gemifloxacin

CHEBI:101853 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A 1,4-dihydro-1,8-naphthyridine with a carboxy group at the 3-position, an oxo sustituent at the 4-position, a fluoro substituent at the 5-position and a substituted pyrrolin-1-yl group at the 7-position. — 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:73537 CHEBI:73537
CHEBI:86324 CHEBI:86324
CHEBI:87211 CHEBI:87211
ARO:0000001 ARO:0000001

Chemical structure

Computed structure properties
Molecular formula	C18H20FN5O4
Charge	0
Average mass	389.387 Da
Monoisotopic mass	389.14993 Da
Source	ChEBI
InChIKey	ZRCVYEYHRGVLOC-HYARGMPZSA-N

SMILES

CO/N=C1\CN(c2nc3c(cc2F)c(=O)c(C(=O)O)cn3C2CC2)CC1CN

InChI

InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+

Also called

7-[3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (EXACT_SYNONYM)— chebi
Factive (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3007165
beilstein:8361408
cas:175463-14-6
drugbank:DB01155
drugcentral:1286
kegg.drug:D08012
patent:EP688772
patent:US5633262
wikipedia.en:Gemifloxacin
chembl:CHEMBL430
pubchem.compound:9571107

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:3007165`	gemifloxacin	`antibioticmech:aro-c73254b42a`	2026-08-30
CHEBI	`CHEBI:101853`	gemifloxacin	`antibioticmech:chebi-21227c4a6b`	2026-08-30

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION microbial target — Assigned from ChEBI role 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.

Resistance mechanisms

1 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Clostridioides difficile gyrB conferring resistance to fluoroquinolones	ARO:3004562	not organism-specific	—	ARO:3004562 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007165 (gemifloxacin); database assertion, not a primary citation.)

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

Provenance

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