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 microrganisms [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 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.

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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
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.

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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
No information available.
Summary of Clinical Use Click here for help
Gemifloxacin mesylate has approval from the US FDA with a 'Boxed Warning' to highlight the risk of serious adverse reactions. It is indicated for the treatment of infections caused by susceptible strains of bacteria, including acute bacterial exacerbation of chronic bronchitis and community-acquired pneumonia (CAP), only when no other treatment options are available. The drug was marketed in the US (under the trade name Factive®) but has since been discontinued. The European Medicines Agency (EMA) withdrew approval for Factive® in 2009 [1].
External links Click here for help
For extended ADME data see the following:

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