Sitafloxacin

CHEBI:4304 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Sitafloxacin is a fluoroquinolone active against multi-resistant Gram-positive and negative pathogens. Sitafloxacin shows inhibitory activity against DNA gyrase and topoisomerase IV, which blocks bacterial DNA replication, thereby causing double-stranded breaks in the bacterial chromosome. — PMID:21504249

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:26513
quinolone antibiotic CHEBI:86324
fluoroquinolone antibiotic CHEBI:87211
fluoroquinolone antibiotic ARO:0000001

Chemical structure

Computed structure properties
Molecular formula	C19H18ClF2N3O3
Charge	0
Average mass	409.82 Da
Monoisotopic mass	409.10048 Da
Source	ChEBI
InChIKey	PNUZDKCDAWUEGK-CYZMBNFOSA-N

SMILES

N[C@@H]1CN(c2c(F)cc3c(=O)c(C(=O)O)cn([C@@H]4C[C@@H]4F)c3c2Cl)CC12CC2

InChI

InChI=1S/C19H18ClF2N3O3/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28)/t10-,12+,13+/m0/s1

Also called

DU-6859 (EXACT_SYNONYM)— chebi
Sitafloxacin anhydrous (EXACT_SYNONYM)— chebi
gracevit (EXACT_SYNONYM)— chebi
sitafloxacin anhydrous (EXACT_SYNONYM)— chebi
sitafloxacin hydrate (EXACT_SYNONYM)— chebi
Gracevit (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.

drugcentral:2449

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:3003690`	sitafloxacin	`antibioticmech:aro-9220814bae`	2026-08-30
CHEBI	`CHEBI:4304`	Sitafloxacin	`antibioticmech:chebi-4fa641508a`	2026-08-30

Activity spectrum

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

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

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	—	0.0312 mg/L	—	CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; colourmetric	—	7 source isolates 7 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	0.0625 mg/L	—	CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; colourmetric	—	5 source isolates 5 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	0.125 mg/L	—	CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; colourmetric	—	6 source isolates 6 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	0.25 mg/L	—	CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; colourmetric	—	13 source isolates 13 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	0.5 mg/L	—	CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; colourmetric	—	5 source isolates 5 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; solid media; middlebrook; 7H10; critical concentration 2.0 mg/L	—	36 source isolates 36 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 3

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Neisseria gonorrhoeae gyrA with mutations conferring resistance to fluoroquinolones	ARO:3003928	not organism-specific	—	ARO:3003928 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003690 (sitafloxacin); database assertion, not a primary citation.)
Neisseria gonorrhoeae parC conferring resistance to fluoroquinolones	ARO:3003929	not organism-specific	—	ARO:3003929 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003690 (sitafloxacin); database assertion, not a primary citation.)
Pseudomonas aeruginosa gyrA conferring resistance to fluoroquinolones	ARO:3003684	not organism-specific	—	ARO:3003684 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003690 (sitafloxacin); 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 2026-09-10 · 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.

Provenance

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

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