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Compound Detail

CHEMBL316040

TEPOXALIN
🧪 Phase II
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🧪 Phase II
COc1ccc(-n2nc(CCC(=O)N(C)O)cc2-c2ccc(Cl)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL316040
Name TEPOXALIN
Phase Phase II
Structure Type MOL
InChI Key XYKWNRUXCOIMFZ-UHFFFAOYSA-N

Known Names

ORF 20485 ORF-20485 RWJ 20485 RWJ-20485 Tepoxalin Tepoxalina Tepoxaline Zubrin
7
Targets
17
Activities
2
Assay Types
0
PK Parameters
17
Publications
8
Known Names
3
Mechanisms

Molecular Properties

385.9
MW (Da)
3.98
ALogP
5
HBA
1
HBD
67.6
PSA (Ų)
0.51
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Year 1987

Extended Properties

Molecular Formula C20H20ClN3O3
MW 385.85
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.16

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase-1 inhibitor INHIBITOR Prostaglandin G/H synthase 1 ✓ ✓
Cyclooxygenase-2 inhibitor INHIBITOR Cyclooxygenase-2 ✓ ✓
Arachidonate 5-lipoxygenase inhibitor INHIBITOR Arachidonate 5-lipoxygenase ✓ ✓

Activity Summary

IC50 15 meas. best 6.82
EC50 2 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 EC50 7.16 7.16 70.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL312
 IC50 6.82 6.47 150.0 3
Unchecked
CHEMBL612545
 IC50 6.82 5.7943 150.0 7
Cyclooxygenase
CHEMBL2095157
 IC50 5.54 5.46 2850.0 2
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 5.54 5.54 2850.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.54 5.44 2850.0 2
Mus musculus
CHEMBL375
 EC50 4.35 4.35 44500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Polyunsaturated fatty acid 5-lipoxygenase EC50 = 70.0 nM 7.16 In vitro inhibition of ionophore stimulated LTB4 release from human peripheral b... 1324317
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 150.0 nM 6.82 Inhibitory activity against 5-lipoxygenase (5-LO) in intact rat barophilic leuke... 10230624
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 150.0 nM 6.82 The compound was tested for inhibitory activity against 5-Lipoxygenase in rat RB... 1635053
Unchecked IC50 = 150.0 nM 6.82 Inhibition of soybean LOX using arachidonic acid as substrate incubated for 5 mi... 34137625
Unchecked IC50 = 661.5 nM 6.18 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1700.0 nM 5.77 Inhibitory activity against 5-lipoxygenase (5-LO) using broken rat barophilic le... 10230624
Unchecked IC50 = 1747.9 nM 5.76 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 2075.7 nM 5.68 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 2812.4 nM 5.55 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Cyclooxygenase IC50 = 2850.0 nM 5.54 Inhibitory activity against cyclooxygenase (COX) in intact rat barophilic leukem... 10230624
Prostaglandin G/H synthase 1 IC50 = 2850.0 nM 5.54 Inhibition of ovine COX-1 using arachidonic acid as substrate preincubated for 1... 34137625
Prostaglandin G/H synthase 2 IC50 = 2850.0 nM 5.54 Inhibition of human COX-2 using arachidonic acid as substrate preincubated for 1... 34137625
Unchecked IC50 = 4107.6 nM 5.39 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Cyclooxygenase IC50 = 4200.0 nM 5.38 Inhibitory activity against Cyclooxygenase (COX) using broken rat barophilic leu... 10230624
Prostaglandin G/H synthase 1 IC50 = 4600.0 nM 5.34 Inhibitory activity against Cyclooxygenase using sheep seminal vesicle (SSV) enz... 10230624
Unchecked IC50 = 6545.3 nM 5.18 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Mus musculus EC50 = 44500.0 nM 4.35 In vivo 5-Lipoxygenase inhibitory activity by using mouse zymosan peritonitis mo... 1324317

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
10230624 10.1016/s0960-894x(99)00117-1 Cyclooxygenase 2
10230624 10.1016/s0960-894x(99)00117-1 Polyunsaturated fatty acid 5-lipoxygenase 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
34137625 10.1021/acs.jmedchem.1c00880 Prostaglandin G/H synthase 2 1
10230624 10.1016/s0960-894x(99)00117-1 Prostaglandin G/H synthase 1 1
34137625 10.1021/acs.jmedchem.1c00880 Prostaglandin G/H synthase 1 1
34137625 10.1021/acs.jmedchem.1c00880 Unchecked 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
1324317 10.1021/jm00095a012 Mus musculus 1
1324317 10.1021/jm00095a012 Polyunsaturated fatty acid 5-lipoxygenase 1
1635053 10.1021/jm00092a001 Polyunsaturated fatty acid 5-lipoxygenase 1

Data from ChEMBL 36 via Core Engine