Phenoxymethylpenicillin

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.

Phenoxymethylpenicillin

Clinical data
Trade names	Veetids, Apocillin, others
Other names	penicillin phenoxymethyl, penicillin V, penicillin VK
AHFS/Drugs.com	Monograph
MedlinePlus	a685015
License data	US DailyMed: Penicillin V
Routes of administration	By mouth
ATC code	J01CE02 (WHO)
Legal status
Legal status	US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	60%
Protein binding	80%
Metabolism	Liver
Elimination half-life	30–60 min
Excretion	Kidney
Identifiers
IUPAC name 3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number	87-08-1 Y 132-98-9 (potassium), 147-48-8 (anhydrous calcium), 73368-74-8 (calcium dihydrate)
PubChem CID	6869
DrugBank	DB00417 Y
ChemSpider	6607 Y
UNII	Z61I075U2W
KEGG	D05411 Y
ChEBI	CHEBI:27446 Y
ChEMBL	ChEMBL615 Y
CompTox Dashboard (EPA)	DTXSID3023429
ECHA InfoCard	100.001.566
Chemical and physical data
Formula	C16H18N2O5S
Molar mass	350.39 g·mol−1
3D model (JSmol)	Interactive image
Melting point	120–128 °C (248–262 °F)
SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
InChI InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1 Y Key:BPLBGHOLXOTWMN-MBNYWOFBSA-N Y
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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 by Eli Lilly.^: 121 It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 256th most commonly prescribed medication in the United States, with more than 1 million prescriptions.

Specific uses for phenoxymethylpenicillin include:

• Infections caused by Streptococcus pyogenes
  • Tonsillitis
  • Pharyngitis
  • Skin infections
• 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.^{[citation needed]}

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.^{[citation needed]}

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.

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

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.

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

• British Pharmacopoeia

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.^{: 119–121}

Biochemie is part of Sandoz.^{[citation needed]}

Names

There were four named penicillins at the time penicillin V was discovered (penicillins I, II, III, IV), however, Penicillin V was named "V" for Vertraulich (German for confidential);^: 121 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).^{[citation needed]}