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Compound Detail

CHEMBL59356

ATRELEUTON
🧪 Phase II
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🧪 Phase II
C[C@H](C#Cc1ccc(Cc2ccc(F)cc2)s1)N(O)C(N)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL59356
Name ATRELEUTON
Phase Phase II
Structure Type MOL
InChI Key MMSNEKOTSJRTRI-LLVKDONJSA-N

Known Names

A-85761 A-85761.0 ABBOTT-85761 ABT-761 Atreleuton VIA-2291
5
Targets
9
Activities
1
Assay Types
8
PK Parameters
20
Publications
6
Known Names
3
Indications
1
Mechanisms

Molecular Properties

318.4
MW (Da)
2.99
ALogP
3
HBA
2
HBD
66.6
PSA (Ų)
0.52
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -leuton
USAN Year 1997

Extended Properties

Molecular Formula C16H15FN2O2S
MW 318.37
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.29

Mechanism of Action

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

Indications

Acute Coronary Syndrome Atherosclerosis Coronary Disease

Activity Summary

IC50 9 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
 IC50 7.64 7.64 23.0 1
Homo sapiens
CHEMBL372
 IC50 7.64 7.23 23.0 2
RBL-1
CHEMBL614772
 IC50 7.64 7.64 23.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 7.05 6.8625 90.0 4
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 5.57 5.57 2700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 60.0 % Rattus norvegicus
F 100.0 % Mus musculus
F 90.0 % Cavia porcellus
F 95.0 % Canis lupus familiaris
F 90.0 % Macaca fascicularis
T1/2 15.0 hr -
T1/2 15.0 hr Simiiformes

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RBL-1 IC50 = 23.0 nM 7.64 Compound was tested for in vitro inhibition against broken RBL-1. 8709092
Homo sapiens IC50 = 23.0 nM 7.64 Compound was tested for in vitro inhibition against human PMNL. 8709092
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 23.0 nM 7.64 Inhibitory activity against 5-lipoxygenase obtained from rat basophilic leukemia... 9484493
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 90.0 nM 7.05 Inhibition of 5-LOX (unknown origin) expressed in Escherichia coli BL21-(DE3) pr... 33044073
Homo sapiens IC50 = 150.0 nM 6.82 Compound was tested for in vitro inhibition against human whole blood. 8709092
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 160.0 nM 6.8 5-lipoxygenase Inhibitory activity was measured by enzyme immunoassay using huma... 7490726
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 160.0 nM 6.8 In vitro inhibitory activity against 5-lipoxygenase in a human whole blood assay 15081022
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 160.0 nM 6.8 Inhibition of 5-lipoxygenase (5-LO) measured as LTB4 production in human whole b... 9207936
Bifunctional epoxide hydrolase 2 IC50 = 2700.0 nM 5.57 Inhibition of human sEH (1 to 555 residues) expressed in Escherichia coli BL21-(... 33044073

Literature References

PubMed DOI Target Context # Activities
7490726 10.1021/jm00024a004 ADMET 5
8709092 10.1021/jm960088k Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
9207936 10.1021/jm9700474 ADMET 2
9207936 10.1021/jm9700474 Polyunsaturated fatty acid 5-lipoxygenase 2
33044073 10.1021/acs.jmedchem.0c00561 No relevant target 1
8709092 10.1021/jm960088k RBL-1 1
33044073 10.1021/acs.jmedchem.0c00561 ADMET 1
33044073 10.1021/acs.jmedchem.0c00561 Polyunsaturated fatty acid 5-lipoxygenase 1
33044073 10.1021/acs.jmedchem.0c00561 Bifunctional epoxide hydrolase 2 1
30929436 10.1021/acs.jmedchem.8b02012 Homo sapiens 1
- 10.6019/CHEMBL3301361 ADMET 1
9207936 10.1021/jm9700474 Rattus norvegicus 1
15081022 10.1016/j.bmcl.2004.02.005 Polyunsaturated fatty acid 5-lipoxygenase 1
9484493 10.1021/jm970034q Polyunsaturated fatty acid 5-lipoxygenase 1
7490726 10.1021/jm00024a004 Monkey 1
7490726 10.1021/jm00024a004 Rattus norvegicus 1
7490726 10.1021/jm00024a004 Polyunsaturated fatty acid 5-lipoxygenase 1
8709092 10.1021/jm960088k ADMET 1
8709092 10.1021/jm960088k Cavia porcellus 1

Data from ChEMBL 36 via Core Engine