Benethamine penicillinProduct ingredient for Benzylpenicillin

Name
Benethamine penicillin
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
DBSALT002391
Structure
Synonyms
benethamine penicillin G / penicilina-benetamina / penicillin G benethamine
UNII
O3S7RWT8R5
CAS Number
751-84-8
Weight
Average: 545.7
Monoisotopic: 545.234827793
Chemical Formula
C31H35N3O4S
InChI Key
JAQPGQYDZJZOIN-LQDWTQKMSA-N
InChI
InChI=1S/C16H18N2O4S.C15H17N/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;1-3-7-14(8-4-1)11-12-16-13-15-9-5-2-6-10-15/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,16H,11-13H2/t11-,12+,14-;/m1./s1
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; benzyl(2-phenylethyl)amine
SMILES
C(CC1=CC=CC=C1)NCC1=CC=CC=C1.[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O
ChemSpider
58565
ChEBI
52151
ChEMBL
CHEMBL2107679
Predicted Properties
PropertyValueSource
Water Solubility0.285 mg/mLALOGPS
logP1.92ALOGPS
logP1.08Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.53Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area86.71 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity84.53 m3·mol-1Chemaxon
Polarizability33.5 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon