Compound ID | 2765

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Thienamycin

Class: Beta-lactam

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Broad-spectrum activity (most active against Gram-positive cocci, Escherichia coli, Klebsiella pneumoniae, and Enterobacter sp.); cell wall synthesis inhibitor
Description: Natural product from Streptomyces cattleya; progenitor of N-formimidoyl thienamycin (MK0787; imipenem)
Institute where first reported: Merck Institute for Therapeutic Research, Merck Sharp & Dohme Research Laboratories Rahway, New Jersey, U.S.A. 07065; Compania Espanola de ]a Penicilina y Antibioticos S. A., Madrid, Spain
Year first mentioned: 1979
Development status: Inactive
Reason Dropped: Compound has pharmaceutical limitations (i.e. only active in narrow pH range, temperature, and concentration)
Chemical structure(s):
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Molecular weight: 272.32
Iso. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN)O
InChI Key: WKDDRNSBRWANNC-ATRFCDNQSA-N
Can. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(C(=O)O)N2C1=O)SCCN)O
InChI: InChI=1S/C11H16N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h5-6,8,14H,2-4,12H2,1H3,(H,16,17)/t5-,6-,8-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/441128
Citations:
  • https://link.springer.com/article/10.1007/BF01640839
  • https://pubmed.ncbi.nlm.nih.gov/761989/

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