Doripenem

Synonym(s): S-4661

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. Similar to meropenem
Institute where first reported:	Shionogi Inc
Year first mentioned:	2003
Highest developmental phase:	Approved by FDA in 2007
Development status:	Discontinued
Reason Dropped:	In treating patients with pneumoniae, doripenem showed increased risk of death and lower clinical cure rates compared to imipenem and cilastatin for injection

Chemical structure(s):
Canonical SMILES:	C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](CNS(=O)(=O)N)NC3)C(=O)O
Isomeric SMILES:	C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O
InChI:	InChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1
InChI Key:	AVAACINZEOAHHE-VFZPANTDSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/73303

External links:
Guide to Pharmacology:	doripenem
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2730083/
Citation:	https://pubs.acs.org/doi/10.1021/op034088n