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Compound Detail

CHEMBL126

LINEZOLID
💊 Approved Drug
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💊 Approved Drug
CC(=O)NC[C@H]1CN(c2ccc(N3CCOCC3)c(F)c2)C(=O)O1

Basic Information

ChEMBL ID CHEMBL126
Name LINEZOLID
Phase Approved
Structure Type MOL
InChI Key TYZROVQLWOKYKF-ZDUSSCGKSA-N
Therapeutic ✓ Yes

Known Names

Linezolid Linezolide Pnu-100766 U-100,766 U-100766 Zyvox
16
Targets
53
Activities
3
Assay Types
30
PK Parameters
20
Publications
6
Known Names
20
Indications
1
Mechanisms

Molecular Properties

337.4
MW (Da)
1.12
ALogP
5
HBA
1
HBD
71.1
PSA (Ų)
0.89
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral
USAN Stem -zolid
USAN Year 1997

Extended Properties

Molecular Formula C16H20FN3O4
MW 337.35
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -1.82

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial 70S ribosome inhibitor INHIBITOR Bacterial 70S ribosome

Indications

Bacteremia Bacterial Infections Infections Osteomyelitis Pneumonia Abscess Cellulitis Gram-Positive Bacterial Infections Optic Nerve Diseases Pneumonia, Bacterial Pneumonia, Pneumococcal Skin Diseases Staphylococcal Infections Syphilis Tuberculosis Tuberculosis, Pulmonary Cystic Fibrosis Hematologic Neoplasms Lung Diseases Meningitis

ATC Classification

J01XX08
linezolid
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 45 meas. best 6.96
EC50 4 meas. best 6.8
Ki 4 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Clostridioides difficile
CHEMBL614965
IC50 6.96 6.96 110.0 1
Streptokinase A
CHEMBL1293228
EC50 6.8 6.01 158.0 2
Streptococcus sp. 'group A'
CHEMBL612389
EC50 6.77 6.77 170.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
IC50 6.21 5.646 619.0 5
Streptococcus
CHEMBL612313
EC50 6.19 6.19 645.0 1
Unchecked
CHEMBL612545
IC50 6.05 5.17 900.0 5
Escherichia coli
CHEMBL354
IC50 6.02 5.3558 950.0 12
Pseudomonas aeruginosa
CHEMBL348
IC50 5.77 4.97 1700.0 4
Acinetobacter baumannii
CHEMBL614425
IC50 5.4 5.0575 4000.0 4
Amine oxidase [flavin-containing] A
CHEMBL1951
IC50 5.19 4.855 6520.0 4
Amine oxidase [flavin-containing] A
CHEMBL1951
Ki 5.1 4.585 7900.0 4
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial
CHEMBL5758
IC50 5.09 5.09 8190.0 1
Prostaglandin G/H synthase 1
CHEMBL221
IC50 5.09 5.09 8190.0 1
H9c2
CHEMBL614576
IC50 5.06 5.06 8710.0 1
Calmodulin-like protein 3
CHEMBL5169127
IC50 5.03 5.03 9300.0 1
Rattus norvegicus
CHEMBL376
IC50 4.92 4.92 12000.0 1
Amine oxidase [flavin-containing] B
CHEMBL2993
IC50 4.77 4.77 17000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4240.0 ng.hr.mL-1 Rattus norvegicus
AUC 29090.0 ng.hr.mL-1 Mus musculus
AUC 112020.0 ng.hr.mL-1 Mus musculus
AUC 45700000000.0 ng.hr.mL-1 Mus musculus
AUC 105000000000.0 ng.hr.mL-1 Mus musculus
AUC 105000.0 ng.hr.mL-1 Rattus norvegicus
AUC 666000.0 ng.hr.mL-1 Rattus norvegicus
AUC 260000.0 ng.hr.mL-1 Homo sapiens
AUC 10980.0 ng.hr.mL-1 Mus musculus
AUC 780.0 ng.hr.mL-1 Mus musculus
AUC 76300.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 136900.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 173000.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 334000.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 87800.0 ng.hr.mL-1 Cavia porcellus
AUC 118700.0 ng.hr.mL-1 Cavia porcellus
AUC 125800.0 ng.hr.mL-1 Cavia porcellus
AUC 84600.0 ng.hr.mL-1 Homo sapiens
AUC 96800.0 ng.hr.mL-1 Homo sapiens
AUC 124500.0 ng.hr.mL-1 Homo sapiens
AUC 136400.0 ng.hr.mL-1 Homo sapiens
AUC 60100.0 ng.hr.mL-1 Homo sapiens
AUC 66800.0 ng.hr.mL-1 Homo sapiens
AUC 80300.0 ng.hr.mL-1 Homo sapiens
AUC 160700.0 ng.hr.mL-1 Homo sapiens
AUC 2100.0 ng.hr.mL-1 Mus musculus
AUC 16000.0 ng.hr.mL-1 Mus musculus
AUC 19000.0 ng.hr.mL-1 Mus musculus
AUC 196080.0 ng.hr.mL-1 Homo sapiens
AUC 412550.0 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Clostridioides difficile IC50 = 110.0 nM 6.96 Antibacterial activity against Clostridioides difficile assessed as inhibition o... 38753983
Streptokinase A EC50 = 158.0 nM 6.8 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus sp. 'group A' EC50 = 170.0 nM 6.77 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Amine oxidase [flavin-containing] B IC50 = 619.0 nM 6.21 Inhibition of recombinant MAO-B (unknown origin) using benzylamine as a substrat... 38116435
Amine oxidase [flavin-containing] B IC50 = 619.0 nM 6.21 Inhibition of human recombinant MAO-B using benzylamine as substrate 38894926
Streptococcus EC50 = 645.0 nM 6.19 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Unchecked IC50 = 900.0 nM 6.05 Inhibition of 50S ribosomal subunit purified from Staphylococcus aureus ATCC 292... 18663023
Escherichia coli IC50 = 950.0 nM 6.02 Inhibition of transcription and translation activity in Escherichia coli by luci... 17562363
Escherichia coli IC50 = 950.0 nM 6.02 Inhibition of transcription and translation activity in Escherichia coli by luci... 17590334
Pseudomonas aeruginosa IC50 = 1700.0 nM 5.77 Antibacterial activity against efflux pump lacking/recombinant OM pore producing... 36257060
Amine oxidase [flavin-containing] B IC50 = 2100.0 nM 5.68 Reversible inhibition of human MAO-B 26536532
Unchecked IC50 = 2400.0 nM 5.62 Inhibition of Escherichia coli switch region of RNA polymerase after 1 hr by tra... 25798859
Escherichia coli IC50 = 3300.0 nM 5.48 Antibacterial activity against Escherichia coli by transcription and translation... 16901693
Escherichia coli IC50 = 3600.0 nM 5.44 Inhibition of protein synthesis in Escherichia coli by cell-free transcription-t... 17988109
Escherichia coli IC50 = 3600.0 nM 5.44 Antibacterial activity against Escherichia coli by transcription-translation ass... 19064317
Acinetobacter baumannii IC50 = 4000.0 nM 5.4 Antibacterial activity against efflux pump lacking/recombinant OM pore producing... 36257060
Escherichia coli IC50 = 4100.0 nM 5.39 In vitro inhibitory activity against protein synthesis was determined by transcr... 14623007
Amine oxidase [flavin-containing] B IC50 = 4336.0 nM 5.36 Inhibition of MAO-B (unknown origin) preincubated with compound for 15 mins foll... 38761790
Escherichia coli IC50 = 4600.0 nM 5.34 Inhibition of protein synthesis in Escherichia coli S30 extract by translation a... 18951792
Escherichia coli IC50 = 4600.0 nM 5.34 Inhibition of Escherichia coli translation 18947996

