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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL33
CHEMBL33
Compound Name LEVOFLOXACIN
ChEMBL Synonyms DR-3355 | Floxacin | IQUIX | LEVAQUIN | TAVANIC | EVOXIL | RWJ-25213 | LEVOFLOXACIN | QUIXIN | OFTAQUIX | QUINSAIR
Max Phase 4 (Approved)
Trade Names Floxacin | IQUIX | LEVAQUIN | TAVANIC | EVOXIL | LEVOFLOXACIN | QUINSAIR | QUIXIN | OFTAQUIX
Molecular Formula C18H20FN3O4

Additional synonyms for CHEMBL33 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc4C(=O)C(=CN1c24)C(=O)O
Standard InChI InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8 ...
Download InChI
Standard InChI Key GSDSWSVVBLHKDQ-JTQLQIEISA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • MMV Pathogen Box
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL33

Molecule Features

CHEMBL33 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA gyrase inhibitor DNA gyrase DailyMed
Topoisomerase IV inhibitor Topoisomerase IV DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AppendicitisD001064EFO:0007149appendicitis2ClinicalTrials
Conjunctivitis, BacterialD003234EFO:1000829bacterial conjunctivitis2ClinicalTrials
Escherichia coli InfectionsD004927EFO:1001318Escherichia coli Infections1ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer2ClinicalTrials
SinusitisD012852EFO:0007486sinusitis3ClinicalTrials
CellulitisD002481EFO:0003035cellulitis2ClinicalTrials
Communicable DiseasesD003141EFO:0005741infectious disease3ClinicalTrials
Diabetic FootD017719EFO:1001459diabetic foot2ClinicalTrials
InfectionD007239EFO:0000544infection3ClinicalTrials
Kidney DiseasesD007674EFO:0003086kidney disease1ClinicalTrials
Skin DiseasesD012871EFO:0000701skin disease3ClinicalTrials
Urinary Bladder, OveractiveD053201EFO:1000781overactive bladder1ClinicalTrials
Bronchitis, ChronicD029481EFO:0006505chronic bronchitis3ClinicalTrials
Cystic FibrosisD003550Orphanet:586Cystic fibrosis3ClinicalTrials
EndocarditisD004696EFO:0000465endocarditis3ClinicalTrials
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
ProstatitisD011472EFO:0003830prostatitis3ClinicalTrials
Staphylococcal InfectionsD013203EFO:0005681Staphylococcus aureus infection3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
Maxillary SinusitisD015523EFO:0007361maxillary sinusitis3ClinicalTrials
Pelvic Inflammatory DiseaseD000292EFO:1001388Pelvic Inflammatory Disease3ClinicalTrials
SarcoidosisD012507Orphanet:797Sarcoidosis2ClinicalTrials
Urinary Tract InfectionsD014552EFO:0003103urinary tract infection3ClinicalTrials
Otitis MediaD010033EFO:0004992Otitis media3ClinicalTrials
PneumoniaD011014EFO:0003106pneumonia3ClinicalTrials
Pneumonia, BacterialD018410EFO:1001272bacterial pneumonia2ClinicalTrials
TuberculosisD014376Orphanet:3389Tuberculosis3ClinicalTrials
CataractD002386EFO:0001059cataract3ClinicalTrials
Helicobacter InfectionsD016481EFO:1000961Helicobacter pylori infectious disease3ClinicalTrials
Pulmonary Disease, Chronic ObstructiveD029424EFO:0000341chronic obstructive pulmonary disease2ClinicalTrials
Tuberculosis, Multidrug-ResistantD018088EFO:0007381multidrug-resistant tuberculosis2ClinicalTrials

Clinical Data

ClinicalTrials.gov LEVOFLOXACIN
The Cochrane Collaboration LEVOFLOXACIN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL33. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL262 Glycogen synthase kinase-3 beta Homo sapiens 0.990
CHEMBL2470 Cannabinoid CB2 receptor Rattus norvegicus 0.799

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL262 Glycogen synthase kinase-3 beta Homo sapiens 0.977
CHEMBL2470 Cannabinoid CB2 receptor Rattus norvegicus 0.950
CHEMBL2046259 Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Homo sapiens 0.828

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
361.4 361.1438 1.54 2 75.01 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 1 0 7 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
5.19 7.37 1.85 -.39 2 26 0.87

Structural Alerts

There are 2 structural alerts for CHEMBL33. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AE - Fluoroquinolones
S01AE05 - levofloxacin

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01M - QUINOLONE ANTIBACTERIALS
J01MA - Fluoroquinolones
J01MA12 - levofloxacin

ChemSpider ChemSpider:GSDSWSVVBLHKDQ-JTQLQIEISA-N
DailyMed levofloxacin
PubChem SID: 26719895 SID: 49665952
Wikipedia Levofloxacin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL33



ACToR 100986-85-4
BindingDB 50366826
Brenda 11274
ChEBI 63598
ChemicalBook CB4122906
DrugBank DB01137
DrugCentral 1569
eMolecules 494498
EPA CompTox Dashboard DTXSID0041060
FDA SRS RIX4E89Y14
Human Metabolome Database HMDB0001929
IBM Patent System CF6AB0C2EB7936E005A5D09A38C60FDE
KEGG Ligand C07660
LINCS LSM-5270
Mcule MCULE-2011834955 MCULE-1927163841
MolPort MolPort-002-885-835
NIH Clinical Collection SAM001246758
Nikkaji J142.436J
PDBe LFX
PharmGKB PA450214
PubChem 149096 6956357
PubChem: Drugs of the Future 12014081
PubChem: Thomson Pharma 14901428 14876841
Selleck Levofloxacin(Levaquin)
SureChEMBL SCHEMBL15397
ZINC ZINC000000538273

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/GSDSWSVVBLHKDQ-JTQLQIEISA-N spacer
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