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Compound Detail

CHEMBL3828074

ZIRITAXESTAT
🧪 Phase III
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🧪 Phase III
CCc1nc2c(C)cc(N3CCN(CC(=O)N4CC(O)C4)CC3)cn2c1N(C)c1nc(-c2ccc(F)cc2)c(C#N)s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3828074
Name ZIRITAXESTAT
Phase Phase III
Structure Type MOL
InChI Key REQQVBGILUTQNN-UHFFFAOYSA-N

Known Names

G-451990 G451990 GLPG-1690 Glpg1690 Ziritaxestat Ziritaxestatn
7
Targets
32
Activities
2
Assay Types
21
PK Parameters
20
Publications
6
Known Names
3
Indications
1
Mechanisms

Molecular Properties

588.7
MW (Da)
3.43
ALogP
10
HBA
1
HBD
104.2
PSA (Ų)
0.35
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -stat
USAN Year 2020

Extended Properties

Molecular Formula C30H33FN8O2S
MW 588.71
Aromatic Rings 4
Heavy Atoms 42
NP-Likeness -1.63

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Autotaxin inhibitor INHIBITOR Autotaxin ✓ ✓

Indications

Idiopathic Pulmonary Fibrosis Scleroderma, Systemic Fibrosis

Activity Summary

IC50 31 meas. best 11.0
Ki 1 meas. best 7.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Autotaxin
CHEMBL3691
 IC50 11.0 7.6285 0.0 20
Unchecked
CHEMBL612545
 IC50 8.3 7.455 5.0 2
Autotaxin
CHEMBL3691
 Ki 7.82 7.82 15.0 1
Autotaxin
CHEMBL3826870
 IC50 6.88 6.575 131.0 2
Autotaxin
CHEMBL3826871
 IC50 6.65 6.515 224.0 2
MDA-MB-231
CHEMBL400
 IC50 5.2 5.2 6270.0 1
MCF7
CHEMBL387
 IC50 5.08 5.08 8320.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.82 4.82 15000.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 5553.0 ng.hr.mL-1 Mus musculus
AUC 20786.0 ng.hr.mL-1 Mus musculus
AUC 101225.0 ng.hr.mL-1 Mus musculus
CL 3.833 mL.min-1.kg-1 Mus musculus
CL 11.5 mL.min-1.kg-1 Rattus norvegicus
CL 2.0 mL.min-1.kg-1 Canis lupus familiaris
CL 11.5 mL.min-1.kg-1 Rattus norvegicus
Cmax 1826.03 nM Mus musculus
Cmax 7411.12 nM Mus musculus
Cmax 36299.71 nM Mus musculus
F 29.0 % Mus musculus
F 37.0 % Rattus norvegicus
F 63.0 % Canis lupus familiaris
F 34.0 % Rattus norvegicus
T1/2 5.0 hr Homo sapiens
T1/2 2.21 hr Mus musculus
T1/2 2.22 hr Mus musculus
T1/2 3.79 hr Mus musculus
Tmax 3.0 hr Mus musculus
Tmax 1.0 hr Mus musculus
Tmax 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Autotaxin IC50 = 0.01 nM 11.0 Inhibition of human ATX using FS3 as substrate preincubated for 30 mins followed... 26745766
Autotaxin IC50 = 1.3 nM 8.89 Inhibition of human ATX pre-incubated for 45 mins before fluorogenic substrate-3... 32479084
Autotaxin IC50 = 2.9 nM 8.54 Inhibition of human ATX using FS-3 as substrate preincubated for 45 mins followe... 34428714
Autotaxin IC50 = 2.9 nM 8.54 Inhibition of human ATX using FS-3 as substrate preincubated for 45 mins followe... 34742015
Autotaxin IC50 = 3.1 nM 8.51 Inhibition of glycosylated human ATX using FS-3 as substrate preincubated for 45... 33032188
Autotaxin IC50 = 3.7 nM 8.43 Inhibition of human C-terminal His6-tagged ATX beta expressed in Sf9 insect cell... 32535330
Autotaxin IC50 = 3.9 nM 8.41 Negative allosteric modulation activity against human ATX using FS-3 as substrat... 35436669
Autotaxin IC50 = 5.0 nM 8.3 Biochemical ATX Assay (Assay A): 5 nM recombinant ATX (Cayman Chemicals) was sup... -
Unchecked IC50 = 5.0 nM 8.3 Biochemical ATX Assa: 5 nM recombinant ATX (Cayman Chemicals) was supplemented t... -
Autotaxin Ki = 15.0 nM 7.82 Competitive inhibition of human ATX using LPC (16:0) as substrate after 30 mins ... 28414242
Autotaxin IC50 = 50.0 nM 7.3 Biochemical Assay: TABLE VI: (UniProtKB/SwissProt Sequence ref Q13822) biochemic... -
Autotaxin IC50 = 73.4 nM 7.13 Inhibition of human ATX in using LPC as substrate by fluorescence based micropla... 38091892
Autotaxin IC50 = 100.0 nM 7.0 Inhibition of ATX in human plasma assessed as inhibition of LPA production after... 26745766
Autotaxin IC50 = 100.0 nM 7.0 Inhibition of ATX (unknown origin) 28112925
Autotaxin IC50 = 131.0 nM 6.88 Inhibition of human ATX using LPC (16:0) as substrate after 30 mins by horseradi... 28414242
Autotaxin IC50 = 131.0 nM 6.88 Inhibition of rat ATX lysoPLD activity using LPC as substrate assessed as reduct... 35440138
Autotaxin IC50 = 131.0 nM 6.88 Inhibition of human ATX by LPC choline release assay 32479084
Autotaxin IC50 = 131.0 nM 6.88 Inhibition of recombinant human ATX using lysophosphatidylcholine as substrate b... 26745766
Autotaxin IC50 = 200.0 nM 6.7 Inhibition of human ATX using LPC as substrate preincubated with compound for 15... 36702053
Autotaxin IC50 = 224.0 nM 6.65 Inhibition of recombinant mouse ATX using lysophosphatidylcholine as substrate b... 26745766

Literature References

PubMed DOI Target Context # Activities
28414242 10.1021/acs.jmedchem.7b00032 Mus musculus 33
26745766 10.1021/acs.jmedchem.5b01599 Autotaxin 8
28414242 10.1021/acs.jmedchem.7b00032 Autotaxin 8
28414242 10.1021/acs.jmedchem.7b00032 Plasma 7
34742015 10.1016/j.ejmech.2021.113951 Mus musculus 5
32479084 10.1021/acs.jmedchem.0c00506 Mus musculus 5
34742015 10.1016/j.ejmech.2021.113951 Unchecked 4
36702053 10.1016/j.ejmech.2023.115130 No relevant target 3
34428714 10.1016/j.bmc.2021.116362 Mus musculus 2
32479084 10.1021/acs.jmedchem.0c00506 Autotaxin 2
32584034 10.1021/acs.jmedchem.0c00688 Mus musculus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37683364 10.1016/j.ejmech.2023.115762 ADMET 2
36702053 10.1016/j.ejmech.2023.115130 Autotaxin 2
28414242 10.1021/acs.jmedchem.7b00032 Voltage-gated inwardly rectifying potassium channel KCNH2 2
28414242 10.1021/acs.jmedchem.7b00032 Canis familiaris 2
28414242 10.1021/acs.jmedchem.7b00032 Rattus norvegicus 2
32535330 10.1016/j.ejmech.2020.112456 MCF7 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
28112925 10.1021/acs.jmedchem.6b01270 Autotaxin 1

Data from ChEMBL 36 via Core Engine