Pivampicillin is a

pivaloyloxymethyl Pivaloyloxymethyl (POM, pivoxil, pivoxyl) is a protecting group used in organic synthesis.''Protective Groups in Organic Synthesis'', 3rd Edition, Theodora M. Greene and Peter G. M. Wuts, The POM radical has the formula (CH3)3C-CO-O-CH2. The PO ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

ampicillin Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis. It may also be used to prevent group B strepto ...

. It is a

prodrug A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...

, which is thought to enhance the oral

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

of ampicillin because of its greater

lipophilicity Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...

compared to that of ampicillin.

Adverse effects

Prodrugs that release

pivalic acid Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. A common abbreviation for the pivalyl or pivaloyl group (''t''-BuC(O)) is Piv and for pivalic acid ...

when broken down by the body—such as pivampicillin,

pivmecillinam Pivmecillinam ( INN) or amdinocillin pivoxil (USAN, trade names Selexid, Penomax and Coactabs) is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam. Piv ...

, and

cefditoren pivoxil Cefditoren, also known as cefditoren pivoxil is an antibiotic used to treat infections caused by Gram-positive and Gram-negative bacteria that are resistant to other antibiotics. It is mainly used for treatment of community acquired pneumonia. ...

—have long been known to deplete levels of

carnitine Carnitine is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria. In support of energy metabolism, carnitine transports long-chain fatty acids into mitochondria to be oxidized for energy production, an ...

. This effect 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, is not recommended.

Availability

Worldwide, pivampicillin is only available in Denmark, where it is sold as Pondocillin® by PharmaCoDane, or Miraxid® by

LEO Pharma LEO Pharma A/S is a multinational Danish pharmaceutical company, founded in 1908, with a presence in about 100 countries. Its headquarters are in Ballerup, near Copenhagen The company is 100% integrated into a private foundation owned by the LEO F ...

References

Penicillins Prodrugs Formals {{antibiotic-stub