Compound ID | 412

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Ro 23-9424

Class: Beta-lactam; fluoroquinolone

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Acts initially as a cell wall synthesis inhibitor then as DNA synthesis inhibitor upon release of quinolone moiety during compound decomposition
Combined with other compounds: It is a codrug of fleroxacin and desacetylcefoaxime
Description: Semisynthetic compound composed of cephalosporin (desacetylcefotaxime) linked to a quinolone (fleroxacin); developed as a potential candidate for treatment of pneumococcal meningitis
Institute where first reported: Hoffmann-La Roche Inc, Switzerland
Year first mentioned: 1988
Highest development stage: Phase 2
Development status: Inactive
Chemical structure(s):
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Molecular weight: 764.76
Iso. SMILES: CN1CCN(CC1)C2=C(C=C3C(=C2F)N(C=C(C3=O)C(=O)OCC4=C(N5[C@@H]([C@@H](C5=O)NC(=O)/C(=N\OC)/C6=CSC(=N6)N)SC4)C(=O)O)CCF)F
InChI Key: IKYGJSBKPPIKJK-JDKVAZDPSA-N
Can. SMILES: CN1CCN(CC1)C2=C(C3=C(C=C2F)C(=O)C(=CN3CCF)C(=O)OCC4=C(C(=O)O)N5C(=O)[C@H]([C@H]5SC4)NC(=O)/C(=N\OC)/C6=CSC(=N6)N)F
InChI: InChI=1S/C31H31F3N8O8S2/c1-39-5-7-40(8-6-39)24-17(33)9-15-23(19(24)34)41(4-3-32)10-16(25(15)43)30(48)50-11-14-12-51-28-21(27(45)42(28)22(14)29(46)47)37-26(44)20(38-49-2)18-13-52-31(35)36-18/h9-10,13,21,28H,3-8,11-12H2,1-2H3,(H2,35,36)(H,37,44)(H,46,47)/b38-20-/t21-,28-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5486700#section=Literature
Citations:
  • http://jac.oxfordjournals.org/content/31/2/273.long
  • https://doi.org/10.1128/aac.33.7.1067

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