Compound ID | 392

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Ritipenem

Synonym(s): FCE 22101

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Broad spectrum activity except against Pseudomonas aeruginosa
Description: Intravenous forms and oral form (Ritipenem acoxyl, FCE-22891, prodrug of ritipenem)
Institute where first reported: Novartis, Switzerland
Year first mentioned: 1986
Highest development stage: Phase 3
Development status: Inactive
Reason dropped: FDA withdrew approval in 2008; high neurotoxicity
Chemical structure(s):
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Molecular weight: 288.28
Iso. SMILES: C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)COC(=O)N)C(=O)O)O
InChI Key: IKQNRQOUOZJHTR-UWBRJAPDSA-N
Can. SMILES: C[C@H]([C@H]1C(=O)N2C(=C(COC(=O)N)S[C@H]12)C(=O)O)O
InChI: InChI=1S/C10H12N2O6S/c1-3(13)5-7(14)12-6(9(15)16)4(19-8(5)12)2-18-10(11)17/h3,5,8,13H,2H2,1H3,(H2,11,17)(H,15,16)/t3-,5+,8-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/65633
Guide to Pharmacology: ritipenem
Citations:
  • http://jac.oxfordjournals.org/content/20/2/179.full.pdf
  • http://jac.oxfordjournals.org/content/25/3/371.long
  • https://doi.org/10.1093/jac/23.suppl_c.1
  • https://doi.org/10.1093/jac/16.3.305

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