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):
Canonical 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
Isomeric 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:	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
InChI Key:	TYMABNNERDVXID-DLYFRVTGSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/72015

External links:
Guide to Pharmacology:	panipenem
Main Source:	https://pubmed.ncbi.nlm.nih.gov/6630055/
Citations:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC187661/ https://link.springer.com/article/10.2165/00003495-200363090-00005