Compound ID | 457

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LY186826 (derived from LY173013)

Class: Beta-lactam (cephalosporin)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Their mechanism of action was found to be similar to β-lactams. The structure of this antibiotic allows strong binding to penicillin binding proteins (PBPs), especially PBP2 (2)
Description: Pyrazolidinone containing compound
Institute where first reported: Eli Lilly, US
Year first mentioned: 1986
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Superseded by later compounds such as LY193239 which demonstrated higher potency through affinity for PBP enzymes (2)
Chemical structure(s):
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Molecular weight: 408.39
Iso. SMILES: CC(=O)C1=C(N2C(=O)C(CN2C1)NC(=O)/C(=N/OC)/C3=CSC(=N3)N)C(=O)O
InChI Key: IZZDXJHOVYWBDZ-VXLYETTFSA-N
Can. SMILES: CC(=O)C1=C(C(=O)O)N2C(=O)C(CN2C1)NC(=O)/C(=N/OC)/C3=CSC(=N3)N
InChI: InChI=1S/C15H16N6O6S/c1-6(22)7-3-20-4-8(13(24)21(20)11(7)14(25)26)17-12(23)10(19-27-2)9-5-28-15(16)18-9/h5,8H,3-4H2,1-2H3,(H2,16,18)(H,17,23)(H,25,26)/b19-10+
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6918048
Citations:
  • http://pubs.acs.org/doi/pdf/10.1021/jo00227a013
  • https://books.google.co.uk/books?id=GgPoCAAAQBAJ&pg=PA308&lpg=PA308&dq=LY173013&source=bl&ots=spuNwNoFKJ&sig=jTjiVJirHIj6GLgqaVt76y91ThA&hl=en&sa=X&ei=4ct2Vc6bLMOBU_e3gHA&ved=0CDcQ6AEwBg#v=onepage&q=LY173013&f=false
  • https://www.jstage.jst.go.jp/article/antibiotics1968/43/1/43_1_92/_pdf/-char/en

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