Pivmecillinam

Pivmecillinam
ATC Code J01CA08
Formula C21H33N3O5S
Molar Mass (g·mol−1) 439,569
Physical State solid
Melting Point (°C) 119
PKS Value 8,9
CAS Number 32886-97-8
PUB Number 115163
Drugbank ID DB01605
Solubility soluble in water

Basics

Pivmecillinam is an active substance from the group of ß-lactam antibiotics. It is used in the treatment of uncomplicated urinary tract infections caused by mecillinam-sensitive bacteria. The antibiotic is mainly effective against Gram-negative enterobacteria such as Escherichia coli, Shigella and Salmonella, but not against Gram-positive bacteria.

Pharmacology

Pharmacodynamics

Like other of the ß-lactam antibiotics, pivmecillinam interferes with the biosynthesis of the bacterial cell wall in that the opened ß-lactam ring inhibits the enzyme D-alanine transpeptidase. The terminal alanine residues can now no longer combine with glycine, resulting in instabilization of the cell wall and thus killing the bacterium.

The multiplication of the bacteria is inhibited by the antibiotic binding to penicillin binding protein 2 (PBP 2). Since other penicillins and cephalosporins mainly bind only to PBP 1 and 3, cross-resistance rarely occurs.

Pharmacokinetics

Pivmecillinam is an inactive precursor of mecillinam, which is well absorbed orally and degraded in the intestinal mucosa to amdinocillin. Like other penicillins, the half-life is only about one hour. The antibiotic is excreted primarily by the kidney.

Interactions

Excretion of the antibiotic decreases with concomitant use with probenecid.
Pivmecillinam selbst reduziert die Ausscheidung des Zytostatikums Methotrexat.
Das Risiko eines Carnitinmangels erhöht sich bei gleichzeitiger Einnahme von Pivmecillinam mit Valproinsäure.

Toxicity

Side effects

The most common unwanted side effects of pivmecillinam include gastrointestinal symptoms such as nausea and diarrhea, and allergic reactions or skin rashes. Fungal infections of the vagina are also common.

Toxicological data

LD50 (mouse, oral): 3020 mg/kg
LD50 (Maus, intravenös): 475 mg/kg
LD50 (Maus, subkutan): 1736 mg/kg

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The contents shown do not replace the original package insert of the medicinal product, especially with regard to dosage and effect of the individual products. We cannot assume any liability for the correctness of the data, as the data was partly converted automatically. A doctor should always be consulted for diagnoses and other health questions. Further information on this topic can be found here.