Phenoxymethylpenicillin

Phenoxymethylpenicillin
Clinical data
Trade namesVeetids, Apocillin,[1] 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
ExcretionKidney
Identifiers
IUPAC name
  • 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)
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
  (verify)

Phenoxymethylpenicillin, also known as penicillin V (PcV) and penicillin VK, is an antibiotic useful for the treatment of a number of bacterial infections.[2] Specifically it is used for the treatment of strep throat, otitis media, and cellulitis.[2] It is also used to prevent rheumatic fever and to prevent infections following removal of the spleen.[2] It is given by mouth.[2]

Side effects include diarrhea, nausea, and allergic reactions including anaphylaxis.[2] It is not recommended in those with a history of penicillin allergy.[2] It is relatively safe for use during pregnancy.[3] It is in the penicillin and beta lactam family of medications.[4] It usually results in bacterial death.[4]

Phenoxymethylpenicillin was first made in 1948 by Eli Lilly.[5]: 121  It is on the World Health Organization's List of Essential Medicines.[6] It is available as a generic medication.[4] In 2022, it was the 259th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[7][8]

  1. ^ "Apocillin". Felleskatalogen (in Norwegian). LMI (Legemiddelindustrien). Retrieved 23 June 2018. fenoksymetylpenicillin
  2. ^ a b c d e f World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. hdl:10665/44053. ISBN 9789241547659.
  3. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 95. ISBN 9781284057560.
  4. ^ a b c "Penicillin V". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  5. ^ Greenwood D (2008). "Wonder Drugs". Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. ISBN 978-0-19-953484-5. Archived from the original on 20 December 2016.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  8. ^ "PenicillinV Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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