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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:07 UTC
HMDB IDHMDB0015178
Secondary Accession Numbers
  • HMDB15178
Metabolite Identification
Common NameGatifloxacin
DescriptionGatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial enzymes DNA gyrase and topoisomerase IV. Bristol-Myers Squibb introduced Gatifloxacin in 1999 under the proprietary name Tequin for the treatment of respiratory tract infections, having licensed the medication from Kyorin Pharmaceutical Company of Japan. Allergan produces an eye-drop formulation called Zymar. Gatifloxacin is available as tablets and in various aqueous solutions for intravenous therapy. [Wikipedia ]
Structure
Data?1582753267
Synonyms
ValueSource
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acidChEBI
1-Cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acidChEBI
AM 1155ChEBI
GatifloxacineChEBI
GatifloxacinoChEBI
GatifloxacinumChEBI
Gatifloxacin anhydrousKegg
ZymerKegg
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylateGenerator
1-Cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylateGenerator
TequinMeSH
ZymarMeSH
Chemical FormulaC19H22FN3O4
Average Molecular Weight375.3941
Monoisotopic Molecular Weight375.159434412
IUPAC Name1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional Namegatifloxacin
CAS Registry Number112811-59-3
SMILES
COC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC1
InChI Identifier
InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)
InChI KeyXUBOMFCQGDBHNK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-3-carboxylic acid
  • Fluoroquinolone
  • N-arylpiperazine
  • Aminoquinoline
  • Haloquinoline
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Methoxyaniline
  • Anisole
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Piperazine
  • Benzenoid
  • 1,4-diazinane
  • Aryl halide
  • Pyridine
  • Aryl fluoride
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary amine
  • Amino acid or derivatives
  • Amino acid
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Ether
  • Secondary aliphatic amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.63 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available189.47http://allccs.zhulab.cn/database/detail?ID=AllCCS00001031
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP10(-0.23) g/LALOGPS
logP10(-0.58) g/LChemAxon
logS10(-2.8) g/LALOGPS
pKa (Strongest Acidic)5.69ChemAxon
pKa (Strongest Basic)8.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.11 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.82 m³·mol⁻¹ChemAxon
Polarizability38.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+182.49130932474
DeepCCS[M-H]-180.13430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GatifloxacinCOC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC13647.1Standard polar33892256
GatifloxacinCOC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC12875.2Standard non polar33892256
GatifloxacinCOC1=C2N(C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1)C1CC13523.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gatifloxacin,1TMS,isomer #1COC1=C(N2CCNC(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3325.2Semi standard non polar33892256
Gatifloxacin,1TMS,isomer #2COC1=C(N2CCN([Si](C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O)C2=O3347.1Semi standard non polar33892256
Gatifloxacin,2TMS,isomer #1COC1=C(N2CCN([Si](C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3282.9Semi standard non polar33892256
Gatifloxacin,2TMS,isomer #1COC1=C(N2CCN([Si](C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3119.6Standard non polar33892256
Gatifloxacin,2TMS,isomer #1COC1=C(N2CCN([Si](C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3760.2Standard polar33892256
Gatifloxacin,1TBDMS,isomer #1COC1=C(N2CCNC(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3478.8Semi standard non polar33892256
Gatifloxacin,1TBDMS,isomer #2COC1=C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O)C2=O3571.5Semi standard non polar33892256
Gatifloxacin,2TBDMS,isomer #1COC1=C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3643.7Semi standard non polar33892256
Gatifloxacin,2TBDMS,isomer #1COC1=C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3513.3Standard non polar33892256
Gatifloxacin,2TBDMS,isomer #1COC1=C(N2CCN([Si](C)(C)C(C)(C)C)C(C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3921.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1009000000-78a39452af06b1f66c1d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (1 TMS) - 70eV, Positivesplash10-001i-2003900000-7300cb8bf451e3a14f812017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gatifloxacin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin DI-ESI-qTof , Negative-QTOFsplash10-0159-0019000000-9d9810e16459120201fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin LC-ESI-qTof , Positive-QTOFsplash10-00kr-0942000000-432aa78e495cb764bf6a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin LC-ESI-qTof , Positive-QTOFsplash10-000i-0922000000-8e80b2969083df9af7332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin , positive-QTOFsplash10-004i-0169000000-7839341ea49cae9ec8cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin , positive-QTOFsplash10-000i-0922000000-8e80b2969083df9af7332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin , positive-QTOFsplash10-004i-0279000000-0ee0061b508877e5251c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gatifloxacin , positive-QTOFsplash10-00kr-0942000000-432aa78e495cb764bf6a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 10V, Positive-QTOFsplash10-004i-0009000000-febde21288cfd8b65bba2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 20V, Positive-QTOFsplash10-000x-5009000000-2bb94673281db9c712502016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 40V, Positive-QTOFsplash10-0006-9012000000-ebdcd48decdc15ee504a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 10V, Negative-QTOFsplash10-0089-0009000000-97fc4892888449eada822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 20V, Negative-QTOFsplash10-0gwb-0039000000-0c4c3d30828e5db88fd62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 40V, Negative-QTOFsplash10-0a59-9053000000-4d294aabf5e9cb6ea3b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 10V, Positive-QTOFsplash10-056r-0009000000-cba07e04dae1eba32c792021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 20V, Positive-QTOFsplash10-0a4i-0009000000-3085d1f976b6e0a525382021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 40V, Positive-QTOFsplash10-05tf-3159000000-79cc5ce3bdd0230c28382021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 10V, Negative-QTOFsplash10-00e9-0009000000-8f66bae3e284a8e7f0182021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 20V, Negative-QTOFsplash10-03di-0029000000-750db431dd4870d399aa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gatifloxacin 40V, Negative-QTOFsplash10-00ri-0197000000-0b9db2d8ea5a518c1b832021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 DB01044 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01044 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5186
KEGG Compound IDC07661
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGatifloxacin
METLIN IDNot Available
PubChem Compound5379
PDB IDNot Available
ChEBI ID5280
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Park-Wyllie LY, Juurlink DN, Kopp A, Shah BR, Stukel TA, Stumpo C, Dresser L, Low DE, Mamdani MM: Outpatient gatifloxacin therapy and dysglycemia in older adults. N Engl J Med. 2006 Mar 30;354(13):1352-61. Epub 2006 Mar 1. [PubMed:16510739 ]
  2. Gurwitz JH: Serious adverse drug effects--seeing the trees through the forest. N Engl J Med. 2006 Mar 30;354(13):1413-5. Epub 2006 Mar 1. [PubMed:16510740 ]