Compound ID | 301

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Lenapenem

Synonym(s): BO-2727  |  BO 2727  |  BO2727

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against methicillin-resistant Staphylococcus aureus
Description: Carbapenem with (R)-1-hydroxy-3-(N-methylamino)propyl group; demonstrates high stability against DHP-1
Institute where first reported: Banyu; Merck and Co.
Year first mentioned: 1990
Highest development stage: Preclinical
Development status: Experimental
Chemical structure(s):
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Molecular weight: 399.51
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)[C@@H](CCNC)O)C(=O)O)[C@@H](C)O
InChI Key: PZLOCBSBEUDCPF-YJIVIRPOSA-N
Can. SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H]([C@@H](CCNC)O)NC3)C(=O)O
InChI: InChI=1S/C18H29N3O5S/c1-8-14-13(9(2)22)17(24)21(14)15(18(25)26)16(8)27-10-6-11(20-7-10)12(23)4-5-19-3/h8-14,19-20,22-23H,4-7H2,1-3H3,(H,25,26)/t8-,9-,10+,11+,12-,13-,14-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/216262
Guide to Pharmacology: lenapenem
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/9444403/
  • https://doi.org/10.7164/antibiotics.50.598

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