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| Clinical data | |
|---|---|
| Trade names | Veetids, Apocillin,[1] others |
| Other names | penicillin phenoxymethyl, penicillin V, penicillin VK |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a685015 |
| License data | |
| Routes of administration | By mouth |
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| Pharmacokinetic data | |
| Bioavailability | 60% |
| Protein binding | 80% |
| Metabolism | Liver |
| Eliminationhalf-life | 30–60 min |
| Excretion | Kidney |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.001.566 |
| Chemical and physical data | |
| Formula | C16H18N2O5S |
| Molar mass | 350.39 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 78–80 °C (172–176 °F) |
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Phenoxymethylpenicillin, also known aspenicillin V (PcV) andpenicillin VK, is anantibiotic useful for the treatment of a number ofbacterial infections.[2] Specifically it is used for the treatment ofstrep throat,otitis media, andcellulitis.[2] It is also used to preventrheumatic fever and to prevent infections followingremoval of the spleen.[2] It is given by mouth.[2]
Side effects includediarrhea,nausea, andallergic reactions includinganaphylaxis.[2] It is not recommended in those with a history ofpenicillin allergy.[2] It is relatively safe for use duringpregnancy.[3] It is in thepenicillin andbeta lactam family of medications.[4] It usually results inbacterial death.[4]
Phenoxymethylpenicillin was first made in 1948 byEli Lilly.[5]: 121 It is on theWorld Health Organization's List of Essential Medicines.[6] It is available as ageneric medication.[4] In 2023, it was the 248th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[7][8]
Specific uses for phenoxymethylpenicillin include:[9][10]
Penicillin V is sometimes used in the treatment ofodontogenic infections.[citation needed]
It is less active thanbenzylpenicillin (penicillin G) againstGram-negative bacteria.[11][12] Phenoxymethylpenicillin has a range of antimicrobial activity againstGram-positive bacteria that is similar to that of benzylpenicillin and a similar mode of action, but it is substantially less active than benzylpenicillin againstGram-negative bacteria.[11][12]
Phenoxymethylpenicillin is more acid-stable than benzylpenicillin, which allows it to be given orally.[citation needed]
Phenoxymethylpenicillin is usually used only for the treatment of mild to moderate infections, and not for severe or deep-seated infections sinceabsorption can be unpredictable. Except for the treatment or prevention of infection withStreptococcus pyogenes (which is uniformly sensitive to penicillin), therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response.[13] People treated initially withparenteral benzylpenicillin may continue treatment with phenoxymethylpenicillin by mouth once a satisfactory response has been obtained.[9]
It is not active againstbeta-lactamase-producing bacteria, which include many strains ofStaphylococci.[13]
Phenoxymethylpenicillin is usually well tolerated but may occasionally cause transientnausea, vomiting, epigastric distress,diarrhea, constipation, acidic smell to urine andblack hairy tongue. A previoushypersensitivity reaction toanypenicillin is acontraindication.[9][13]
The mechanism of phenoxymethylpenicillin is identical to that of all other penicillins. It exerts abactericidal action against penicillin-sensitive microorganisms during the stage of active multiplication. It acts byinhibiting thebiosynthesis of cell-wallpeptidoglycan.[14]
The Austrian pharmaceutical company, Biochemie, was founded inKundl in July 1946 at the site of a derelict brewery, at the suggestion of a French officer, Michel Rambaud (a chemist), who was able to obtain a small amount ofPenicillium start culture from France. Contamination of the fermentation tanks was a persistent problem and in 1951, the company biologist,Ernst Brandl, attempted to solve this by addingphenoxyethanol to the tanks as an anti-bacterial disinfectant. This resulted unexpectedly in an increase in penicillin production: but, the penicillin produced was not benzylpenicillin, but phenoxymethylpenicillin. Phenoxyethanol was fermented tophenoxyacetic acid[16] in the tanks, which was then incorporated into penicillin via biosynthesis. Importantly, Brandl realised that phenoxymethylpenicillin is not destroyed by stomach acid and can therefore be given by mouth. Phenoxymethyl penicillin was originally discovered by Eli Lilly in 1948 as part of their efforts to study penicillin precursors, but was not further exploited, and there is no evidence that Lilly understood the significance of their discovery at the time.[5]: 119–121 [17]
Biochemie is part ofSandoz.[citation needed]
There were four named penicillins at the time penicillin V was discovered (penicillins I, II, III, IV), however, Penicillin V was named "V" forVertraulich (German forconfidential);[5]: 121 it was not named for the Roman numeral "5".Penicillin VK is thepotassium salt of penicillin V (K is the chemical symbol for potassium).[citation needed]
fenoksymetylpenicillin
