Compound ID | 1861

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Imipenem

Synonym(s): MK0787  |  N-Formimidoylthienamycin

Class: Beta-lactam (carbapenem)

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: 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 incl. non-fermenters and are not hydrolysed by most beta-lactamases with exception of carbapenemases
Description: Semisynthetic, derived from thienamycin, combined with cilastatin to prevent degradation of imipenem by the renal enzyme dehydropeptidase 1. Combination of imipenem/cilastatin and relebactam
Institute where first reported: MSAD Merck Co
Year first mentioned: 1977
Highest developmental phase: Approved by FDA in 2019
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 299.35
Iso. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
InChI Key: ZSKVGTPCRGIANV-ZXFLCMHBSA-N
Can. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(C(=O)O)N2C1=O)SCCN=CN)O
InChI: InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/104838
Guide to Pharmacology: imipenem
Citations:
  • https://academic.oup.com/jac/article/67/12/2793/774353?login=false
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3195018/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC283902/

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