Compound ID | 158

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Nemonoxacin

Synonym(s): TG-873870 (Taigexyn)

Class: Quinolone

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: DNA synthesis inhibitor. Inhibits bacterial DNA gyrase and topoisomerase IV, thereby inhibiting bacterial DNA replication.
Target Pathogen: Staphylococcus aureus (MSSA, MRSA and selected resistant phenotypes), Staphylococcus epidermidis, Streptococcus pneumoniae (including penicillin- and fluoroquinolone-resistant isolates), Enterococcus faecalis, Enterococcus faecium (including VRE), Escherichia coli, Klebsiella pneumoniae, Klebsiella oxytoca, Proteus mirabilis, Pseudomonas aeruginosa, Acinetobacter baumannii, Haemophilus influenzae, Neisseria gonorrhoeae, Helicobacter pylori, Chlamydia trachomatis and Chlamydia pneumoniae.
Combined with other compounds: Yes
Propensity to select resistant mutants: Low
Description: Synthetic, non-fluorinated quinolone antibacterial developed in oral and intravenous formulations; approved as nemonoxacin malate (Taigexyn®) in Taiwan and subsequently in China.
Institute where first reported: Procter & Gamble Pharmaceuticals
Year first mentioned: 2001
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 371.43
Iso. SMILES: C[C@H]1C[C@@H](CN(C1)C2=C(C3=C(C=C2)C(=O)C(=CN3C4CC4)C(=O)O)OC)N
InChI Key: AVPQPGFLVZTJOR-RYUDHWBXSA-N
Can. SMILES: C[C@H]1C[C@@H](CN(C1)C2=CC=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)N
InChI: InChI=1S/C20H25N3O4/c1-11-7-12(21)9-22(8-11)16-6-5-14-17(19(16)27-2)23(13-3-4-13)10-15(18(14)24)20(25)26/h5-6,10-13H,3-4,7-9,21H2,1-2H3,(H,25,26)/t11-,12-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/11993740
Guide to Pharmacology: nemonoxacin
Citations:
  • http://aac.asm.org/content/57/7/2942.full
  • http://aac.asm.org/content/58/10/6116.full
  • https://www.ncbi.nlm.nih.gov/pubmed/25079302
  • https://www.taiwan-healthcare.org/biotech/biotech-product?vendorSysid=BhsProducts20161115182506986696315
    • Patents:
  • US6329391B1
  • WO2007110834A2
  • WO2009023473A2
  • WO2010002415A1
  • WO2010002965A2
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