Phenoxymethylpenicillin, also known as penicillin V (PcV) and penicillin VK, is an antibiotic useful for the treatment of a number of

bacterial infections Pathogenic bacteria are bacteria that can cause disease. This article focuses on the bacteria that are pathogenic to humans. Most species of bacteria are harmless and are often beneficial but others can cause infectious diseases. The number of t ...

. Specifically it is used for the treatment of

strep throat Streptococcal pharyngitis, also known as streptococcal sore throat (strep throat), is pharyngitis (an infection of the pharynx, the back of the throat) caused by ''Streptococcus pyogenes'' a gram-positive, group A streptococcus. Common sympto ...

otitis media Otitis media is a group of inflammatory diseases of the middle ear. One of the two main types is acute otitis media (AOM), an infection of rapid onset that usually presents with ear pain. In young children this may result in pulling at the ear, ...

, and

cellulitis Cellulitis is usually a bacterial infection involving the inner layers of the skin. It specifically affects the dermis and subcutaneous fat. Signs and symptoms include an area of redness which increases in size over a few days. The borders of ...

. 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 Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin w ...

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...

, and

allergic reaction Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic derma ...

s including

anaphylaxis Anaphylaxis is a serious, potentially fatal allergic reaction and medical emergency that is rapid in onset and requires immediate medical attention regardless of use of emergency medication on site. It typically causes more than one of the foll ...

. It is not recommended in those with a history of

penicillin allergy The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are ...

. It is relatively safe for use during

pregnancy Pregnancy is the time during which one or more offspring develops (gestation, gestates) inside a woman, woman's uterus (womb). A multiple birth, multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occur ...

. It is in the penicillin and

beta lactam A beta-lactam (β-lactam) ring is a four-membered lactam. A ''lactam'' is a cyclic amide, and ''beta''-lactams are named so because the nitrogen atom is attached to the β-carbon atom relative to the carbonyl. The simplest β-lactam possible is ...

family of medications. It usually results in bacterial death. Phenoxymethylpenicillin was first made in 1948 by

Eli Lilly Eli Lilly (July 8, 1838 – June 6, 1898) was an American soldier, pharmacist, chemist, and businessman who founded the Eli Lilly and Company pharmaceutical corporation. Lilly enlisted in the Union Army during the American Civil War and ...

. It is on the

World Health Organization's List of Essential Medicines The WHO Model List of Essential Medicines (aka Essential Medicines List or EML), published by the World Health Organization (WHO), contains the medications considered to be most effective and safe to meet the most important needs in a health s ...

. It is available as a generic medication. In 2020, it was the 319th most commonly prescribed medication in the United States, with more than 900thousand prescriptions.

Medical uses

Specific uses for phenoxymethylpenicillin include: * Infections caused by ''

Streptococcus pyogenes ''Streptococcus pyogenes'' is a species of Gram-positive, aerotolerant bacteria in the genus '' Streptococcus''. These bacteria are extracellular, and made up of non-motile and non-sporing cocci (round cells) that tend to link in chains. They ...

'' **

Tonsillitis Tonsillitis is inflammation of the tonsils in the upper part of the throat. It can be acute or chronic. Acute tonsillitis typically has a rapid onset. Symptoms may include sore throat, fever, enlargement of the tonsils, trouble swallowing, and en ...

Pharyngitis Pharyngitis is inflammation of the back of the throat, known as the pharynx. It typically results in a sore throat and fever. Other symptoms may include a Rhinorrhea, runny nose, cough, headache, difficulty swallowing, swollen lymph nodes, and a ...

Skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different de ...

infections * Anthrax (mild uncomplicated infections) *

Lyme disease Lyme disease, also known as Lyme borreliosis, is a vector-borne disease caused by the ''Borrelia'' bacterium, which is spread by ticks in the genus ''Ixodes''. The most common sign of infection is an expanding red rash, known as erythema migran ...

(early stage in pregnant women or young children) * Rheumatic fever (primary and secondary prophylaxis) * Streptococcus, Streptococcal skin infections * Spleen#Disorders, 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 Wiktionary:odontogenic, 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 (pharmacokinetics), absorption can be unpredictable. Except for the treatment or prevention of infection with ''

'' (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. It is not active against beta-lactamase-producing bacteria, which include many strains of ''staphylococcus, Staphylococci''.

Adverse effects

Phenoxymethylpenicillin is usually well tolerated but may occasionally cause transient

, vomiting, epigastric distress,

, constipation, acidic smell to urine and black hairy tongue. A previous hypersensitivity, hypersensitivity reaction to ''any'' penicillin is a contraindication.

Mechanism of action

The mechanism of phenoxymethylpenicillin is identical to that of all other penicillins. It exerts a Bactericidal#Bactericidal antibiotics, bactericidal action against penicillin-sensitive microorganisms during the stage of active multiplication. It acts by enzyme inhibitor, inhibiting the protein biosynthesis, biosynthesis of cell-wall peptidoglycan.

Compendial status

* British Pharmacopoeia

History

The Austrian pharmaceutical company, Biochemie, was founded in Kundl 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 of ''Penicillium'' 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 adding phenoxyethanol 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 to phenoxyacetic acid 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. Biochemie is now part of Novartis#Sandoz, Sandoz.

Names

There were four named penicillins at the time penicillin V was discovered (Penicillin#Nomenclature, penicillins I, II, III, IV), however, Penicillin V was named "V" for ''Vertraulich'' (confidential); it was not named for the Roman numeral "5". Penicillin VK is the potassium salt of penicillin V (K is the chemical symbol for potassium).

References

External links

* {{portal bar, Medicine Penicillins Enantiopure drugs World Health Organization essential medicines Wikipedia medicine articles ready to translate