Compound ID | 1922

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Penicillin V

Synonym(s): Phenoxymethylpenicillin  |  Penicillin VK

Class: Beta-lactam

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. D-ala-D-ala carboxypeptidase inhibitor; penicillin-binding protein (PBP) inhibitor; prevents cross-linking of bacterial cell wall; susceptible to penicillinases produced by staphylococci
Target Pathogen: Active against streptococci, staphylococci, and enterococci
Description: Natural product from Penicillium chrysogenum (formerly Penicillium notatum); contains a 6-aminopenicillanic acid nucleus and a 6-beta-(phenoxyacetyl)amino; developed for oral use
Year first mentioned: 1948
Highest development stage: Approved by FDA in 1958
Development status: Approved
Reason dropped: Several formulations have been discontinued
Chemical structure(s):
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Molecular weight: 350.39
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
InChI Key: BPLBGHOLXOTWMN-MBNYWOFBSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)COC3=CC=CC=C3
InChI: InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/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/6869
Guide to Pharmacology: phenoxymethylpenicillin
Citations:
  • https://adc.bmj.com/content/105/11/1118.long
  • https://www.bmj.com/content/1/4965/496
  • https://doi.org/10.1111/j.2042-7158.1955.tb12082.x
  • https://doi.org/10.1111/j.2042-7158.1956.tb12127.x
  • https://doi.org/10.1111/j.2042-7158.1955.tb12081.x

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