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Compound Detail

CHEMBL93

ZILEUTON
💊 Approved Drug
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💊 Approved Drug
CC(c1cc2ccccc2s1)N(O)C(N)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL93
Name ZILEUTON
Phase Approved
Structure Type MOL
InChI Key MWLSOWXNZPKENC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

A-64077 ABBOTT-64077 NSC-730712 NSC-759277 Zileuton Zyflo Zyflo cr
18
Targets
169
Activities
3
Assay Types
9
PK Parameters
20
Publications
7
Known Names
9
Indications
1
Mechanisms

Molecular Properties

236.3
MW (Da)
2.73
ALogP
3
HBA
2
HBD
66.6
PSA (Ų)
0.62
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -leuton
USAN Year 1990

Extended Properties

Molecular Formula C11H12N2O2S
MW 236.30
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -0.23

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Arachidonate 5-lipoxygenase inhibitor INHIBITOR Polyunsaturated fatty acid 5-lipoxygenase ✓ ✓

Indications

Asthma Pulmonary Disease, Chronic Obstructive Acne Vulgaris Idiopathic Pulmonary Fibrosis Lung Neoplasms Tobacco Use Disorder Anemia, Sickle Cell Leukemia, Myelogenous, Chronic, BCR-ABL Positive Inflammation

Activity Summary

IC50 166 meas. best 8.7
EC50 2 meas. best 6.33
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Homo sapiens
CHEMBL372
 IC50 8.7 5.9788 2.0 16
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
 IC50 7.41 5.7321 38.9 14
RBL-1
CHEMBL614772
 IC50 7.0 7.0 100.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
 IC50 6.85 6.2094 140.0 18
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 6.82 5.9245 150.0 96
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL5211
 IC50 6.72 6.72 190.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL2903
 IC50 6.4 5.605 400.0 2
Leukotriene B4 receptor 1
CHEMBL3911
 IC50 6.38 6.38 420.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 EC50 6.33 6.33 470.0 1
MC9
CHEMBL614867
 IC50 6.26 6.26 550.0 1
Arachidonate 5-lipoxygenase-activating protein
CHEMBL4550
 IC50 6.24 5.76 580.0 3
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 6.23 6.23 591.0 1
Prostaglandin E synthase
CHEMBL5658
 IC50 6.22 6.22 600.0 1
Leukotriene A-4 hydrolase
CHEMBL4618
 IC50 6.07 6.07 850.0 1
Mus musculus
CHEMBL375
 IC50 5.92 5.37 1200.0 3
Mus musculus
CHEMBL375
 EC50 5.8 5.8 1600.0 1
Rattus norvegicus
CHEMBL376
 IC50 5.7 5.15 2000.0 2
Protein-lysine 6-oxidase
CHEMBL2249
 IC50 5.46 5.46 3500.0 1
Polyunsaturated fatty acid lipoxygenase ALOX12
CHEMBL3687
 IC50 4.26 4.26 55000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.76 uL.min-1.(10^6cells)-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Macaca fascicularis
Ka 0.26 10'4 /uL Homo sapiens
T1/2 3.0 hr -
T1/2 0.4 hr Simiiformes
T1/2 0.44 hr Simiiformes
T1/2 1.0 hr Macaca mulatta
T1/2 3.0 hr Homo sapiens
T1/2 0.4 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Homo sapiens IC50 = 2.0 nM 8.7 Effect on production of LTB4 in human whole blood 8164257
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Antileukotrienic activity in rat polymorphonuclear cells assessed as inhibition ... 17448575
Unchecked IC50 = 38.91 nM 7.41 Inhibition of soyabean 15-LOX preincubated for 5 mins followed by susbtrate addi... 31299586
RBL-1 IC50 = 100.0 nM 7.0 Compound was tested for in vitro inhibition on broken RBL-1. 8709092
Unchecked IC50 = 139.1 nM 6.86 Inhibition of soybean 5-LOX 35931005
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 140.0 nM 6.85 Inhibition of 5-Lipoxygenase of rat basophilic leukemia cells -
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 150.0 nM 6.82 Inhibition of human 5-lipoxygenase using arachidonic acid as substrate pretreate... 30025348
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 150.0 nM 6.82 Inhibition of human 5-Lipoxygenase using H2DCFDA as substrate preincubated for 5... 32018096
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 180.0 nM 6.75 Inhibition of rat 5-LOX expressed in Sf21 insect cells preincubated for 4 mins f... 30108915
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 190.0 nM 6.72 Inhibition of 5-LO in mouse BMM cells assessed as formation of LTC4 after 30 min... 26432605
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 200.0 nM 6.7 Compound was tested for its inhibitory activity against 5-lipoxygenase in rat. -
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 300.0 nM 6.52 Inhibition of 5-LOX (unknown origin) using arachidonic acid as substrate after 5... 24508141
Unchecked IC50 = 300.0 nM 6.52 Inhibition of soyabean 5-LOX using arachidonic acid as substrate by microplate s... 25956953
Unchecked IC50 = 300.0 nM 6.52 Inhibition of soybean LOX using arachidonic acid as substrate incubated for 5 mi... 34137625
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 300.0 nM 6.52 Inhibition of 5-LOX (unknown orgin) using arachidonic acid as substrate incubate... 37591315
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 320.0 nM 6.5 The compound was tested for its inhibitory activity against arachidonic acid in ... 1313879
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 320.0 nM 6.5 Inhibition of calcium ionophore (A-23187)-stimulated LTB4 formation in human neu... 10691695
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 350.0 nM 6.46 Inhibition of human recombinant 5-LOX assessed as reduction in leukotriene B4 pr... 28322565
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 370.0 nM 6.43 In vitro inhibition of 5-lipoxygenase (5-HETE) derived from the 9000xg supernata... 7932593
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 390.0 nM 6.41 Inhibition of 5-LOX (unknown origin) 36481449

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 326
16472241 10.2174/1570163043334794 Hepatotoxicity 18
7837242 10.1021/jm00001a012 Polyunsaturated fatty acid 5-lipoxygenase 17
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
8978834 10.1021/jm960271d Mus musculus 7
36318728 10.1021/acs.jmedchem.2c00817 Mus musculus 7
37976708 10.1016/j.ejmech.2023.115932 Polyunsaturated fatty acid 5-lipoxygenase 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
24697244 10.1021/jm401740w Polyunsaturated fatty acid 5-lipoxygenase 6
7861415 10.1021/jm00004a013 Cavia porcellus 6
23871907 10.1016/j.ejmech.2013.06.039 Polyunsaturated fatty acid 5-lipoxygenase 6
22449023 10.1021/jm201687d 5-lipoxygenase/FLAP 5
18498150 10.1021/jm701467e MC9 5
8246226 10.1021/jm00075a013 Polyunsaturated fatty acid 5-lipoxygenase 4
8246226 10.1021/jm00075a013 Leukotriene B4 receptor 1 4
26290290 10.1021/acs.jmedchem.5b01011 Polyunsaturated fatty acid 5-lipoxygenase 4
24871899 10.1016/j.ejmech.2014.05.033 Polyunsaturated fatty acid 5-lipoxygenase 4
30638966 10.1016/j.bmc.2018.12.043 Polyunsaturated fatty acid 5-lipoxygenase 4

Data from ChEMBL 36 via Core Engine