Phenoxymethylpenicillin

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Phenoxymethylpenicillin
Penicillin-V-2D-skeletal.png
Phenoxymethylpenicillin ball-and-stick.png
Clinical data
Trade namesVeetids, Apocillin,[1] others
Synonymspenicillin phenoxymethyl, penicillin V, penicillin VK
AHFS/Drugs.comMonograph
MedlinePlusa685015
License data
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration
by mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60%
Protein binding80%
Metabolismliver
Elimination half-life30–60 min
Excretionkidney
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.001.566 Edit this at Wikidata
Chemical and physical data
FormulaC16H18N2O5S
Molar mass350.39 g·mol−1
3D model (JSmol)
Melting point120–128 °C (248–262 °F)
  (verify)

Phenoxymethylpenicillin, also known as penicillin V 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.[5] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[6] It is available as a generic medication.[4] The wholesale cost in the developing world is about US$0.05–0.96 per day.[7] In the United States a course of treatment costs less than $25.[3]

Medical uses[edit]

Specific indications for phenoxymethylpenicillin include:[8][9]

Penicillin V is sometimes used in the treatment of odontogenic infections.

It is less active than benzylpenicillin (penicillin G) against Gram-negative bacteria.[10][11] 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.[10][11]

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 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.[12] People treated initially with parenteral benzylpenicillin may continue treatment with phenoxymethylpenicillin by mouth once a satisfactory response has been obtained.[8]

It is not active against beta-lactamase-producing bacteria, which include many strains of Staphylococci.[12]

Adverse effects[edit]

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.[8][12]

Mechanism of action[edit]

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.

Compendial status[edit]

References[edit]

  1. ^ "Apocillin". Felleskatalogen (in Norwegian). LMI (Legemiddelindustrien). Archived from the original on 2017-03-16. Retrieved 2018-06-23. fenoksymetylpenicillin
  2. ^ a b c d e f WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. X. ISBN 9789241547659. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
  3. ^ a b Hamilton, Richart (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, David (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 121. ISBN 9780199534845. Archived from the original on 2016-12-20.
  6. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
  7. ^ "Penicillin, Phenoxymethyl". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  8. ^ a b c Sweetman S., ed. (2002). Martindale: The complete drug reference (Electronic version ed.). London: Royal Pharmaceutical Society of Great Britain and the Pharmaceutical Press.
  9. ^ Rossi S., ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3.
  10. ^ a b Garrod, L. P. (1960). "Relative Antibacterial Activity of Three Penicillins". British Medical Journal (5172): 527–29.
  11. ^ a b Garrod, L. P. (1960). "The Relative Antibacterial Activity of Four Penicillins". British Medical Journal (5214): 1695–6.
  12. ^ a b c "Penicillin V Potassium tablet: Drug Label Sections". U.S. National Library of Medicine, Daily Med: Current Medication Information. December 2006. Archived from the original on 2009-07-27. Retrieved 2009-08-02.
  13. ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 26 March 2010.