Compound ID | 348

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Cefetecol (GR69153)

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Enterobacteriaceae
Institute where first reported: GSK, USA
Year first mentioned: 1989
Highest development stage: Phase 1
Development status: Inactive
Reason dropped: Potent in vitro activity did not translate to good in vivo efficacy; catechol-containing compounds: MIC50s 0.008-0.39 mg/L against P. aeruginosa are superior to that of ceftazidime. These catecholic beta-lactams were expected to show superior therapeutic responses against pseudomonal infections in humans, but they were discontinued due to side effects or unfavourable pharmacokinetics in phase I/ II studies
Chemical structure(s):
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Molecular weight: 535.51
Iso. SMILES: C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=N\O[C@@H](C3=CC(=C(C=C3)O)O)C(=O)O)/C4=CSC(=N4)N)C(=O)O
InChI Key: ILZCDOYRDFDUPN-XUQRFURESA-N
Can. SMILES: C1=C(C=C(C(=C1)O)O)[C@@H](C(=O)O)O/N=C(/C2=CSC(=N2)N)\C(=O)N[C@@H]3C(=O)N4C(=CCS[C@H]34)C(=O)O
InChI: InChI=1S/C20H17N5O9S2/c21-20-22-8(6-36-20)12(24-34-14(19(32)33)7-1-2-10(26)11(27)5-7)15(28)23-13-16(29)25-9(18(30)31)3-4-35-17(13)25/h1-3,5-6,13-14,17,26-27H,4H2,(H2,21,22)(H,23,28)(H,30,31)(H,32,33)/b24-12-/t13-,14+,17-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9807169
Guide to Pharmacology: cefetecol
Citations:
  • http://aac.asm.org/content/35/5/929.long
  • http://www.sciencedirect.com/science/article/pii/S1341321X96714629

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