Nemonoxacin

Nemonoxacin
Names
	Preferred IUPAC name 7-[(3S,5S)-3-Amino-5-methylpiperidin-1-yl]-1-cyclopropyl-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Identifiers
CAS Number	378746-64-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:136053;
ChEMBL	ChEMBL1213456;
ChemSpider	10166207;
DrugBank	DB06600;
IUPHAR/BPS	10836;
PubChem CID	11993740;
UNII	P94L0PVO94;
CompTox Dashboard (EPA)	DTXSID10958907 ;
	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 Key: AVPQPGFLVZTJOR-RYUDHWBXSA-N; InChI=1/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 Key: AVPQPGFLVZTJOR-RYUDHWBXBZ;
	SMILES C[C@H]1C[C@H](N)CN(C1)c2ccc3c(c2OC)n(C4CC4)cc(c3=O)C(=O)O;
Properties
Chemical formula	C20H25N3O4
Molar mass	371.437 g·mol−1
Pharmacology
ATC code	J01MB08 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nemonoxacin is a non-fluorinated quinolone antibiotic undergoing clinical trials.^[1] It has the same mechanism of action as fluouroquinolones; it inhibits DNA gyrase, preventing DNA synthesis, gene duplication, and cell division. At the end of 2016, it had reached market in Taiwan, Russia, the Commonwealth Independent States, Turkey, mainland China,^[2] and Latin America^[3] under the brand name Taigexyn. Nemonoxacin has completed phase 2 trials in the US and has moved on to phase 3 trials.^[4] The U.S. Food and Drug Administration (FDA) has granted nemonoxacin qualified infectious disease product (QIDP) and fast track designations for community-acquired bacterial pneumonia (CAP) and acute bacterial skin and skin-structure infections (ABSSSI).^[5]

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Nemonoxacin has a broad spectrum of activity against Gram-positive, Gram-negative, and atypical pathogens, including activity against methicillin-resistant Staphylococcus aureus (MRSA) (MIC90 1 μg/ml) and vancomycin-resistant pathogens.^[6]^[7] However, it was less active against Gram-negative pathogens such as Escherichia coli, Proteus mirabilis, and Pseudomonas aeruginosa, with MIC90 values of 32, 16, and 32 μg/ml, respectively.^[8] The new drug also is effective against C.difficile isolates that are resistant to other quinolones,^[9] and is more potent than levofloxacin or moxifloxacin.^[10]

References