amifloxacin   Click here for help

GtoPdb Ligand ID: 10758

Synonyms: compound 7 [PMID: 2834557] | WIN 49, 375 | WIN 49,375-3 | WIN-49375 | WIN49375
Compound class: Synthetic organic
Comment: Amifloxacin (WIN 49375) is a fluoroquinolone type II DNA topoisomerase (DNA gyrase) inhibitor antibacterial [1-2].

amifloxacin is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 77.81
Molecular weight 334.14
XLogP 2.2
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CNn1cc(C(=O)O)c(=O)c2c1cc(N1CCN(CC1)C)c(c2)F
Isomeric SMILES CNn1cc(C(=O)O)c(=O)c2c1cc(N1CCN(CC1)C)c(c2)F
InChI InChI=1S/C16H19FN4O3/c1-18-21-9-11(16(23)24)15(22)10-7-12(17)14(8-13(10)21)20-5-3-19(2)4-6-20/h7-9,18H,3-6H2,1-2H3,(H,23,24)
InChI Key RUXPNBWPIRDVTH-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-fluoro-1-(methylamino)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5557 amifloxacin
Synonyms Click here for help
compound 7 [PMID: 2834557] | WIN 49, 375 | WIN 49,375-3 | WIN-49375 | WIN49375
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Amifloxacin
Other databases
CAS Registry No. 86393-37-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL6231
GtoPdb PubChem SID 405560199
PubChem CID 55492
Search Google for chemical match using the InChIKey RUXPNBWPIRDVTH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone RUXPNBWPIRDVTH
Search PubMed clinical trials amifloxacin
Search PubMed titles amifloxacin
Search PubMed titles/abstracts amifloxacin
UniChem Compound Search for chemical match using the InChIKey RUXPNBWPIRDVTH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RUXPNBWPIRDVTH-UHFFFAOYSA-N

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MedChemExpress
Amifloxacin (links to external site)
Cat. No. HY-U00221