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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1200393
CHEMBL1200393
Compound Name GREPAFLOXACIN HYDROCHLORIDE
ChEMBL Synonyms GREPAFLOXACIN HYDROCHLORIDE | RAXAR | OPC-17116
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names RAXAR
Molecular Formula C19H23ClFN3O3

Additional synonyms for CHEMBL1200393 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cl.CC1CN(CCN1)c2cc3N(C=C(C(=O)O)C(=O)c3c(C)c2F)C4CC4
Standard InChI InChI=1S/C19H22FN3O3.ClH/c1-10-8-22(6-5-21-10)15-7-14-16(11( ...
Download InChI
Standard InChI Key IEPMBYOIQGCVHO-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • USP Dictionary of USAN and International Drug Names
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL1200393

Molecule Features

CHEMBL1200393 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1999
Country United States; United Kingdom; United States; Germany
Reason Cardiac repolarization; QTc interval prolongation
Class Cardiotoxicity

Mechanism of Action

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

Clinical Data

ClinicalTrials.gov GREPAFLOXACIN HYDROCHLORIDE
The Cochrane Collaboration GREPAFLOXACIN HYDROCHLORIDE

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 CHEMBL1200393. 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.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1899 Serotonin 3a (5-HT3a) receptor Homo sapiens 0.871

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4088 Topoisomerase IV subunit A Staphylococcus aureus 1.000
CHEMBL1899 Serotonin 3a (5-HT3a) receptor Homo sapiens 0.742

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
359.4 359.1645 2.28 3 74.57 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 6 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.44 8.74 2.57 .62 2 26 0.88

Structural Alerts

There are 2 structural alerts for CHEMBL1200393. To view alerts please click here.

Compound Cross References

ChemSpider ChemSpider:IEPMBYOIQGCVHO-UHFFFAOYSA-N
PubChem SID: 144206077 SID: 170466148

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1200393



ACToR 161967-81-3
eMolecules 2729394
EPA CompTox Dashboard DTXSID0046692
PubChem 656829
PubChem: Drugs of the Future 12014640
PubChem: Thomson Pharma 15317353
SureChEMBL SCHEMBL137804

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