Compound ID | 1915

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Latamoxef

Synonym(s): Moxalactam  |  Moxam  |  LY127935  |  LY-127935  |  LY 127935  |  6059-S

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds to bacterial penicillin-binding proteins (PBP); PBP inhibitor
Target Pathogen: Primarily Enterobacteriaceae: Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Enterobacter spp., Citrobacter spp., Serratia marcescens, Salmonella spp., Shigella spp., and weaker/moderate activity against Streptococcus pneumoniae, Streptococcus pyogenes, other streptococci and some Staphylococcus aureus
Propensity to select resistant mutants: Low–Moderate initially; increasing due to ESBLs and β-lactamases
Description: Semisynthetic Cephalosporine (oxacephem), derived from Cephalosporin C
Institute where first reported: Shionogi and Co., Ltd.
Year first mentioned: 1977
Highest development stage: Withdrawn
Development status: Approved
Reason dropped: Prolonged bleeding time
Chemical structure(s):
Click here for structure editor
Molecular weight: 520.47
Iso. SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)C(C4=CC=C(C=C4)O)C(=O)O)OC)OC2)C(=O)O
InChI Key: JWCSIUVGFCSJCK-CAVRMKNVSA-N
Can. SMILES: CN1C(=NN=N1)SCC2=C(C(=O)O)N3C(=O)[C@]([C@H]3OC2)(NC(=O)C(C4=CC=C(C=C4)O)C(=O)O)OC
InChI: InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/47499
Guide to Pharmacology: latamoxef
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/3778044/
  • https://pubmed.ncbi.nlm.nih.gov/6354685/
    • Patent: DE2713370A1

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