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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL31
CHEMBL31
Compound Name GATIFLOXACIN
ChEMBL Synonyms BMS-206584-01 | GATIFLOXACIN | TEQUIN | ZYMAXID | AM-1155 | ZYMAR
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names GATIFLOXACIN | TEQUIN | ZYMAXID | ZYMAR
Molecular Formula C19H22FN3O4

Additional synonyms for CHEMBL31 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1c(N2CCNC(C)C2)c(F)cc3C(=O)C(=CN(C4CC4)c13)C(=O)O
Standard InChI InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(1 ...
Download InChI
Standard InChI Key XUBOMFCQGDBHNK-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL31

Molecule Features

CHEMBL31 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:N Availability Type:Prescription-only

Withdrawal Information

Year 2006
Country United States
Reason Increased risk of dysglycemia
Class Gastrotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA gyrase inhibitor DNA gyrase FDA
Topoisomerase IV inhibitor Topoisomerase IV FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Conjunctivitis, BacterialD003234EFO:1000829bacterial conjunctivitis3ClinicalTrials
Communicable DiseasesD003141EFO:0005741infectious disease3ClinicalTrials
CataractD002386EFO:0001059cataract1ClinicalTrials
TuberculosisD014376Orphanet:3389Tuberculosis3ClinicalTrials
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials

Clinical Data

ClinicalTrials.gov GATIFLOXACIN
The Cochrane Collaboration GATIFLOXACIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL31. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4088 Topoisomerase IV subunit A Staphylococcus aureus 1.000
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.387

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
375.4 375.1594 1.98 4 83.8 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 2 0 7 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.43 8.71 2.1 -.15 2 27 0.85

Structural Alerts

There are 2 structural alerts for CHEMBL31. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01M - QUINOLONE ANTIBACTERIALS
J01MA - Fluoroquinolones
J01MA16 - gatifloxacin

S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AE - Fluoroquinolones
S01AE06 - gatifloxacin

ChemSpider ChemSpider:XUBOMFCQGDBHNK-UHFFFAOYSA-N
DailyMed gatifloxacin
PubChem SID: 103905240 SID: 104171401 SID: 124888832 SID: 144204535 SID: 170465592 SID: 26748958 SID: 861394
Wikipedia Gatifloxacin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL31



ACToR 112811-59-3 160738-57-8
BindingDB 50117914
ChEBI 5280
ChemicalBook CB2726045
DrugBank DB01044
DrugCentral 1280
eMolecules 31782258 901933
EPA CompTox Dashboard DTXSID5045704
Human Metabolome Database HMDB0015178
IBM Patent System BBCF444C470B633213796B6B385DC61C
KEGG Ligand C07661
LINCS LSM-5139
Mcule MCULE-4557972261
MolPort MolPort-001-738-626 MolPort-000-776-959
NIH Clinical Collection SAM002589955
Nikkaji J523.172H
PharmGKB PA449738
PubChem 5379 4872633
PubChem: Drugs of the Future 12014137
PubChem: Thomson Pharma 14755600
Selleck Gatifloxacin
SureChEMBL SCHEMBL22591

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/XUBOMFCQGDBHNK-UHFFFAOYSA-N spacer
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