Phenoxymethylpenicillin

Penicillin V

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	enteral
Pharmacokinetic data
Bioavailability	60%
Protein binding	80%
Metabolism	hepatic
Half-life	30–60 min
Excretion	renal
Identifiers
CAS number	87-08-1 Y , 132-98-9 (potassium), 147-48-8 (anhydrous calcium), 73368-74-8 (calcium dihydrate)
ATC code	J01CE02
PubChem	CID 6869
DrugBank	DB00417
ChemSpider	6607 N
UNII	Z61I075U2W N
KEGG	D05411 Y
ChEBI	CHEBI:27446 N
ChEMBL	CHEMBL615 N
Chemical data
Formula	C16H18N2O5S
Mol. mass	350.39 g/mol
SMILES	eMolecules & PubChem
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 N Key:BPLBGHOLXOTWMN-MBNYWOFBSA-N N
N(what is this?)  (verify)

Phenoxymethylpenicillin, commonly known as penicillin V, is a penicillin antibiotic 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 orally twice a day is used as an alternative to injections of benzathine penicillin given every two weeks.

Medical uses

Specific indications for phenoxymethylpenicillin include:^[4][5]

• 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 sometimes used 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.^[3][4]

Compendial status

• British Pharmacopoeia ^[6]

References

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. 12/2006. http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=645. 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. ^ Rossi S., ed (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook Pty Ltd. ISBN 0-9757919-2-3. 
6. ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 26 March 2010. 

See also

• Drug allergy