Compound ID | 453

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NB2030

Class: Beta-lactam; triclosan

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Fatty acid synthesis inhibitor. Able to outcompete penicillin G in binding to PBP of methicillin-resistant Staphylococcus aureus
Description: Cephalosporin linked to triclosan; act primarily as a enoyl reductase inhibitor
Institute where first reported: New Biotics (Kiadis Pharmaceuticals, Netherlands)
Year first mentioned: 2003
Development status: Experimental
Reason dropped: In vivo activity reduced due to high serum protein binding
Chemical structure(s):
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Molecular weight: 627.89
Iso. SMILES: O=C(N[C@]1([H])C(N2C1SCC(COC3=CC(C)=CC=C3OC4=CC=C(Cl)C=C4Cl)=C2C(O)=O)=O)CN5N=NN=C5.Cl
InChI Key: QSBRBFXYCZGDNT-VAQOXHRHSA-N
Can. SMILES: CC1=CC=C(C(=C1)OCC2=C(C(=O)O)N3C(=O)[C@]([H])(C3SC2)NC(=O)CN4C=NN=N4)OC5=CC=C(C=C5Cl)Cl.Cl
InChI: InChI=1S/C24H20Cl2N6O6S.ClH/c1-12-2-4-17(38-16-5-3-14(25)7-15(16)26)18(6-12)37-9-13-10-39-23-20(22(34)32(23)21(13)24(35)36)28-19(33)8-31-11-27-29-30-31;/h2-7,11,20,23H,8-10H2,1H3,(H,28,33)(H,35,36);1H/t20-,23?;/m1./s1
External links:
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC321519/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC321519/

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