Compound ID | 1867

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Panipenem

Synonym(s): RS-533

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, closely related to imipenem. Combined with betamipron to prevent degradation of panipenem by the renal enzyme dehydropeptidase 1; available in Japan
Institute where first reported: Sankyo Co
Year first mentioned: 1982
Highest developmental phase: Approved (not in US)
Development status: Approved, off-patent
Chemical structure(s):
Click here for structure editor
Molecular weight: 339.41
Iso. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)S[C@H]3CCN(C3)C(=N)C)O
InChI Key: TYMABNNERDVXID-DLYFRVTGSA-N
Can. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(C(=O)O)N2C1=O)S[C@H]3CCN(C3)C(=N)C)O
InChI: InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/72015
Guide to Pharmacology: panipenem
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC187661/
  • https://link.springer.com/article/10.2165/00003495-200363090-00005
  • https://pubmed.ncbi.nlm.nih.gov/6630055/

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