levofloxacin
An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.
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
-
CHEBI:194135 - quinolone antibiotic
CHEBI:86324 - fluoroquinolone antibiotic
CHEBI:87211 - fluoroquinolone antibiotic
ARO:0000001
Chemical structure
| Molecular formula | C18H20FN3O4 |
|---|---|
| Charge | 0 |
| Average mass | 361.373 Da |
| Monoisotopic mass | 361.14378 Da |
| Source | ChEBI |
| InChIKey | GSDSWSVVBLHKDQ-JTQLQIEISA-N |
C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
Also called
- levofloxacine
- levofloxacino
- levofloxacinum
- (3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
- (-)-Ofloxacin
- (3S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid
- (S)-(-)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzooxazine-6-carboxylic acid
- (S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid
- (S)-ofloxacin
- (−)-ofloxacin
- DR 3355
- DR-3355
- L-ofloxacin
- Ofloxacin S-(-)-form
- S-(−)-ofloxacin
- Levaquin
- Tavanic
Cross-references
- levofloxacin
ARO:0000071 - cas:100986-85-4
- hmdb:HMDB0001929
- kegg.compound:C07660
- lincs.smallmolecule:LSM-5270
- pdb-ccd:LFX
- reaxys:5385660
- vsdb:1899
- chembl:CHEMBL5315124
- pubchem.compound:149096
Drug registries
Patents and articles
Activity roles
- antimicrobial agent
CHEBI:33281 - antibacterial drug
CHEBI:36047
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:0000071 |
levofloxacin | antibioticmech:aro-825bdb3c2e |
2026-08-30 |
| CHEBI | CHEBI:63598 |
levofloxacin | antibioticmech:chebi-a88ec56d37 |
2026-08-30 |
Molecular targets
fluoroquinolone sensitive gyrA PROTEIN DIRECT_BINDING_TARGET
Fluoroquinolone sensitive parC PROTEIN DIRECT_BINDING_TARGET
Mechanism summary
- Mode of action
- NUCLEIC_ACID_SYNTHESIS_INHIBITION microbial target
Activity spectrum
| Organism | Activity | MIC | Disk diffusion | Assay | Strain | Sample/genome | Evidence |
|---|---|---|---|---|---|---|---|
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960 | — |
59 source isolates 59 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960 | — |
104 source isolates 104 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | INTERMEDIATE | — | — | CRyPTIC DST; CLIRES2020; solid media | — |
1 source isolates 1 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2020; solid media | — |
109 source isolates 109 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2020; solid media | — |
657 source isolates 657 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 | — |
24 source isolates 24 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 | — |
23 source isolates 23 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | INTERMEDIATE | — | — | CRyPTIC DST; CLIRES2023; solid media | — |
2 source isolates 2 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2023; solid media | — |
116 source isolates 116 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; CLIRES2023; solid media | — |
692 source isolates 692 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.25 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
1230 source isolates 1230 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.25 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
185 source isolates 185 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.25 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
344 source isolates 344 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.5 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
2447 source isolates 2447 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.5 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
169 source isolates 169 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 0.5 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
411 source isolates 411 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 1.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
325 source isolates 325 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 1.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
63 source isolates 63 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | 1.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
50 source isolates 50 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | 2.0 mg/L | — | CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L | — |
143 source isolates 143 measurements |
EvidencePage data (JSON.gz) |
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 30
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Acinetobacter baumannii gyrA conferring resistance to fluoroquinolones | ARO:3003817 | — | ||
