Chemical Component Summary

NamePENICILLIN G
Identifiers(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylethanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
FormulaC16 H18 N2 O4 S
Molecular Weight334.39
TypeNON-POLYMER
Isomeric SMILESCC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
InChIInChI=1S/C16H18N2O4S/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)/t11-,12+,14-/m1/s1
InChIKeyJGSARLDLIJGVTE-MBNYWOFBSA-N

Chemical Details

Formal Charge0
Atom Count41
Chiral Atom Count3
Bond Count43
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB01053 
NameBenzylpenicillin
Groups
  • vet_approved
  • approved
DescriptionBenzylpenicillin (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.
Synonyms
  • Benzylpenicillin sodium
  • Benzathine benzylpenicillin
  • Penicillin G
  • Free penicillin II
  • 6-(2-phenylacetamido)penicillanic acid
Brand Names
  • Megacillin 500 Sus
  • Crystapen 10000000 Iu Pws
  • Penicillin G Na for Inj USP 1000000u/vial
  • Crystapen 10m I.U.
  • Penicillin G Sod. for Inj. (10millioniu) USP
IndicationFor use in the treatment of severe infections caused by penicillin G-susceptible microorganisms when rapid and high penicillin levels are required such as in the treatment of septicemia, meningitis, pericarditis, endocarditis and severe pneumonia.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • J01CR50
  • J01CE01
  • S01AA14
  • J01CE08
CAS number61-33-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 3MLKRLKEKSNDEIVQNTINKRINFIFGVIIFIFAVLVLRLGYLQIAQGSH...unknowninhibitor
Solute carrier family 22 member 8MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...unknownsubstrate,inhibitor
Solute carrier family 15 member 1MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...unknownsubstrate,inhibitor
Solute carrier family 15 member 2MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...unknowninhibitor
Beta-lactamase TEMMSIQHFRVALIPFFAAFCLPVFAHPETLVKVKDAEDQLGARVGYIELDLN...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5904
ChEMBL CHEMBL29
ChEBI CHEBI:18208