Phenoxymethylpenicillin

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Phenoxymethylpenicillin (Penicillin V)
Penicillin-V-2D-skeletal.png
Phenoxymethylpenicillin ball-and-stick.png
Systematic (IUPAC) name
3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names Veetids
AHFS/Drugs.com monograph
MedlinePlus a685015
Licence data US Daily Med:link
Pregnancy cat. B (US)
Legal status Prescription only
Routes oral as the potassium salt
Pharmacokinetic data
Bioavailability 60%
Protein binding 80%
Metabolism hepatic
Half-life 30–60 min
Excretion renal
Identifiers
CAS number 87-08-1 YesY , 132-98-9 (potassium), 147-48-8 (anhydrous calcium), 73368-74-8 (calcium dihydrate)
ATC code J01CE02
PubChem CID 6869
DrugBank DB00417
ChemSpider 6607 YesY
UNII Z61I075U2W YesY
KEGG D05411 YesY
ChEBI CHEBI:27446 YesY
ChEMBL CHEMBL615 YesY
Chemical data
Formula C16H18N2O5S 
Mol. mass 350.39 g/mol
 YesY (what is this?)  (verify)

Phenoxymethylpenicillin, commonly known as penicillin V, is an antibiotic useful for the treatment of a number of bacterial infections. It is a penicillin that is orally active. It is less active than benzylpenicillin (penicillin G) against Gram-negative bacteria.[1][2] Phenoxymethylpenicillin is more acid-stable than benzylpenicillin, which allows it to be given orally. 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. It is not active against beta-lactamase-producing bacteria, which include many strains of Staphylococci.[3]

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.[1][2]

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.[3] Patients treated initially with parenteral benzylpenicillin may continue oral treatment with phenoxymethylpenicillin once a satisfactory clinical response has been obtained.[4]

For prophylaxis against rheumatic fever, phenoxymethylpenicillin given by mouth twice a day is used as an alternative to injections of benzathine penicillin given every two weeks. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[5]

Medical uses[edit]

Specific indications for phenoxymethylpenicillin include:[4][6]

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

Adverse effects[edit]

Further information: Penicillin drug reaction

Phenoxymethylpenicillin is usually well tolerated but may occasionally cause transient nausea, vomiting, epigastric distress, diarrhea, and black hairy tongue. A previous hypersensitivity reaction to any penicillin is a contraindication.[3][4]

Compendial status[edit]

References[edit]

  1. ^ a b Garrod, L. P. (1960). "Relative Antibacterial Activity of Three Penicillins". British Medical Journal (5172): 527–29. 
  2. ^ a b Garrod, L. P. (1960). "The Relative Antibacterial Activity of Four Penicillins". British Medical Journal (5214): 1695–6. 
  3. ^ a b c "Penicillin V Potassium tablet: Drug Label Sections". U.S. National Library of Medicine, Daily Med: Current Medication Information. December 2006. Retrieved 2009-08-02. 
  4. ^ 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. 
  5. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  6. ^ Rossi S., ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3. 
  7. ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)". Retrieved 26 March 2010.