Benzylpenicillin sodiumProduct ingredient for Benzylpenicillin
- Name
- Benzylpenicillin sodium
- 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
- DBSALT000726
- Structure
Structure for Benzylpenicillin sodium (DBSALT000726)
- Synonyms
- American penicillin / benzylpenicillin sodium salt / benzylpenicillinic acid sodium salt / monosodium benzylpenicillin / penicillin G sodium / sodium benzylpenicillinate / sodium penicillin G
- UNII
- YS5LY7JF4N
- CAS Number
- 69-57-8
- Weight
- Average: 356.37
Monoisotopic: 356.08067249 - Chemical Formula
- C16H17N2NaO4S
- InChI Key
- FCPVYOBCFFNJFS-LQDWTQKMSA-M
- InChI
- InChI=1S/C16H18N2O4S.Na/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
- sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
- SMILES
- [Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C([O-])=O
- External Links
- PubChem Compound
- 23668834
- ChemSpider
- 6014
- ChEBI
- 51765
- ChEMBL
- CHEMBL1126
- Wikipedia
- Benzylpenicillin
- Predicted Properties
Property Value Source Water Solubility 0.329 mg/mL ALOGPS logP 1.46 ALOGPS logP 1.08 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 3.53 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 89.54 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 95.36 m3·mol-1 Chemaxon Polarizability 33.44 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon