Benzathine benzylpenicillinProduct ingredient for Benzylpenicillin
- Name
- Benzathine benzylpenicillin
- 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
- DBSALT002769
- Structure
Structure for Benzathine benzylpenicillin (DBSALT002769)
- Synonyms
- Benzathin penicillin G / Benzathine benzylpenicillin anhydrous / Benzathine benzylpenicilline / Penicillin G benzathine anhydrous
- UNII
- SSZ1S4I0US
- CAS Number
- 1538-09-6
- Weight
- Average: 909.13
Monoisotopic: 908.360105135 - Chemical Formula
- C48H56N6O8S2
- InChI Key
- BVGLIYRKPOITBQ-ANPZCEIESA-N
- InChI
- InChI=1S/2C16H18N2O4S.C16H20N2/c2*1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2/t2*11-,12+,14-;/m11./s1
- IUPAC Name
- bis((2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid); benzyl[2-(benzylamino)ethyl]amine
- SMILES
- C(CNCC1=CC=CC=C1)NCC1=CC=CC=C1.[H][C@@]1(NC(=O)CC2=CC=CC=C2)C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H].[H][C@@]1(NC(=O)CC2=CC=CC=C2)C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H]
- External Links
- ChemSpider
- 14498
- ChEBI
- 51352
- ChEMBL
- CHEMBL3182097
- Wikipedia
- Benzathine_benzylpenicillin
- Predicted Properties
Property Value Source Water Solubility 0.285 mg/mL ALOGPS logP 1.92 ALOGPS logP 1.08 Chemaxon logS -3.1 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 2 Chemaxon Polar Surface Area 86.71 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 84.53 m3·mol-1 Chemaxon Polarizability 33.54 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon