Compound ID | 357

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Cefluprenam

Synonym(s): E1077  |  E-1077  |  E 1077

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Broad spectrum activity
Description: Parenteral cephalosporin
Institute where first reported: Eisai Co Ltd, Japan
Year first mentioned: 1991
Highest development stage: Phase 3
Development status: Inactive
Reason dropped: Cephalosporins with a quaternary nitrogen such as E-1077 interfere with carnitine metabolism (1).
Chemical structure(s):
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Molecular weight: 556.59
Iso. SMILES: CC[N+](C)(C/C=C/C1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCF)/C3=NSC(=N3)N)SC1)C(=O)[O-])CC(=O)N
InChI Key: XAKKNLNAJBNLPC-MAYKBZFQSA-N
Can. SMILES: CC[N+](C)(C/C=C/C1=C(C(=O)[O-])N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N\OCF)/C3=NSC(=N3)N)CC(=O)N
InChI: InChI=1S/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6536774
Guide to Pharmacology: cefluprenam
Citation: https://journals.asm.org/doi/10.1128/aac.36.9.1894

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