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