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Gemifloxacin

July 24, 2017
Common Name

Gemifloxacin Description

Gemifloxacin is an oral broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. Gemifloxacin acts by inhibiting DNA synthesis through the inhibition of both DNA gyrase and topoisomerase IV, which are essential for bacterial growth. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source FactivKegg Gemifloxacin mesilateHMDB Gemifloxacin mesylateHMDB 7-(3-Aminomethyl-4-methoxyimino-pyrrolidine-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-(1,8)-naphthyridine-3-carboxylic acidMeSH FactiveMeSH

Chemical Formlia

C18H20FN5O4 Average Molecliar Weight

389.3809 Monoisotopic Molecliar Weight

389.149932358 IUPAC Name

7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Traditional Name

gemifloxacin CAS Registry Number

175463-14-6 SMILES

CON=C1/CN(CC1CN)C1=NC2=C(C=C1F)C(=O)C(=CN2C1CC1)C(O)=O

InChI Identifier

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 Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. These are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Diazanaphthalenes Sub Class

Naphthyridines Direct Parent

Naphthyridine carboxylic acids and derivatives Alternative Parents

  • Fluoroquinolones
  • Pyridinecarboxylic acids
  • Dialkylarylamines
  • Aminopyridines and derivatives
  • Aryl fluorides
  • Imidolactams
  • Vinylogous amides
  • Pyrrolidines
  • Heteroaromatic compounds
  • Oxime ethers
  • Amino acids
  • Azacyclic compounds
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Hydrocarbon derivatives
  • Monoalkylamines
  • Organic oxides
  • Organofluorides
  • Organooxygen compounds
  • Organopnictogen compounds

    • Substituents

  • Naphthyridine carboxylic acid
  • Fluoroquinolone
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Dialkylarylamine
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Aryl fluoride
  • Aryl halide
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrolidine
  • Amino acid
  • Amino acid or derivatives
  • Oxime ether
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organohalogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • monocarboxylic acid (CHEBI:101853 )
  • 1,8-naphthyridine derivative (CHEBI:101853 )
  • quinolone antibiotic (CHEBI:101853 )
  • fluoroquinolone antibiotic (CHEBI:101853 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Quinolones

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility2.10e-01 g/LNot Available LogP2.3Not Available

    Predicted Properties

    Property Value Source Water Solubility0.21 mg/mLALOGPS logP-0.82ALOGPS logP-0.92ChemAxon logS-3.3ALOGPS pKa (Strongest Acidic)5.53ChemAxon pKa (Strongest Basic)9.53ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count9ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area121.35 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity99.74 m3·mol-1ChemAxon Polarizability39.3 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01155

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01155

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01155 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    7845573 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Gemifloxacin NuGOwiki Link

    HMDB15286 Metagene Link

    HMDB15286 METLIN ID

    Not Available PubChem Compound

    9571107 PDB ID

    Not Available ChEBI ID

    101853

    Product: DAB

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 22485150

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