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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:19 UTC
HMDB IDHMDB0015286
Secondary Accession Numbers
  • HMDB15286
Metabolite Identification
Common NameGemifloxacin
DescriptionGemifloxacin, also known as factiv, belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group. Gemifloxacin is a drug which is used for the treatment of bacterial infection caused by susceptible strains such as s. pneumoniae, h. influenzae, h. parainfluenzae, or m. catarrhalis, s. pneumoniae (including multi-drug resistant strains [mdrsp]), m. pneumoniae, c. pneumoniae, or k. pneumoniae. Gemifloxacin is a very strong basic compound (based on its pKa). All metabolites formed are minor (<10% of the administered oral dose); the principal ones are N-acetyl gemifloxacin, the E-isomer of gemifloxacin and the carbamyl glucuronide of gemifloxacin. It is available in oral formulations. The bactericidal action of gemifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination. Gemifloxacin is a quinolone/fluoroquinolone antibiotic. Gemifloxacin is metabolized to a limited extent by the liver. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gemifloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two.
Structure
Data?1582753279
Synonyms
ValueSource
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 acidHMDB
FactiveHMDB
Chemical FormulaC18H20FN5O4
Average Molecular Weight389.3809
Monoisotopic Molecular Weight389.149932358
IUPAC Name7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Namegemifloxacin
CAS Registry Number175463-14-6
SMILES
CO\N=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 KeyZRCVYEYHRGVLOC-HYARGMPZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassNaphthyridines
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.21 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.74 m³·mol⁻¹ChemAxon
Polarizability39.3 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-7009000000-6c1e062d9b76f111f18cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-5202900000-fac5d6018c989a382d60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0009000000-216eb233a8cd0c046a00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0096-0109000000-01212fa7e1d9f9ed8c9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qi-9301000000-91707fbf708434bd2935Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0009000000-1a9cdceacdbdcde5efa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-0019000000-998e1aa5045a6e80b457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ik9-0229000000-77756438384a40006769Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01155 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01155 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01155
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7845573
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGemifloxacin
METLIN IDNot Available
PubChem Compound9571107
PDB IDNot Available
ChEBI ID101853
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available