Phenoxymethylpenicillin

Phenoxymethylpenicillin, also known as penicillin V (PcV) 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.

Phenoxymethylpenicillin
Clinical data
Trade namesVeetids, Apocillin, others
Other namespenicillin phenoxymethyl, penicillin V, penicillin VK
AHFS/Drugs.comMonograph
MedlinePlusa685015
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60%
Protein binding80%
MetabolismLiver
Elimination half-life30–60 min
ExcretionkKidney
Identifiers
  • 3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.566
Chemical and physical data
FormulaC16H18N2O5S
Molar mass350.39 g·mol−1
3D model (JSmol)
Melting point120–128 °C (248–262 °F)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
  • 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
  (verify)

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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.