Compound ID | 1863

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Biapenem

Synonym(s): LJ C10,627

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) and interferes with bacterial cell wall integrity and synthesis; carbapenems bind to all PBPs, with PBP2 and PBP4 as the highest-affinity targets; carbapenems have a very broad spectrum including non-fermenters and are not hydrolysed by most beta-lactamases with exception of carbapenemases; PBP inhibitor
Description: Semisynthetic, derived from thienamycin. Similar to imipenem but more stable against human renal dehydropeptidase-I. Available in Japan, Thailand, China and India
Year first mentioned: 1995
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 350.39
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])[C@@H](C)O
InChI Key: MRMBZHPJVKCOMA-YJFSRANCSA-N
Can. SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-]
InChI: InChI=1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/71339
Guide to Pharmacology: biapenem
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/8354307/
  • https://pubmed.ncbi.nlm.nih.gov/8626267/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8944426/
  • https://pubmed.ncbi.nlm.nih.gov/12381221/

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