Phenoxymethylpenicillin potassiumProduct ingredient for Phenoxymethylpenicillin

Name
Phenoxymethylpenicillin potassium
Drug Entry
Phenoxymethylpenicillin

Phenoxymethylpenicillin is a narrow spectrum antibiotic also commonly referred to as Penicillin V or Penicillin VK.3 It is a phenoxymethyl analog of Penicillin G, or benzylpenicillin. An orally active naturally penicillin, phenoxymethylpenicillin is used to treat mild to moderate infections in the respiratory tract, skin, and soft tissues caused by penicillin G­-sensitive microorganisms. Phenoxymethylpenicillin has also be used in some cases as prophylaxis against susceptible organisms. While there have been no controlled clinical efficacy studies that were conducted, phenoxymethylpenicillin has been suggested by the American Heart Association and the American Dental Association for use as an oral regimen for prophylaxis against bacterial endocarditis in patients with congenital heart disease or rheumatic or other acquired valvular heart disease when they undergo dental procedures and surgical procedures of the upper respiratory tract, except for those who are at an elevated risk for endocarditis.Label

Accession Number
DBSALT000299
Structure
Synonyms
Penicillin V potassium / Penicillin vk
UNII
146T0TU1JB
CAS Number
132-98-9
Weight
Average: 388.48
Monoisotopic: 388.04952432
Chemical Formula
C16H17KN2O5S
InChI Key
HCTVWSOKIJULET-LQDWTQKMSA-M
InChI
InChI=1S/C16H18N2O5S.K/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);/q;+1/p-1/t11-,12+,14-;/m1./s1
IUPAC Name
potassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
[K+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)COC1=CC=CC=C1)C([O-])=O
KEGG Drug
D00497
PubChem Compound
6869
ChemSpider
8286
ChEBI
7967
ChEMBL
CHEMBL1200852
Wikipedia
Phenoxymethylpenicillin
Predicted Properties
PropertyValueSource
Water Solubility0.636 mg/mLALOGPS
logP1.47ALOGPS
logP0.76Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.39Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area98.77 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity96.61 m3·mol-1Chemaxon
Polarizability33.89 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon