Grepafloxacin
A fluoroquinolone antibiotic that was developed to treat respiratory and urinary tract infections but was voluntarily withdrawn from the market in 1999 due to concerns about serious cardiac arrhythmias, specifically QT interval prolongation. It worked by inhibiting bacterial DNA gyrase and topoisomerase IV. Its withdrawal contributed to greater scrutiny of cardiac safety in antibiotic development.
Molecular Weight
359.4000 g/mol
LogP
-0.20
TPSA
72.90 Ų
Lipinski RO5
Pass
Mechanism of Action
Inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV, enzymes essential for DNA replication, transcription, and repair. This leads to breakage of bacterial chromosomal DNA and rapid cell death.
Pharmacokinetics (PK)
Pharmacodynamics (PD)
Inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV, enzymes essential for DNA replication, transcription, and repair. This leads to breakage of bacterial chromosomal DNA and rapid cell death.
2D Structure
Cite this structure
Embed this structure
SMILES
Cc1c(F)c(N2CCNC(C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1
InChI
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
Molecular Formula
C19H22FN3O3
HBD / HBA
2 / 7
Rotatable Bonds
3
Heavy Atoms
26
No targets recorded
Target interaction data is not yet available for this drug.
No interactions recorded
Drug interaction data is not yet available for this compound.
No side effects recorded
Side effect data is not yet available for this drug.
Frequently Asked Questions
A fluoroquinolone antibiotic that was developed to treat respiratory and urinary tract infections but was voluntarily withdrawn from the market in 1999 due to concerns about serious cardiac arrhythmias, specifically QT interval prolongation. It worked by inhibiting bacterial DNA gyrase and topoisomerase IV. Its withdrawal contributed to greater scrutiny of cardiac safety in antibiotic development.
Inhibits bacterial DNA gyrase (topoisomerase II) and topoisomerase IV, enzymes essential for DNA replication, transcription, and repair. This leads to breakage of bacterial chromosomal DNA and rapid cell death.
Yes, Grepafloxacin is an approved drug. It has reached clinical phase 4. It is classified as a Small molecule.
References & Data Sources
- ChEMBL — European Bioinformatics Institute (EBI). CHEMBL583. Open-access bioactivity database.
- PubChem — National Center for Biotechnology Information (NCBI). CID 72474. Chemical information database.
Data aggregated from publicly available pharmacological databases. Last updated 2026-03-04.
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