Compound ID | 1923

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Penicillin G

Synonym(s): Benzylpenicillin

Class: Beta-lactam (penicillin)

Spectrum of activity: Gram-positive
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria, but vulnerable to penicillinases produced by staphylococci
Description: Natural compound. Parenteral application
Year first mentioned: 1938
Highest developmental phase: Approved by FDA in 1951
Development status: Approved
Chemical structure(s):
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Molecular weight: 334.39
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
InChI Key: JGSARLDLIJGVTE-MBNYWOFBSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)CC3=CC=CC=C3
InChI: InChI=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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5904
Guide to Pharmacology: penicillin G
Citations:
  • https://academic.oup.com/jac/article/41/6/589/665224?login=false
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2048009/
  • https://www.sciencedirect.com/science/article/pii/S0140673601087281?ref=pdf_download&fr=RR-2&rr=858e5db979860749
  • https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(01)08728-1/fulltext

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