Pivmecillinam or amdinocillin pivoxil (USAN, trade names Selexid, Penomax and Coactabs) is an orally-active 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...

 of mecillinam

Mecillinam

Mecillinam or amdinocillin , trade name Coactin, is an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 , and is only considered to be active against Gram-negative bacteria. It is used primarily in the treatment of urinary tract infections, and has...

, an extended-spectrum penicillin

Penicillin

Penicillin is a group of antibiotics derived from Penicillium fungi. They include penicillin G, procaine penicillin, benzathine penicillin, and penicillin V....

 antibiotic

Antibiotic

An antibacterial is a compound or substance that kills or slows down the growth of bacteria.The term is often used synonymously with the term antibiotic; today, however, with increased knowledge of the causative agents of various infectious diseases, antibiotic has come to denote a broader range of...

. Pivmecillinam is the pivaloyloxymethyl

Pivalic 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:...

 ester

Carboxylate ester

A carboxylate ester is a carboxylic acid ester.Typically, the term "ester" refers to a carboxylate ester, but technically, the parent acid of an ester can be any acid.For example, methyl formate is a carboxylate ester....

 of mecillinam. Neither drug is available in the United States.

Pivmecillinam is only considered to be active against Gram-negative bacteria, and is used primarily in the treatment of lower urinary tract infection

Urinary tract infection

A urinary tract infection is a bacterial infection that affects any part of the urinary tract. Symptoms include frequent feeling and/or need to urinate, pain during urination, and cloudy urine. The main causal agent is Escherichia coli...

s. In the Nordic countries

Nordic countries

The Nordic countries make up a region in Northern Europe and the North Atlantic which consists of Denmark, Finland, Iceland, Norway and Sweden and their associated territories, the Faroe Islands, Greenland and Åland...

, pivmecillinam has been widely used in that indication since the 1970s. It has been proposed as the first-line drug of choice for empirical treatment

Empirical treatment

Empirical treatment is a medical treatment not derived from the scientific method, but derived from observation, survey or common use.In the medical profession, the term is also used when treatment is started before a diagnosis is confirmed The most common reason is that investigations are...

 of acute cystitis

Cystitis

Cystitis is a term that refers to urinary bladder inflammation that results from any one of a number of distinct syndromes. It is most commonly caused by a bacterial infection in which case it is referred to as a urinary tract infection.-Signs and symptoms:...

. It has also been used to treat paratyphoid fever

Paratyphoid fever

Paratyphoid fevers or Enteric fevers are a group of enteric illnesses caused by serotypic strains of the Salmonella genus of bacteria, S. Paratyphi....

.

Adverse effects

The adverse effect

Adverse drug reaction

An adverse drug reaction is an expression that describes harm associated with the use of given medications at a normal dosage. ADRs may occur following a single dose or prolonged administration of a drug or result from the combination of two or more drugs...

 profile of pivmecillinam is similar to that of other penicillins. The most common side effects of mecillinam use are rash

Rash

A rash is a change of the skin which affects its color, appearance or texture. A rash may be localized in one part of the body, or affect all the skin. Rashes may cause the skin to change color, itch, become warm, bumpy, chapped, dry, cracked or blistered, swell and may be painful. The causes, and...

 and gastrointestinal upset, including nausea

Nausea

Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...

 and vomiting

Vomiting

Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...

.

Prodrugs that release pivalic acid

Pivalic 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 pivmecillinam, pivampicillin

Pivampicillin

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.-Adverse effects:...

 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.