gatifloxacin

CHEBI:5280 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A monocarboxylic acid that is 4-oxo-1,4-dihydroquinoline-3-carboxylic acid which is substituted on the nitrogen by a cyclopropyl group and at positions 6, 7, and 8 by fluoro, 3-methylpiperazin-1-yl, and methoxy groups, respectively. Gatifloxacin is an antibiotic of the fourth-generation fluoroquinolone family, that like other members of that family, inhibits the bacterial topoisomerase type-II enzymes. — 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.

Label unavailable CHEBI:23765
Label unavailable CHEBI:26512
Label unavailable CHEBI:37143
Label unavailable CHEBI:46848
quinolone antibiotic CHEBI:86324
fluoroquinolone antibiotic ARO:0000001

Chemical structure

Computed structure properties
Molecular formula	C19H22FN3O4
Charge	0
Average mass	375.4 Da
Monoisotopic mass	375.15943 Da
Source	ChEBI
InChIKey	XUBOMFCQGDBHNK-UHFFFAOYSA-N

SMILES

COc1c(N2CCNC(C)C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12

InChI

InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)

Also called

gatifloxacine (INN)— chebi
gatifloxacino (INN)— chebi
gatifloxacinum (INN)— chebi
1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (EXACT_SYNONYM)— chebi
1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (EXACT_SYNONYM)— chebi
1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acid (EXACT_SYNONYM)— chebi
AM 1155 (EXACT_SYNONYM)— chebi
AM-1155 (EXACT_SYNONYM)— aro
Tequin (EXACT_SYNONYM)— aro

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antimicrobial agent CHEBI:33281

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:3000659`	gatifloxacin	`antibioticmech:aro-297b0e164e`	2026-08-30
CHEBI	`CHEBI:5280`	gatifloxacin	`antibioticmech:chebi-d4276783f1`	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:3000659 (gatifloxacin); database assertion, not a primary citation.)

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:50750 (EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

10 observations · Browse all observations · Complete record (JSON.gz)

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	3 source isolates 3 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; KMVALIDATION2025; not specified	—	3 source isolates 3 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; KMVALIDATION2025; not specified	—	44 source isolates 44 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; solid media; middlebrook; 7H10; critical concentration 2.0 mg/L	—	9 source isolates 9 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; solid media; middlebrook; 7H10; critical concentration 2.0 mg/L	—	126 source isolates 126 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration 2.0 mg/L	—	3 source isolates 3 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration 2.0 mg/L	—	34 source isolates 34 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	69 source isolates 69 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

22 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 21

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii gyrA conferring resistance to fluoroquinolones	ARO:3003817	not organism-specific	—	ARO:3003817 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Acinetobacter baumannii parC conferring resistance to fluoroquinolones	ARO:3003818	not organism-specific	—	ARO:3003818 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Bartonella bacilliformis gyrA conferring resistance to fluoroquinolones	ARO:3003297	not organism-specific	—	ARO:3003297 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Clostridioides difficile gyrA conferring resistance to fluoroquinolones	ARO:3003995	not organism-specific	—	ARO:3003995 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Escherichia coli gyrA conferring resistance to fluoroquinolones	ARO:3003294	not organism-specific	—	ARO:3003294 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Escherichia coli parC conferring resistance to fluoroquinolones	ARO:3003308	not organism-specific	—	ARO:3003308 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Escherichia coli parE conferring resistance to fluoroquinolones	ARO:3003316	not organism-specific	—	ARO:3003316 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Morganella morganii gyrB conferring resistance to fluoroquinolones	ARO:3003306	not organism-specific	—	ARO:3003306 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Mycobacterium leprae gyrA conferring resistance to fluoroquinolones	ARO:3003298	not organism-specific	—	ARO:3003298 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Mycobacterium leprae gyrB conferring resistance to fluoroquinolones	ARO:3003304	not organism-specific	—	ARO:3003304 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Mycobacterium tuberculosis gyrA conferring resistance to fluoroquinolones	ARO:3003295	not organism-specific	—	ARO:3003295 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Mycobacterium tuberculosis gyrB with mutation conferring resistance to fluoroquinolones	ARO:3003459	not organism-specific	—	ARO:3003459 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Mycoplasma hominis parC conferring resistance to fluoroquinolones	ARO:3003310	not organism-specific	—	ARO:3003310 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Salmonella serovars gyrB conferring resistance to fluoroquinolones	ARO:3003307	not organism-specific	—	ARO:3003307 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Salmonella serovars parE conferring resistance to fluoroquinolones Evidence-scope review 2026-10-16-salmonella-pare-evidence-scope: The cited Enteritidis study found no independent parE effect in its tested background; an indirect contribution remained unresolved. This is not a universal inactivity claim or evidence for every serovar and inherited compound. Retain CARD's assertion as database evidence, without assigning an experimental protein, allele, taxon or susceptibility observation. Qualification references, not an upgrade of the CARD assertion: DOI:10.1128/aac.01005-08 (Results: Contribution of target gene mutations to quinolone resistance; Table 1: quinolone headers and relevant parE comparison; Table 3: compound headers and absence of a parE-specific comparison; Discussion: paragraph beginning Although complementation; publisher HTML text and selected table text; no visual table, figure or supplement verification). Reviewed 2026-10-16 by Codex; curation/card_evidence_reviews.json SHA-256 584f3e32ce0122eb2315fe09bbe22e058539bef184ad2d75756a6f3016bf2687.	ARO:3003317	not organism-specific	—	ARO:3003317 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Staphylococcus aureus gyrA conferring resistance to fluoroquinolones	ARO:3003296	not organism-specific	—	ARO:3003296 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Staphylococcus aureus parC conferring resistance to fluoroquinolones	ARO:3003312	not organism-specific	—	ARO:3003312 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Staphylococcus aureus parE conferring resistance to fluoroquinolones	ARO:3003315	not organism-specific	—	ARO:3003315 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Streptococcus pneumoniae parC conferring resistance to fluoroquinolones	ARO:3003311	not organism-specific	—	ARO:3003311 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Ureaplasma urealyticum gyrB conferring resistance to fluoroquinolones	ARO:3003305	not organism-specific	—	ARO:3003305 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)
Ureaplasma urealyticum parC conferring resistance to fluoroquinolones	ARO:3003309	not organism-specific	—	ARO:3003309 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 1

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
quinolone resistance protein (qnr)	ARO:3000419	not organism-specific	—	ARO:3000419 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000659 (gatifloxacin); 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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-26 · seed_from_sources
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-16 · seed_from_sources
Re-seeded; changed: resistance_mechanisms (CARD). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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