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Phenoxymethylpenicillin
Systematic (IUPAC) name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6- [(phenylacetyl)amino]- 4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylic acid
Identifiers
CAS number 87-08-01 , 132-98-9 (potassium), 147-48-8 (anhydrous calcium), 73368-74-8 (calcium dihydrate)
ATC code J01CE02
PubChem 6869
DrugBank DB00417
Chemical data
Formula C 16H18N2O5S 
Mol. mass 350.39 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 60%
Protein binding 80%
Metabolism hepatic
Half life 30 – 60 min
Excretion renal
Therapeutic considerations
Licence data

US Daily Med:link

Pregnancy cat. B(US)
Legal status Prescription only
Routes enteral

Phenoxymethylpenicillin, commonly known as penicillin V, is the orally active form of penicillin. It is less active than benzylpenicillin, however, and is appropriate only in conditions where high tissue concentrations are not required. Phenoxymethylpenicillin exerts a bactericidal action against penicillinsensitive microorganisms during the stage of active multiplication. It acts through the inhibition of biosynthesis of cell-wall Peptidoglycan. It is not active against the Beta-lactamase-producing bacteria, which include many strains of staphylococci.[1]

Phenoxymethylpenicillin has a range of antimicrobial activity similar to that of benzylpenicillin and a similar mode of action. It may be less active against some susceptible organisms, particularly Gram-negative bacteria. The mechanisms and patterns of resistance to phenoxymethylpenicillin are similar to those of benzylpenicillin.[1][2]

It is used only for the treatment of mild to moderate infections, and not for chronic, severe, or deep-seated infections since absorption can be unpredictable. Therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response.[1] Patients treated initially with parenteral benzylpenicillin may continue oral treatment with phenoxymethylpenicillin once a satisfactory clinical response has been obtained.[2]

Indications

Specific indications for phenoxymethylpenicillin include:[2][3]

Penicillin V is the first choice in the treatment of odontogenic infections.

Adverse Effects and Precautions

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.[1][2]

References

  1. ^ a b c d "Penicillin V Potassium tablet: Drug Label Sections". U.S. National Library of Medicine, Daily Med: Current Medication Information. 12/2006. http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=645. Retrieved 2009-08-02.  
  2. ^ a b c d Sweetman S., ed (2002). Martindale: The complete drug reference (Electronic version ed.). London: Royal Pharmaceutical Society of Great Britain and the Pharmaceutical Press.  
  3. ^ Rossi S., ed (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3.  
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