Literature References

PubMed DOI Target Context # Activities
19433566 10.1128/aac.00183-09 Staphylococcus aureus 112
19581457 10.1128/aac.00908-08 NON-PROTEIN TARGET 108
20100878 10.1128/aac.01022-09 Enterococcus faecalis 93
18458134 10.1128/aac.01439-07 Bacillus anthracis 89
17875997 10.1128/aac.00550-07 Staphylococcus aureus 84
20404122 10.1128/aac.01516-09 Staphylococcus aureus 58
18710909 10.1128/aac.00676-08 Staphylococcus aureus 55
20100878 10.1128/aac.01022-09 ADMET 54
19546358 10.1128/aac.00206-09 Staphylococcus aureus 54
20145088 10.1128/aac.01350-09 Staphylococcus aureus 51
38761790 10.1016/j.ejmech.2024.116493 ADMET 47
17210770 10.1128/aac.01496-06 NON-PROTEIN TARGET 46
20385852 10.1128/aac.01724-09 Staphylococcus aureus 46
20176900 10.1128/aac.01653-09 Staphylococcus aureus 45
20308374 10.1128/aac.01797-09 Streptococcus pneumoniae 41
24694071 10.1021/jm401931e Staphylococcus aureus 39
20585126 10.1128/aac.00452-10 Staphylococcus aureus 38
17606686 10.1128/aac.01567-06 Staphylococcus aureus 38
19188385 10.1128/aac.01619-08 Staphylococcus aureus 37
20231392 10.1128/aac.01569-09 Staphylococcus aureus 30

Data from ChEMBL 36 via Core Engine