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.
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
Equivalent identifiers for this same structure in other resources.
Activity roles
Every antimicrobial role a source asserts for this compound — the
unreduced evidence behind its antimicrobial_class.
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 |
Resistance mechanisms
3 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 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
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.