| Acinetobacter baumannii parC conferring resistance to fluoroquinolones | ARO:3003818 | — | ||
| Bartonella bacilliformis gyrA conferring resistance to fluoroquinolones | ARO:3003297 | — | ||
| Capnocytophaga gingivalis gyrA conferring resistance to fluoroquinolones | ARO:3003931 | — | ||
| Clostridioides difficile gyrA conferring resistance to fluoroquinolones | ARO:3003995 | — | ||
| Clostridioides difficile gyrB conferring resistance to fluoroquinolones | ARO:3004562 | — | ||
| Cutibacterium acnes gyrA conferring resistance to fluoroquinolones | ARO:3003974 | — | ||
| Escherichia coli gyrA conferring resistance to fluoroquinolones | ARO:3003294 | — | ||
| Escherichia coli parC conferring resistance to fluoroquinolones | ARO:3003308 | — | ||
| Escherichia coli parE conferring resistance to fluoroquinolones | ARO:3003316 | — | ||
| Helicobacter pylori gyrA conferring resistance to fluoroquinolones | ARO:3007052 | — | ||
| Helicobacter pylori gyrB conferring resistance to fluoroquinolones | ARO:3007053 | — | ||
| Morganella morganii gyrB conferring resistance to fluoroquinolones | ARO:3003306 | — | ||
| Mycobacterium avium gyrA with mutation conferring resistance to fluoroquinolone | ARO:3007473 | — | ||
| Mycobacterium leprae gyrA conferring resistance to fluoroquinolones | ARO:3003298 | — | ||
| Mycobacterium leprae gyrB conferring resistance to fluoroquinolones | ARO:3003304 | — | ||
| Mycobacterium tuberculosis gyrA conferring resistance to fluoroquinolones | ARO:3003295 | — | ||
| Mycobacterium tuberculosis gyrA mutations conferring resistance to levofloxacin | ARO:3007809 | — | ||
| Mycobacterium tuberculosis gyrB mutations conferring resistance to levofloxacin | ARO:3007810 | — | ||
| Mycobacterium tuberculosis gyrB with mutation conferring resistance to fluoroquinolones | ARO:3003459 | — | ||
| Mycoplasma hominis parC conferring resistance to fluoroquinolones | ARO:3003310 | — | ||
| Pseudomonas aeruginosa gyrA conferring resistance to fluoroquinolones | ARO:3003684 | — | ||
| Salmonella serovars gyrB conferring resistance to fluoroquinolones | ARO:3003307 | — | ||
| Salmonella serovars parE conferring resistance to fluoroquinolones |
ARO:3003317 | — | ||
| Staphylococcus aureus gyrA conferring resistance to fluoroquinolones | ARO:3003296 | — | ||
| Staphylococcus aureus parC conferring resistance to fluoroquinolones | ARO:3003312 | — | ||
| Staphylococcus aureus parE conferring resistance to fluoroquinolones | ARO:3003315 | — | ||
| Streptococcus pneumoniae parC conferring resistance to fluoroquinolones | ARO:3003311 | — | ||
| Ureaplasma urealyticum gyrB conferring resistance to fluoroquinolones | ARO:3003305 | — | ||
| Ureaplasma urealyticum parC conferring resistance to fluoroquinolones | ARO:3003309 | — |
ANTIBIOTIC_EFFLUX 3
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Acinetobacter baumannii AbaQ | ARO:3004574 | — | ||
| QepA3 | ARO:3004378 | — | ||
| Rv1877 | ARO:3007662 | — |
ANTIBIOTIC_TARGET_PROTECTION 1
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| quinolone resistance protein (qnr) | ARO:3000419 | — |
ANTIBIOTIC_TARGET_REPLACEMENT 1
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Helicobacter pylori rpoB mutation conferring resistance to rifampicin | ARO:3007051 | — |
Causal graphs
Levofloxacin poisons bacterial topoisomerase IV MECHANISTIC
Levofloxacin stabilizes a bacterial topoisomerase IV-DNA cleavage complex, blocking resealing of the enzyme-linked DNA break and disrupting chromosome topology control.
| Node | Label | Type | Grounding |
|---|---|---|---|
levofloxacin |
levofloxacin | COMPOUND | CHEBI:63598 |
topoisomerase_iv |
bacterial topoisomerase IV |
GENE_OR_PROTEIN | ARO:3000735 |
topoiv_dna_cleavage_complex |
topoisomerase IV covalent DNA cleavage complex | STATE | REVIEWED_LABEL_ONLY |
dna_religation |
topoisomerase IV DNA religation | MOLECULAR_FUNCTION | REVIEWED_LABEL_ONLY |
dna_topology_control |
bacterial chromosome decatenation and topology control | BIOLOGICAL_PROCESS | REVIEWED_LABEL_ONLY |
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
levofloxacin |
stabilizes | topoiv_dna_cleavage_complex |
|
topoisomerase_iv |
participates in | topoiv_dna_cleavage_complex |
|
topoiv_dna_cleavage_complex |
inhibits | dna_religation |
|
dna_religation |
supports | dna_topology_control |
Curation history
-
SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO, CHEBI)
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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CURATED_CAUSAL_GRAPH
Added a PMID-supported causal graph for levofloxacin poisoning of bacterial topoisomerase IV.
