fleroxacin

CHEBI:31810 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

fluoroquinolone antibioticARO:0000001

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25384 CHEBI:25384
CHEBI:26513 CHEBI:26513
CHEBI:38582 CHEBI:38582
CHEBI:46845 CHEBI:46845
CHEBI:87211 CHEBI:87211
ARO:0000001 ARO:0000001

Chemical structure

Computed structure properties
Molecular formula	C17H18F3N3O3
Charge	0
Average mass	369.343 Da
Monoisotopic mass	369.13003 Da
Source	ChEBI
InChIKey	XBJBPGROQZJDOJ-UHFFFAOYSA-N

SMILES

CN1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(CCF)c3c2F)CC1

InChI

InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)

Also called

6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (EXACT_SYNONYM)— chebi
6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid- (EXACT_SYNONYM)— chebi
fleroxacine (EXACT_SYNONYM)— chebi
fleroxacino (EXACT_SYNONYM)— chebi
fleroxacinum (EXACT_SYNONYM)— chebi
Megalocin (EXACT_SYNONYM)— aro
Quinodis (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004013
cas:79660-72-3
drugbank:DB04576
drugcentral:1177
kegg.compound:C13179
kegg.drug:D01716
lincs.smallmolecule:LSM-6633
patent:US4398029
reaxys:4300996
wikipedia.en:Fleroxacin
chembl:CHEMBL6273
pubchem.compound:3357

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3004013`	fleroxacin	`antibioticmech:aro-8f29f0a6d7`	2026-08-30
CHEBI	`CHEBI:31810`	fleroxacin	`antibioticmech:chebi-0aae8b0219`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

fluoroquinolone sensitive gyrA PROTEIN DIRECT_BINDING_TARGET

ARO:3000733

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO explicitly describes ligand binding to gyrase subunit A. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000733 (CARD/ARO asserts targeted_by_antibiotic ARO:3004013 (fleroxacin); database assertion, not a primary citation.)

fluoroquinolone sensitive gyrB PROTEIN DIRECT_BINDING_TARGET

ARO:3003261

CARD/ARO database assertion; target organism, strain, and assay are not specified. GyrB is asserted as the fluoroquinolone-sensitive subunit. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003261 (CARD/ARO asserts targeted_by_antibiotic ARO:3004013 (fleroxacin); database assertion, not a primary citation.)

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION microbial target — Assigned from ChEBI role CHEBI:50750 (EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor), CHEBI:53559 (topoisomerase IV inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.