Basic information
- Standard SMILES
CN1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(CCF)c3c2F)CC1- InChIKey
XBJBPGROQZJDOJ-UHFFFAOYSA-N- Molecular formula
- C17H18F3N3O3
- Average molar mass
- 369.34 g/mol
- Monoisotopic mass
- 369.1300261
Overview
Fleroxacin is a fluoroquinolone antibiotic that is 4-oxo-1,4-dihydroquinoline which is substituted at positions 1, 3, 6, 7 and 8 by 2-fluoroethyl, carboxy, fluoro, 4-methylpiperazin-1-yl and fluoro groups, respectively. It is active against many Gram-positive and Gram-negative bacteria. It has a role as an antibacterial drug, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor and a topoisomerase IV inhibitor. It is a monocarboxylic acid, a member of quinolines, a difluorobenzene, a N-alkylpiperazine and a fluoroquinolone antibiotic.
Names & identifiers
- Preferred name
- Fleroxacin
- IUPAC
- 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
Names & synonyms
fleroxacin79660-72-3MegaloneMegalocinFleroxicinFleroxacinoQuinodisFleroxacineFleroxacinumAM-833AM 833FLRX
Show more names
6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acidRo 23-6240/000DTXSID1046714Ro-236240CHEBI:31810Ro-23-6240/000N804LDH51KRo-236240000
Database identifiers
- CAS
79660-72-3- PubChem CID
- 3357
- DTXSID
DTXSID1046714- ChEMBL
CHEMBL6273- ChEBI
CHEBI:31810- UNII
- N804LDH51K
- EC Number
- 677-525-2
- Nikkaji
- J23.768J
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 64.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 595
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use
Pharmaceuticals -> Listed in ZINC15
LogP0.04
Human DrugsPharmaceuticals
Dissociation Constants
8.8
5.5
5.5
8.2
Collision Cross Section189.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
Safety & regulation
GHS classification
GHS Classification
Warning
H371 (100%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]
P260, P264, P270, P308+P316, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSTOT SE 2 (100%)
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
PharmacodynamicsFleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It strongly inhibits the DNA-supercoiling activity of DNA gyrase.
Mechanism of ActionThe inhibition of DNA gyrase and DNA topoisomerase 2 leads ultimately to cell death as these enzymes are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
Absorption, Distribution and ExcretionRapidly and well absorbed from the gastrointestinal tract after oral administration.
Uses & manufacturing
Use ClassificationPharmaceuticals
Related reactions
3 records
Linked notes
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