Pivampicillin
Encyclopedia
Pivampicillin is a pivaloyloxymethylester of ampicillin
. It is a prodrug
, which is thought to enhance the oral bioavailability
of ampicillin because of its greater lipophilicity compared to that of ampicillin.
when broken down by the body—such as pivampicillin, pivmecillinam
and cefditoren pivoxil—have long been known to deplete levels of carnitine
. This is not due to the drug itself, but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine, it is unlikely to be of clinical significance; long-term use, however, appears problematic and is not recommended.
Ampicillin
Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. Until the introduction of ampicillin by the British company Beecham, penicillin therapies had only been effective against Gram-positive organisms such as staphylococci and streptococci...
. It is a prodrug
Prodrug
A prodrug is a pharmacological substance administered in an inactive form. Once administered, the prodrug is metabolised in vivo into an active metabolite, a process termed bioactivation. The rationale behind the use of a prodrug is generally for absorption, distribution, metabolism, and...
, which is thought to enhance the oral bioavailability
Bioavailability
In pharmacology, bioavailability is a subcategory of absorption and is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. By definition, when a medication is administered...
of ampicillin because of its greater lipophilicity compared to that of ampicillin.
Adverse effects
Prodrugs that release pivalic acidPivalic acid
Pivalic acid is a carboxylic acid with a molecular formula of 3CCO2H. This colourless, odiferous organic compound is solid at room temperature.-Industrial route:...
when broken down by the body—such as pivampicillin, pivmecillinam
Pivmecillinam
Pivmecillinam or amdinocillin pivoxil is an orally-active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam...
and cefditoren pivoxil—have long been known to deplete levels of carnitine
Carnitine
Carnitine is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. In living cells, it is required for the transport of fatty acids from the cytosol into the mitochondria during the breakdown of lipids for the generation of metabolic energy. It is widely...
. This is not due to the drug itself, but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine, it is unlikely to be of clinical significance; long-term use, however, appears problematic and is not recommended.