ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL583
CHEMBL583
Compound Name GREPAFLOXACIN
ChEMBL Synonyms Raxar | GREPAFLOXACIN HYDROCHLORIDE | GREPAFLOXACIN | RAXAR | OPC-17116
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names RAXAR
Molecular Formula C19H22FN3O3

Additional synonyms for CHEMBL583 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC1CN(CCN1)c2cc3N(C=C(C(=O)O)C(=O)c3c(C)c2F)C4CC4
Standard InChI InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17 ...
Download InChI
Standard InChI Key AIJTTZAVMXIJGM-UHFFFAOYSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL583

Molecule Features

CHEMBL583 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Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials

Clinical Data

ClinicalTrials.gov GREPAFLOXACIN
The Cochrane Collaboration GREPAFLOXACIN

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 CHEMBL583. 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 CHEMBL583. 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
J01MA11 - grepafloxacin

ChemSpider ChemSpider:AIJTTZAVMXIJGM-UHFFFAOYSA-N
PubChem SID: 50112780
Wikipedia Grepafloxacin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL583



ACToR 119914-60-2
BindingDB 50117924
Brenda 13425
ChEBI 5543
DrugBank DB00365
DrugCentral 1330
EPA CompTox Dashboard DTXSID2048321
Human Metabolome Database HMDB0014509
IBM Patent System C84A07ACE6753982CB4B6E83037730BE
KEGG Ligand C11368
Nikkaji J384.494C
PharmGKB PA449812
PubChem 72474
PubChem: Thomson Pharma 14852426
SureChEMBL SCHEMBL34155

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