|Trade names||Veetids, Apocillin, others|
|Other names||penicillin phenoxymethyl, penicillin V, penicillin VK|
|Elimination half-life||30–60 min|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||350.39 g·mol−1|
|3D model (JSmol)|
|Melting point||120–128 °C (248–262 °F)|
Phenoxymethylpenicillin, also known as penicillin V and penicillin VK, is an antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for the treatment of strep throat, otitis media, and cellulitis. It is also used to prevent rheumatic fever and to prevent infections following removal of the spleen. It is given by mouth.
Side effects include diarrhea, nausea, and allergic reactions including anaphylaxis. It is not recommended in those with a history of penicillin allergy. It is relatively safe for use during pregnancy. It is in the penicillin and beta lactam family of medications. It usually results in bacterial death.
Phenoxymethylpenicillin was first made in 1948. It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is about US$0.05–0.96 per day. In the United States a course of treatment costs less than $25. In 2016 it was the 235th most prescribed medication in the United States with more than 2 million prescriptions.
- Infections caused by Streptococcus pyogenes
- Anthrax (mild uncomplicated infections)
- Lyme disease (early stage in pregnant women or young children)
- Rheumatic fever (primary and secondary prophylaxis)
- Streptococcal skin infections
- Spleen disorders (pneumococcal infection prophylaxis)
- Initial treatment for dental abscesses
- Moderate-to-severe gingivitis (with metronidazole)
- Avulsion injuries of teeth (as an alternative to tetracycline)
- Blood infection prophylaxis in children with sickle cell disease.
Penicillin V is sometimes used in the treatment of odontogenic infections.
It is less active than benzylpenicillin (penicillin G) against Gram-negative bacteria. Phenoxymethylpenicillin has a range of antimicrobial activity against Gram-positive bacteria that is similar to that of benzylpenicillin and a similar mode of action, but it is substantially less active than benzylpenicillin against Gram-negative bacteria.
Phenoxymethylpenicillin is more acid-stable than benzylpenicillin, which allows it to be given orally.
Phenoxymethylpenicillin is usually used only for the treatment of mild to moderate infections, and not for severe or deep-seated infections since absorption can be unpredictable. Except for the treatment or prevention of infection with Streptococcus pyogenes (which is uniformly sensitive to penicillin), therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response. People treated initially with parenteral benzylpenicillin may continue treatment with phenoxymethylpenicillin by mouth once a satisfactory response has been obtained.
Phenoxymethylpenicillin is usually well tolerated but may occasionally cause transient nausea, vomiting, epigastric distress, diarrhea, constipation, acidic smell to urine and black hairy tongue. A previous hypersensitivity reaction to any penicillin is a contraindication.
Mechanism of action
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