and a risk of superinfections with prolonged use. Bacampicillin is recognized as an approved agent for systemic antibacterial therapy in multiple regulatory jurisdictions.

For active pharmaceutical ingredient procurement, the synthetic route must ensure the preservation of the ester prodrug moiety to maintain effective hydrolysis in vivo. Quality control should confirm chemical identity, purity, and absence of degradation products, with attention to ester stability under storage and transport conditions. Given its prodrug status, consistent conversion to ampicillin on administration is critical for clinical efficacy.

Identification & chemistry

Generic name Bacampicillin
Molecule type Small molecule
CAS 50972-17-3
UNII 8GM2J22278
DrugBank ID DB01602

Pharmacology

SummaryBacampicillin is a prodrug that is enzymatically converted to ampicillin during gastrointestinal absorption. Ampicillin exerts bactericidal effects by inhibiting penicillin-binding proteins involved in bacterial cell wall synthesis. This mechanism targets a range of Gram-positive and Gram-negative bacteria associated with respiratory, urinary, and soft tissue infections.
Mechanism of actionDuring absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides.
PharmacodynamicsBacampicillin is a prodrug of ampicillin and is microbiologically inactive.
Targets
TargetOrganismActions
Penicillin-binding proteinGram positive and gram negative bacteriainhibitor

ADME / PK

AbsorptionAbsorbed following oral administration.

Formulation & handling

  • Bacampicillin is a small molecule penicillin-class antibiotic formulated for oral administration, primarily as tablets.
  • Formulations should consider the reduced bioavailability at elevated gastric pH; separation from antacids is recommended.
  • Food intake may affect absorption variability; dosing can occur with or without food, but food may reduce bioavailability.

Regulatory status

LifecycleThe active pharmaceutical ingredient (API) has passed its primary patent expiration and is currently marketed in Canada, where its market entry is characterized by established availability and generic competition.
MarketsCanada
Supply Chain
Supply chain summaryBacampicillin is primarily manufactured and supplied by a limited number of originator companies with branded products available in the Canadian market. The presence of branded tablets at multiple dosages suggests established market segmentation. Patent expiry status indicates potential for existing or upcoming generic competition, though the global branded product footprint appears concentrated outside major US and EU markets.

Bacampicillin 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.


Bacampicillin (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.