Compound ID | 1864

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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):
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Molecular weight: 420.51
Iso. 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 Key: AVAACINZEOAHHE-VFZPANTDSA-N
Can. 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
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/73303
Guide to Pharmacology: doripenem
Citations:
  • https://pubs.acs.org/doi/10.1021/op034088n
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2730083/

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