Phenoxymethylpenicillin is a narrow-spectrum antibiotic, also commonly referred to as penicillin V. It is a phenoxymethyl analogue of penicillin G or benzylpenicillin. Phenoxymethylpenicillin is an orally active, naturally occurring penicillin used to treat mild to moderate infections of the respiratory tract, skin, and soft tissues caused by penicillin-susceptible microorganisms. Penicillin V is usually administered as a tablet or solution for parenteral use.
Phenoxymethylpenicillin acts against penicillin-sensitive microorganisms with bactericidal activity. It attacks bacteria during their active multiplication phase by interfering with bacterial cell wall peptidoglycan synthesis. Phenoxymethylpenicillin acts bacteriostatically by binding to specific penicillin-binding proteins (PBPs) located within the bacterial cell wall, which are critical for cell wall synthesis and maintenance, as well as cell division. This disrupts the third and final stage of bacterial cell wall synthesis. This subsequently leads to cell lysis and destruction of the pathogens.
Penicillin V is effective against the following organisms:
When administered orally, phenoxymethylpenicillin is rapidly but incompletely absorbed. The bioavailability of phenoxymethylpenicillin ranges from 25 to 60%. Approximately 50-80% of the given dose is bound to plasma proteins. About 35-70% of an oral dose is metabolized to penicilloic acid, an inactive metabolite. While the drug is rapidly excreted, only 25% of the total dose is detected in the urine. When administered orally, the half-life is approximately 30 minutes. In patients with renal insufficiency, it can last up to 4 hours.
LD50 (rat, oral): >1040 mg/kg
| ATC Code | J01CE02 |
| Formula | C16H18N2O5S |
| Molar Mass (g·mol−1) | 350,39 |
| Physical State | solid |
| Melting Point (°C) | 120–128 |
| PKS Value | 2,73 |
| CAS Number | 87-08-1 |
| PUB Number | 6869 |
| Drugbank ID | DB00417 |
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