U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula 2C20H25N3O4.2C4H6O5.H2O
Molecular Weight 1029.0506
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEMONOXACIN MALATE HEMIHYDRATE

SMILES

O.OC(CC(O)=O)C(O)=O.OC(CC(O)=O)C(O)=O.COC1=C2N(C=C(C(O)=O)C(=O)C2=CC=C1N3C[C@@H](C)C[C@H](N)C3)C4CC4.COC5=C6N(C=C(C(O)=O)C(=O)C6=CC=C5N7C[C@@H](C)C[C@H](N)C7)C8CC8

InChI

InChIKey=XNVZOGKOFKLWFQ-ABLBMNRKSA-N
InChI=1S/2C20H25N3O4.2C4H6O5.H2O/c2*1-11-7-12(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;2*5-2(4(8)9)1-3(6)7;/h2*5-6,10-13H,3-4,7-9,21H2,1-2H3,(H,25,26);2*2,5H,1H2,(H,6,7)(H,8,9);1H2/t2*11-,12-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H25N3O4
Molecular Weight 371.4302
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Nemonoxacin is a non-fluorinated quinolone antibiotic in clinical development in an oral and intravenous formulation. It exhibits potent antibacterial activities against Gram-positive, Gram-negative, and atypical pathogens, especially methicillin-resistant Staphylococcus aureus. The molecule inhibits bacterial DNA synthesis by forming a ternary complex with a DNA molecule and gyrase and topoisomerase IV enzymes, thus blocking bacterial DNA supercoiling. Nemonoxacin is developed by TaiGen Biotechnology Company and has reached worldwide approval in 2014 and is marketed under the name Taigexyn®.

Approval Year

PubMed

PubMed

TitleDatePubMed
New antibiotics for antibiotic-resistant bacteria.
2009 May 28
Gateways to clinical trials.
2010 Jun
In vivo antibacterial activity of nemonoxacin, a novel non-fluorinated quinolone.
2010 Nov
In vitro activity of nemonoxacin, tigecycline, and other antimicrobial agents against Helicobacter pylori isolates in Taiwan, 1998-2007.
2010 Nov
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 03:08:14 GMT 2023
Edited
by admin
on Sat Dec 16 03:08:14 GMT 2023
Record UNII
Y97F3051FH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEMONOXACIN MALATE HEMIHYDRATE
Common Name English
TAIGEXYN
Brand Name English
BUTANEDIOIC ACID, 2-HYDROXY-, COMPD. WITH 7-((3S,5S)-3-AMINO-5-METHYL-1-PIPERIDINYL)-1-CYCLOPROPYL-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID, HYDRATE (2:2:1)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID10241765
Created by admin on Sat Dec 16 03:08:14 GMT 2023 , Edited by admin on Sat Dec 16 03:08:14 GMT 2023
PRIMARY
CAS
951313-26-1
Created by admin on Sat Dec 16 03:08:14 GMT 2023 , Edited by admin on Sat Dec 16 03:08:14 GMT 2023
PRIMARY
FDA UNII
Y97F3051FH
Created by admin on Sat Dec 16 03:08:14 GMT 2023 , Edited by admin on Sat Dec 16 03:08:14 GMT 2023
PRIMARY
PUBCHEM
71587894
Created by admin on Sat Dec 16 03:08:14 GMT 2023 , Edited by admin on Sat Dec 16 03:08:14 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY