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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:29 UTC
HMDB IDHMDB0014363
Secondary Accession Numbers
  • HMDB14363
Metabolite Identification
Common NameMoxifloxacin
DescriptionMoxifloxacin is only found in individuals that have used or taken this drug. It is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox (in some countries also Avalox) for oral treatment.The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division.
Structure
Data?1582753169
Synonyms
ValueSource
1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-((4as,7as)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-3-quinolinecarboxylic acidChEBI
1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-((4as,7as)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-3-quinolinecarboxylateGenerator
BAY 12-8039HMDB
AvaloxHMDB
ActiraHMDB
IziloxHMDB
1-Cyclopropyl--7-(2,8-diazabicyclo(4.3.0)non-8-yl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHMDB
ProfloxHMDB
AveloxHMDB
OctegraHMDB
Moxifloxacin hydrochlorideHMDB
Chemical FormulaC21H24FN3O4
Average Molecular Weight401.4314
Monoisotopic Molecular Weight401.175084476
IUPAC Name7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Traditional Namemoxifloxacin
CAS Registry Number354812-41-2
SMILES
[H][C@]12CN(C[C@@]1([H])NCCC2)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1OC)C(O)=O
InChI Identifier
InChI=1S/C21H24FN3O4/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,16+/m0/s1
InChI KeyFABPRXSRWADJSP-MEDUHNTESA-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
  • Aminoquinoline
  • Haloquinoline
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyrrolopyridine
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Methoxyaniline
  • Anisole
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aryl halide
  • Aryl fluoride
  • Benzenoid
  • Piperidine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Tertiary amine
  • Amino acid
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organooxygen compound
  • Amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • 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 Point238 - 242 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.17 g/LNot Available
LogP2.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP10(0.01) g/LALOGPS
logP10(-0.5) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)5.69ChemAxon
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.11 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.22 m³·mol⁻¹ChemAxon
Polarizability41.24 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Moxifloxacin[H][C@]12CN(C[C@@]1([H])NCCC2)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1OC)C(O)=O4140.9Standard polar33892256
Moxifloxacin[H][C@]12CN(C[C@@]1([H])NCCC2)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1OC)C(O)=O3103.5Standard non polar33892256
Moxifloxacin[H][C@]12CN(C[C@@]1([H])NCCC2)C1=C(F)C=C2C(=O)C(=CN(C3CC3)C2=C1OC)C(O)=O3892.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Moxifloxacin,1TMS,isomer #1COC1=C(N2C[C@@H]3CCCN[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3488.8Semi standard non polar33892256
Moxifloxacin,1TMS,isomer #2COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O)C2=O3460.7Semi standard non polar33892256
Moxifloxacin,2TMS,isomer #1COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3370.3Semi standard non polar33892256
Moxifloxacin,2TMS,isomer #1COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O3363.2Standard non polar33892256
Moxifloxacin,2TMS,isomer #1COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C)C2=O4284.6Standard polar33892256
Moxifloxacin,1TBDMS,isomer #1COC1=C(N2C[C@@H]3CCCN[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3657.6Semi standard non polar33892256
Moxifloxacin,1TBDMS,isomer #2COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C(C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O)C2=O3712.7Semi standard non polar33892256
Moxifloxacin,2TBDMS,isomer #1COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C(C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3787.6Semi standard non polar33892256
Moxifloxacin,2TBDMS,isomer #1COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C(C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O3777.3Standard non polar33892256
Moxifloxacin,2TBDMS,isomer #1COC1=C(N2C[C@@H]3CCCN([Si](C)(C)C(C)(C)C)[C@@H]3C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O[Si](C)(C)C(C)(C)C)C2=O4391.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Moxifloxacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vk-2009000000-a015086b9091b8f0a01c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moxifloxacin GC-MS (1 TMS) - 70eV, Positivesplash10-0532-9002800000-074d91d14e42a22095e22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moxifloxacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moxifloxacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Moxifloxacin LC-ESI-qTof , Positive-QTOFsplash10-0udi-0391000000-7a74ddcc516a82243c1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moxifloxacin , positive-QTOFsplash10-0udi-0176900000-5ca9cd234a2a93f056582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moxifloxacin , positive-QTOFsplash10-0udi-0391000000-7a74ddcc516a82243c1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moxifloxacin 35V, Positive-QTOFsplash10-0f89-0019400000-cf921582bd429011cbc32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 10V, Positive-QTOFsplash10-0udi-1007900000-e058a02aff7730448f352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 20V, Positive-QTOFsplash10-0kal-7009100000-20887d53097f34d4f8db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 40V, Positive-QTOFsplash10-000x-9001000000-488b7c8794d94ce095f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 10V, Negative-QTOFsplash10-0pb9-0009400000-a8b883ca06c5e9c9fcf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 20V, Negative-QTOFsplash10-0adl-0009000000-d8b9065b2e67e4a5b7e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 40V, Negative-QTOFsplash10-01qc-1059000000-907a920eb60e4817917f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 10V, Negative-QTOFsplash10-0udi-0000900000-d6fe7783fba51472650a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 20V, Negative-QTOFsplash10-0udi-0004900000-3c89b98713ba31eddc162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 40V, Negative-QTOFsplash10-0a5a-0349000000-f4d9d1179ea22e8223232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 10V, Positive-QTOFsplash10-0udi-0000900000-837f69f2637af670669c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 20V, Positive-QTOFsplash10-001i-0009000000-bc46ed10c6db6c0006972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moxifloxacin 40V, Positive-QTOFsplash10-0002-5229000000-23e84289b8d0e4a64ce82021-09-24Wishart 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 DB00218 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00218 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00218
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID134802
KEGG Compound IDC07663
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMoxifloxacin
METLIN IDNot Available
PubChem Compound152946
PDB IDMFX
ChEBI ID63611
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. Ginsburg AS, Hooper N, Parrish N, Dooley KE, Dorman SE, Booth J, Diener-West M, Merz WG, Bishai WR, Sterling TR: Fluoroquinolone resistance in patients with newly diagnosed tuberculosis. Clin Infect Dis. 2003 Dec 1;37(11):1448-52. Epub 2003 Nov 4. [PubMed:14614666 ]

Enzymes

General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:
TOP2A
Uniprot ID:
P11388
Molecular weight:
174383.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Reuveni D, Halperin D, Shalit I, Priel E, Fabian I: Moxifloxacin enhances etoposide-induced cytotoxic, apoptotic and anti-topoisomerase II effects in a human colon carcinoma cell line. Int J Oncol. 2010 Aug;37(2):463-71. [PubMed:20596674 ]
  3. Wohlkonig A, Chan PF, Fosberry AP, Homes P, Huang J, Kranz M, Leydon VR, Miles TJ, Pearson ND, Perera RL, Shillings AJ, Gwynn MN, Bax BD: Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance. Nat Struct Mol Biol. 2010 Sep;17(9):1152-3. doi: 10.1038/nsmb.1892. Epub 2010 Aug 29. [PubMed:20802486 ]