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank levofloxacin-resistant Escherichia coli isolate MIC observation.
-
CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank levofloxacin-resistant Klebsiella pneumoniae isolate MIC observation.
-
CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank levofloxacin-resistant Acinetobacter baumannii isolate MIC observation.
-
CURATED_RESISTANT_TAXA
Corrected the CDC/FDA AR Isolate Bank 0349 breakpoint context from CLSI 2024 M100 S34 to CLSI 2025 M100 S35.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank levofloxacin-resistant Escherichia coli MIC observation from isolate 0346.
-
CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank levofloxacin-resistant Escherichia coli isolate MIC observation for AR-1305.
-
CURATED_RESISTANT_TAXA
Added 13 stable-URL CDC/FDA AR Isolate Bank levofloxacin-resistant Multi-Mechanism panel MIC observations for AR-1149, AR-1150, AR-1152, AR-1153, AR-1155, AR-1156, AR-1157, AR-1158, AR-1159, AR-1160, AR-1161, AR-1162, and AR-1163.
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CURATED_RESISTANT_TAXA
Added five stable-URL CDC/FDA AR Isolate Bank Panel 1125 levofloxacin-resistant Staphylococcus MIC observations for AR-0701, AR-0702, AR-0726, AR-0729, and AR-0730.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Enterococcus faecalis MIC observation for AR-0780.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1106.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1107.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1268.
-
CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1269.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1270.
-
CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1328.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Escherichia coli MIC observation for AR-0495.
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CURATED_RESISTANT_TAXA
Added CDC/FDA AR Isolate Bank Panel 1227 isolate 0033 Acinetobacter baumannii levofloxacin MIC 8 mg/L with interpretation R; preserved source Unknown, BioSample SAMN04014874, Study ID CarbaNP-02, and MLST ST85(Pasteur)/ST1089(Oxford) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 levofloxacin-resistant Acinetobacter baumannii MIC observation for AR-0078; preserved source Pus, BioSample SAMN04014919, Study ID CarbaNP-47, and MLST ST229(Pasteur)/ST203(Oxford) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 levofloxacin-resistant Acinetobacter baumannii MIC observation for AR-0083; preserved source Unknown, BioSample SAMN04014924, Study ID CarbaNP-52, and MLST ST1(Pasteur)/ST231/1604(Oxford) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Enterococcus faecium MIC observation for AR-0500; preserved source Blood, BioSample SAMN11953784, and Study ID NEW-13 in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 levofloxacin-resistant Escherichia coli MIC observation for AR-0538; preserved BioSample SAMN11953785 and Study ID NEW-22 in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1394 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1332; preserved source Urine, Study ID IMP-10, unavailable BioSample accession, and MLST ST357(Pasteur) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1394 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1333; preserved source Urine, Study ID IMP-11, unavailable BioSample accession, and MLST ST2731(Pasteur) in evidence notes.
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CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1394 levofloxacin-resistant Pseudomonas aeruginosa MIC observation for AR-1334; preserved source P-trap water, Study ID IMP-12, unavailable BioSample accession, and MLST ST235(Pasteur) in evidence notes.
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STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS
Structured BioSample accessions on 35 activity_spectrum observation(s) where evidence notes already named exactly one accession.
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RESEEDED_FROM_SOURCES
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
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RESEEDED_FROM_SOURCES
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
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RESEEDED_FROM_SOURCES
Re-seeded; changed: resistance_mechanisms (CARD). Upstream retrieval date 2026-08-30, unchanged.
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CURATED_UNIPROT_PROTEIN_EXAMPLES
Added curated S. pneumoniae TIGR4 ParC (P72525) and E. coli K-12 ParC/ParE (P0AFI2, P20083) UniProtKB protein examples on the levofloxacin topoisomerase_iv causal graph node.