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Pivampicillin | CAS No: 33817-20-8 | GMP-certified suppliers
A medication that treats respiratory, ear, gynecological, and urinary tract infections caused by susceptible gram-positive and gram-negative bacteria with enhanced oral bioavailability.
Therapeutic categories
Primary indications
- Or the treatment of respiratory tract infections (including acute bronchitis, acute exacerbations of chronic bronchitis and pneumonia)
- Ear, nose and throat infections
- Gynecological infections
- Urinary tract infections (including acute uncomplicated gonococcal urethritis) when caused by non penicillinase-producing susceptible strains of the following organisms: gram-positive organisms, e
Product Snapshot
- Pivampicillin is available as oral capsules, powders for solution, and tablets
- It is primarily used for treating respiratory, ear, nose and throat, gynecological, and urinary tract infections caused by susceptible gram-positive and gram-negative bacteria
- Pivampicillin is approved for use in the Canadian market
Clinical Overview
Clinically, pivampicillin is indicated for the treatment of a range of bacterial infections caused by non-penicillinase-producing susceptible strains. These include respiratory tract infections such as acute bronchitis, acute exacerbations of chronic bronchitis, and pneumonia; ear, nose, and throat infections; gynecological infections; and urinary tract infections, including acute uncomplicated gonococcal urethritis. The spectrum of activity encompasses gram-positive organisms such as streptococci, pneumococci, and staphylococci, as well as gram-negative bacteria including Haemophilus influenzae, Neisseria gonorrhoeae, Escherichia coli, and Proteus mirabilis.
Pharmacodynamically, pivampicillin is inactive until hydrolyzed by nonspecific esterases widely distributed in body tissues. This enzymatic action rapidly converts pivampicillin to the active agent ampicillin, releasing formaldehyde and pivalic acid as byproducts. Conversion occurs in excess of 99% within approximately 15 minutes of absorption. Ampicillin exerts bactericidal activity by inhibiting bacterial cell wall mucopeptide synthesis, leading to cell lysis.
Key pharmacokinetic properties are largely determined by the active metabolite ampicillin. The prodrug formulation enhances oral absorption, yet pivalic acid released during metabolism has been associated with safety considerations, particularly regarding carnitine depletion with prolonged or high-dose use, necessitating caution in susceptible populations.
Pivampicillin belongs to the beta-lactam class of antibiotics, a widely recognized category of antibacterial agents with a broad therapeutic application. It has regulatory approval for systemic use in various jurisdictions and is included among penicillins with extended spectrum activity.
When sourcing pivampicillin API, careful attention should be given to quality attributes, including purity, residual solvent levels, and control of related impurities such as pivalic acid derivatives. Compliance with pharmacopeial standards and regulatory guidelines ensures consistent performance and safety in formulation development.
Identification & chemistry
| Generic name | Pivampicillin |
|---|---|
| Molecule type | Small molecule |
| CAS | 33817-20-8 |
| UNII | 0HLM346LL7 |
| DrugBank ID | DB01604 |
Pharmacology
| Summary | Pivampicillin is a pro-drug rapidly converted to ampicillin, a semi-synthetic penicillin with bactericidal activity. Ampicillin exerts its effect by inhibiting cell wall mucopeptide synthesis through binding to penicillin-binding protein 1A. This mechanism disrupts bacterial cell wall integrity, leading to the treatment of infections caused by susceptible gram-positive and gram-negative organisms. |
|---|---|
| Mechanism of action | Ampicillin (the active metabolite of pivampicillin) has a bactericidal action resulting from inhibition of cell wall mucopeptide biosynthesis. |
| Pharmacodynamics | Pivampicillin is the pivaloyloxymethyl ester of (the semi-synthetic penicillin) ampicillin. It is an inactive pro-drug, which is converted during its absorption from the gastrointestinal tract to the microbiologically active ampicillin, together with formaldehyde and pivalic acid, by non-specific esterases present in most body tissues. Amounts in excess of 99% of the pivampicillin absorbed are converted to ampicillin within 15 minutes of absorption. |
Targets
| Target | Organism | Actions |
|---|---|---|
| Penicillin-binding protein 1A | Clostridium perfringens (strain 13 / Type A) | inhibitor |
ADME / PK
| Absorption | Absorbed following oral administration. |
|---|---|
| Half-life | Approximately 1 hour. |
Formulation & handling
- Pivampicillin is a small molecule antibiotic formulated primarily for oral administration in capsules, tablets, and powder for solution.
- Its moderate logP and low water solubility suggest consideration for solubilization strategies in formulation development.
- The absorption of pivampicillin is not affected by food, allowing flexible dosing with or without meals.
Regulatory status
| Lifecycle | The API has reached post-patent expiry and is established in the Canadian market, with multiple generic versions available and a mature competitive landscape. Ongoing market activity primarily involves generic manufacturing and distribution. |
|---|
| Markets | Canada |
|---|
Supply Chain
| Supply chain summary | Pivampicillin is currently marketed in Canada with branded formulations available as both oral suspension and tablets. The supply landscape involves originator companies producing these branded products primarily in this regional market. Patent expiry status is not indicated, suggesting limited or no generic competition presence to date. |
|---|
Pivampicillin 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.
Pivampicillin (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.
