gemifloxacin   Click here for help

GtoPdb Ligand ID: 12406

Synonyms: Factive® | LB20304 | SB 265805
Approved drug
gemifloxacin is an approved drug (FDA (2003))
Compound class: Synthetic organic
Comment: Gemifloxacin is a fluoroquinolone antibacterial compound with potent activity against both Gram-negative and Gram-positive microorganisms [2-3].
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 7
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 120.82
Molecular weight 389.38
XLogP 0.9
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 CO/N=C/1\CN(CC1CN)C2=NC3=C(C=C2F)C(=O)C(=CN3C4CC4)C(=O)O
Isomeric SMILES CO/N=C/1\CN(CC1CN)C2=C(C=C3C(=O)C(=CN(C3=N2)C4CC4)C(=O)O)F
InChI InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+
InChI Key ZRCVYEYHRGVLOC-HYARGMPZSA-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/)
References
1. European Medicines Agency. 
Withdrawal Assessment Report for Factive.
Accessed on 19/03/2023. Modified on 19/03/2023. https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-factive_en.pdf
2. Hong CY, Kim YK, Chang JH, Kim SH, Choi H, Nam DH, Kim YZ, Kwak JH. (1997)
Novel fluoroquinolone antibacterial agents containing oxime-substituted (aminomethyl)pyrrolidines: synthesis and antibacterial activity of 7-(4-(aminomethyl)-3-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6- fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid (LB20304).
J Med Chem, 40 (22): 3584-93. [PMID:9357525]
3. Oh JI, Paek KS, Ahn MJ, Kim MY, Hong CY, Kim IC, Kwak JH. (1996)
In vitro and in vivo evaluations of LB20304, a new fluoronaphthyridone.
Antimicrob Agents Chemother, 40 (6): 1564-8. [PMID:8726042]