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Compound Detail

CHEMBL3989929

AZELIRAGON
🧪 Phase III
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🧪 Phase III
CCCCc1nc(-c2ccc(OCCCN(CC)CC)cc2)cn1-c1ccc(Oc2ccc(Cl)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3989929
Name AZELIRAGON
Phase Phase III
Structure Type MOL
InChI Key KJNNWYBAOPXVJY-UHFFFAOYSA-N

Known Names

Azeliragon PF-04494700 TTP-488 TTP448 TTP488
2
Targets
5
Activities
2
Assay Types
2
PK Parameters
16
Publications
5
Known Names
4
Indications
1
Mechanisms

Molecular Properties

532.1
MW (Da)
8.44
ALogP
5
HBA
0
HBD
39.5
PSA (Ų)
0.15
QED
2
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -ragon
USAN Year 2016

Extended Properties

Molecular Formula C32H38ClN3O2
MW 532.13
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -1.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Advanced glycosylation end product-specific receptor antagonist ANTAGONIST Advanced glycosylation end product-specific receptor ✓ ✓

Indications

Alzheimer Disease Diabetic Nephropathies Glioblastoma Severe Acute Respiratory Syndrome

Activity Summary

Kd 3 meas. best 7.9
IC50 2 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Advanced glycosylation end product-specific receptor
CHEMBL2176846
 Kd 7.9 7.3667 12.7 3
SUM149PT
CHEMBL4296497
 IC50 5.28 5.28 5292.0 1
Advanced glycosylation end product-specific receptor
CHEMBL2176846
 IC50 4.87 4.87 13470.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 14.9 mL.min-1.g-1 Mus musculus
T1/2 1.553 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Advanced glycosylation end product-specific receptor Kd = 12.7 nM 7.9 Binding affinity to recombinant human RAGE assessed as dissociation constant 35430560
Advanced glycosylation end product-specific receptor Kd = 12.7 nM 7.9 Microscale Thermophoresis Assay: The binding affinity of COMPOUND I and compound... -
Advanced glycosylation end product-specific receptor Kd = 500.0 nM 6.3 Inhibition of amyloid beta (1 to 42) binding to RAGE domain V (unknown origin) b... 28482155
SUM149PT IC50 = 5292.0 nM 5.28 Cytotoxicity against human triple negative SUM149PT cells assessed as cell viabi... 34763082
Advanced glycosylation end product-specific receptor IC50 = 13470.0 nM 4.87 Inhibition of biotinylated human RAGE/amyloid beta interaction incubated for 120... 35430560

Literature References

PubMed DOI Target Context # Activities
35430560 10.1016/j.ejmech.2022.114347 ADMET 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
35430560 10.1016/j.ejmech.2022.114347 SH-SY5Y 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
35430560 10.1016/j.ejmech.2022.114347 Advanced glycosylation end product-specific receptor 2
28482155 10.1021/acs.jmedchem.7b00058 Advanced glycosylation end product-specific receptor 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
34763082 10.1016/j.bmcl.2021.128444 SUM149PT 1
35430560 10.1016/j.ejmech.2022.114347 Sodium-dependent serotonin transporter 1
35430560 10.1016/j.ejmech.2022.114347 Voltage-gated inwardly rectifying potassium channel KCNH2 1
35430560 10.1016/j.ejmech.2022.114347 Cytochrome P450 1A2 1
35430560 10.1016/j.ejmech.2022.114347 Cytochrome P450 2C9 1
35430560 10.1016/j.ejmech.2022.114347 Cytochrome P450 2C19 1
35430560 10.1016/j.ejmech.2022.114347 Cytochrome P450 3A4 1
- 10.6019/EOS300108 HepG2 1

Data from ChEMBL 36 via Core Engine