nemonoxacin   Click here for help

GtoPdb Ligand ID: 10836

Synonyms: Taigexyn® | TG-873870 | TG873870
Approved drug
nemonoxacin is an approved drug (Taiwan (2014))
Compound class: Synthetic organic
Comment: Nemonoxacin is a non-fluorinated quinolone antibacterial with broad-spectrum activity against Gram-positive and Gram-negative bacteria and atypical pathogens, including methicillin-resistant S. aureus (MRSA) and vancomycin-resistant pathogens [1-2]. It selectively inhibits bacterial DNA topoisomerase (DNA gyrase) activity.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 97.79
Molecular weight 371.18
XLogP 4.25
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES COc1c(ccc2c1n(cc(c2=O)C(=O)O)C1CC1)N1C[C@@H](C)C[C@@H](C1)N
Isomeric SMILES COc1c(ccc2c1n(cc(c2=O)C(=O)O)C1CC1)N1C[C@@H](C)C[C@@H](C1)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
InChI Key AVPQPGFLVZTJOR-RYUDHWBXSA-N
References
1. Chen YH, Liu CY, Lu JJ, King CH, Hsueh PR. (2009)
In vitro activity of nemonoxacin (TG-873870), a novel non-fluorinated quinolone, against clinical isolates of Staphylococcus aureus, enterococci and Streptococcus pneumoniae with various resistance phenotypes in Taiwan.
J Antimicrob Chemother, 64 (6): 1226-9. [PMID:19833635]
2. Chotikanatis K, Kohlhoff SA, Hammerschlag MR. (2014)
In vitro activity of nemonoxacin, a novel nonfluorinated quinolone antibiotic, against Chlamydia trachomatis and Chlamydia pneumoniae.
Antimicrob Agents Chemother, 58 (3): 1800-1. [PMID:24366753]
3. Lauderdale TL, Shiau YR, Lai JF, Chen HC, King CH. (2010)
Comparative in vitro activities of nemonoxacin (TG-873870), a novel nonfluorinated quinolone, and other quinolones against clinical isolates.
Antimicrob Agents Chemother, 54 (3): 1338-42. [PMID:20065058]
4. Poole RM. (2014)
Nemonoxacin: first global approval.
Drugs, 74 (12): 1445-53. [PMID:25079302]