Phenoxymethylpenicillin
| File:Penicillin-V-2D-skeletal.png | |
| 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 | |
| Clinical data | |
| [[Regulation of therapeutic goods |Template:Engvar data]] | |
| Pregnancy category |
|
| Routes of administration | enteral |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Bioavailability | 60% |
| Protein binding | 80% |
| Metabolism | hepatic |
| Biological half-life | 30–60 min |
| Excretion | renal |
| Identifiers | |
| CAS Number | 87-08-01 , 132-98-9 (potassium), 147-48-8 (anhydrous calcium), 73368-74-8 (calcium dihydrate) |
| ATC code | J01CE02 |
| PubChem | CID 6869 |
| DrugBank | DB00417 |
| Chemical data | |
| Formula | C16H18N2O5S |
| Molar mass | 350.39 g/mol[[Script error: No such module "String".]] |
| Script error: No such module "collapsible list". | |
Phenoxymethylpenicillin, commonly known as penicillin V, is the orally active form of penicillin, an antibiotic. 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 penicillin sensitive 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]
Contents
Indications
Specific indications for phenoxymethylpenicillin include:[2][3]
- Infections caused by Streptococcus pyogenes
- Tonsillitis
- Pharyngitis
- Skin infections
- Anthrax (mild uncomplicated infections)
- Lyme disease (early stage in pregnant women or young children)
- Pharyngitis or tonsillitis
- Rheumatic fever (primary and secondary prophylaxis)
- Streptococcal skin infections
- Spleen disorders (pneumococcal infection prophylaxis)
- Moderate-to-severe gingivitis (with metronidazole)
- Avulsion injuries of teeth (as an alternative to Tetracycline)
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]
Toxicology
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Compendial status
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References
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da:Phenoxymethylpenicillines:Fenoximetilpenicilina fr:PénicillineV hr:Fenoksimetilpenicilin it:Fenossimetilpenicillina pl:Fenoksymetylopenicylina sl:Fenoksimetilpenicilin sv:Fenoximetylpenicillin
zh:青霉素V钾- ↑ 1.0 1.1 1.2 1.3 "Penicillin V Potassium tablet: Drug Label Sections". U.S. National Library of Medicine, Daily Med: Current Medication Information. 12/2006. Retrieved 2009-08-02. Check date values in:
|date=(help) - ↑ 2.0 2.1 2.2 2.3 Sweetman S., ed. (2002). Martindale: The complete drug reference (Electronic version ed.). London: Royal Pharmaceutical Society of Great Britain and the Pharmaceutical Press.
- ↑ Rossi S., ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3.
- ↑ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Retrieved 26 March 2010.
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