Benzylpenicillin potassiumProduct ingredient for Benzylpenicillin

Name
Benzylpenicillin potassium
Drug Entry
Benzylpenicillin

Benzylpenicillin (Penicillin G) is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms.

Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.

Accession Number
DBSALT002390
Structure
Thumb
Synonyms
6β-phenylacetamidopenicillanic acid potassium salt / benzylpenicillin potassium salt / benzylpénicilline potassique / penicillin G K / penicillin G potassium / Potassium benzylpenicillin / Potassium benzylpenicillinate / Potassium penicillin G / potassium salt of benzylpenicillin
UNII
VL775ZTH4C
CAS Number
113-98-4
Weight
Average: 372.48
Monoisotopic: 372.0546097
Chemical Formula
C16H17KN2O4S
InChI Key
IYNDLOXRXUOGIU-LQDWTQKMSA-M
InChI
InChI=1S/C16H18N2O4S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/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-phenylacetamido)-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)CC1=CC=CC=C1)C([O-])=O
KEGG Drug
D01053
ChemSpider
391379
ChEBI
7963
ChEMBL
CHEMBL1223
Wikipedia
Benzylpenicillin
Predicted Properties
PropertyValueSource
Water Solubility0.35 mg/mLALOGPS
logP1.45ALOGPS
logP1.08ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.54 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.36 m3·mol-1ChemAxon
Polarizability33.44 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon