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Compound Detail

CHEMBL5315124

LEVOFLOXACIN
💊 Approved Drug
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💊 Approved Drug
C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23.C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23.O

Basic Information

ChEMBL ID CHEMBL5315124
Name LEVOFLOXACIN
Phase Approved
Structure Type MOL
InChI Key SUIQUYDRLGGZOL-RCWTXCDDSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL33
Active Moiety CHEMBL33

Known Names

Cravit DR-3355 Evoxil Iquix L-ofloxacin Levaquin Levofloxacin Levofloxacin (as hemihydrate) Levofloxacin hemihydrate Levofloxacin hydrate Nofaxin Ofloxacin s-(-)-form hemihydrate +7 more
21
Targets
57
Activities
2
Assay Types
30
PK Parameters
20
Publications
19
Known Names
20
Indications
2
Mechanisms

Molecular Properties

361.4
MW (Da)
1.54
ALogP
6
HBA
1
HBD
75.0
PSA (Ų)
0.87
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning
USAN Stem -oxacin
USAN Year 1996

Extended Properties

Molecular Formula C36H42F2N6O9
MW 740.76
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA gyrase inhibitor INHIBITOR DNA gyrase
Topoisomerase IV inhibitor INHIBITOR Topoisomerase IV

Indications

Bacterial Infections Bronchitis, Chronic Conjunctivitis, Bacterial Cystic Fibrosis Eye Infections Infections Pneumonia Respiratory Tract Infections Sinusitis Urinary Tract Infections Bronchitis Cataract Dyspepsia Endocarditis Fever Helicobacter Infections Hot Flashes Influenza, Human Maxillary Sinusitis Neutropenia

ATC Classification

J01MA12
levofloxacin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AE05
levofloxacin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 54 meas. best 6.9
EC50 3 meas. best 6.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Klebsiella pneumoniae
CHEMBL350
IC50 6.9 6.075 125.0 4
Staphylococcus aureus
CHEMBL352
IC50 6.9 6.178 125.0 5
Escherichia coli
CHEMBL354
IC50 6.9 5.8 125.0 3
Staphylococcus epidermidis
CHEMBL353
IC50 6.6 6.2 250.0 3
Unchecked
CHEMBL612545
IC50 6.43 6.295 370.0 2
Mycobacterium tuberculosis
CHEMBL360
IC50 6.23 5.9567 590.0 6
Streptococcus
CHEMBL612313
EC50 6.04 6.04 911.0 1
Enterococcus faecalis
CHEMBL362
IC50 6.0 6.0 1000.0 3
Streptokinase A
CHEMBL1293228
EC50 5.81 5.81 1546.0 1
Streptococcus sp. 'group A'
CHEMBL612389
EC50 5.68 5.68 2103.0 1
Replicase polyprotein 1ab
CHEMBL4295557
IC50 5.12 5.12 7600.0 1
Tubulin
CHEMBL2095182
IC50 4.95 4.95 11270.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 4.75 4.75 17900.0 1
MCF-10A
CHEMBL614321
IC50 4.6 4.6 25200.0 1
DNA gyrase subunit A
CHEMBL4165
IC50 4.28 4.28 52000.0 1
Enterococcus faecium
CHEMBL357
IC50 4.19 4.19 64000.0 3
LoVo
CHEMBL614721
IC50 4.17 4.17 67000.0 2
A549
CHEMBL392
IC50 4.17 4.165 67000.0 2
PC-3
CHEMBL390
IC50 4.17 4.17 67000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.17 4.17 67000.0 1
MCF7
CHEMBL387
IC50 4.17 4.17 67000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10.2 ug ml-1 -
AUC 6100.0 ng.hr.mL-1 Cavia porcellus
AUC 49800.0 ng.hr.mL-1 Mus musculus
AUC 64000.0 ng.hr.mL-1 Mus musculus
AUC 4.1 mg.hr/kg Mus musculus
AUC 4.1 mg.hr/kg Mus musculus
AUC 112400.0 ng.hr.mL-1 Callithrix jacchus
AUC 63600.0 ng.hr.mL-1 Callithrix jacchus
AUC 81400.0 ng.hr.mL-1 Callithrix jacchus
AUC 47.5 ng.hr.mL-1 Homo sapiens
AUC 56.3 ng.hr.mL-1 Homo sapiens
AUC 33.4 ng.hr.mL-1 Macaca mulatta
AUC 21.3 ng.hr.mL-1 Macaca mulatta
AUC 106000.0 ng.hr.mL-1 Rattus norvegicus
AUC 117000.0 ng.hr.mL-1 Rattus norvegicus
AUC 77000.0 ng.hr.mL-1 Rattus norvegicus
AUC 68000.0 ng.hr.mL-1 Rattus norvegicus
AUC 2500.0 ng.hr.mL-1 Mus musculus
AUC 11000.0 ng.hr.mL-1 Mus musculus
AUC 4000.0 ng.hr.mL-1 Mus musculus
AUC - - Mus musculus
AUC 15500.0 ng.hr.mL-1 Macaca fascicularis
AUC 15200.0 ng.hr.mL-1 Macaca fascicularis
AUC 19300.0 ng.hr.mL-1 Rattus norvegicus
AUC 16400.0 ng.hr.mL-1 Rattus norvegicus
AUC 5570.0 ng.hr.mL-1 Rattus norvegicus
AUC 3410.0 ng.hr.mL-1 Rattus norvegicus
AUC 27200.0 ng.hr.mL-1 Homo sapiens
AUC 47900.0 ng.hr.mL-1 Homo sapiens
AUC 48300.0 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 125.0 nM 6.9 Antibacterial activity against methicillin-sensitive Staphylococcus aureus 15 af... 24571273
Escherichia coli IC50 = 125.0 nM 6.9 Antibacterial activity against extended spectrum beta-lactamase-deficient Escher... 24571273
Klebsiella pneumoniae IC50 = 125.0 nM 6.9 Antibacterial activity against extended spectrum beta-lactamase-deficient Klebsi... 24571273
Staphylococcus aureus IC50 = 250.0 nM 6.6 Antibacterial activity against methicillin-sensitive Staphylococcus aureus ATCC ... 24571273
Staphylococcus aureus IC50 = 250.0 nM 6.6 Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC ... 24571273
Staphylococcus aureus IC50 = 250.0 nM 6.6 Antibacterial activity against methicillin-sensitive Staphylococcus aureus 12-28... 24571273
Staphylococcus epidermidis IC50 = 250.0 nM 6.6 Antibacterial activity against methicillin-sensitive Staphylococcus epidermidis ... 24571273
Staphylococcus epidermidis IC50 = 250.0 nM 6.6 Antibacterial activity against methicillin-sensitive Staphylococcus epidermidis ... 24571273
Klebsiella pneumoniae IC50 = 250.0 nM 6.6 Antibacterial activity against extended spectrum beta-lactamase-deficient Klebsi... 24571273
Unchecked IC50 = 370.0 nM 6.43 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Mycobacterium tuberculosis IC50 = 590.0 nM 6.23 Antitubercular activity against Mycobacterium tuberculosis H37Rv RIF-R1 harborin... 27437078
Mycobacterium tuberculosis IC50 = 600.0 nM 6.22 Antitubercular activity against Mycobacterium tuberculosis H37Rv RIF-R2 ATCC 358... 27437078
Mycobacterium tuberculosis IC50 = 640.0 nM 6.19 Antitubercular activity against Mycobacterium tuberculosis H37Rv INH-R1 harborin... 27437078
Unchecked IC50 = 690.0 nM 6.16 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Mycobacterium tuberculosis IC50 = 800.0 nM 6.1 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv after 6 days... 22036229
Mycobacterium tuberculosis IC50 = 840.0 nM 6.08 Antitubercular activity against Mycobacterium tuberculosis H37Rv INH-R2 ATCC 358... 27437078
Streptococcus EC50 = 911.0 nM 6.04 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Enterococcus faecalis IC50 = 1000.0 nM 6.0 Antibacterial activity against vancomycin-resistant Enterococcus faecalis ATCC 5... 24571273
Escherichia coli IC50 = 1000.0 nM 6.0 Antibacterial activity against extended spectrum beta-lactamase-deficient Escher... 24571273
Enterococcus faecalis IC50 = 1000.0 nM 6.0 Antibacterial activity against vancomycin-sensitive Enterococcus faecalis 12-5 a... 24571273

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 332
19364867 10.1128/aac.01252-08 Clostridioides difficile 83
17938189 10.1128/aac.01229-07 Streptococcus pneumoniae 77
19805554 10.1128/aac.00248-09 Pseudomonas aeruginosa 71
19188391 10.1128/aac.01133-08 Escherichia coli 64
21173174 10.1128/aac.00927-10 Escherichia coli 64
19307366 10.1128/aac.01531-08 Streptococcus pneumoniae 55
17876003 10.1128/aac.00827-07 Streptococcus pneumoniae 53
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44
18591275 10.1128/aac.01684-07 Acinetobacter baumannii 40
- 10.1007/s00044-012-0429-8 Staphylococcus aureus 39
18725440 10.1128/aac.00082-08 Streptococcus pneumoniae 38
20308374 10.1128/aac.01797-09 Streptococcus pneumoniae 38
17145801 10.1128/aac.01033-06 Burkholderia pseudomallei 37
17908940 10.1128/aac.00971-07 Streptococcus pneumoniae 34
18490500 10.1128/aac.01686-07 Escherichia coli 33
17296740 10.1128/aac.00646-06 Staphylococcus aureus 30
19884376 10.1128/aac.01123-09 Streptococcus pneumoniae 30
17220419 10.1128/aac.00959-06 Streptococcus pneumoniae 30
18809945 10.1128/aac.00707-08 Pseudomonas aeruginosa 28

Data from ChEMBL 36 via Core Engine