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Compound Detail

CHEMBL206815

APRATASTAT
🧪 Phase II
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🧪 Phase II
CC1(C)SCCN(S(=O)(=O)c2ccc(OCC#CCO)cc2)[C@H]1C(=O)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL206815
Name APRATASTAT
Phase Phase II
Structure Type MOL
InChI Key MAVDNGWEBZTACC-HNNXBMFYSA-N

Known Names

Apratastat TMI-005 TMI-05
7
Targets
22
Activities
1
Assay Types
3
PK Parameters
10
Publications
3
Known Names
1
Indications
2
Mechanisms

Molecular Properties

414.5
MW (Da)
0.45
ALogP
7
HBA
3
HBD
116.2
PSA (Ų)
0.36
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -stat
USAN Year 2000

Extended Properties

Molecular Formula C17H22N2O6S2
MW 414.51
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness -0.73

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Matrix metalloproteinase 13 inhibitor INHIBITOR Collagenase 3 ✓ ✓
ADAM17 inhibitor INHIBITOR Disintegrin and metalloproteinase domain-containing protein 17 ✓ ✓

Indications

Arthritis, Rheumatoid

Activity Summary

IC50 22 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 8.4 7.3922 4.0 9
Collagenase 3
CHEMBL280
 IC50 8.1 8.1 8.0 1
Stromelysin-1
CHEMBL283
 IC50 8.0 8.0 10.0 2
Interstitial collagenase
CHEMBL332
 IC50 7.48 7.0533 33.0 3
Disintegrin and metalloproteinase domain-containing protein 10
CHEMBL5028
 IC50 7.15 7.15 71.0 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 7.09 7.09 82.0 2
Disintegrin and metalloproteinase domain-containing protein 9
CHEMBL5982
 IC50 7.07 7.07 85.0 2

Pharmacokinetic Data

Parameter Value Units Species
F 24.0 % Mus musculus
F 8.0 % Rattus norvegicus
F 36.0 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 4.0 nM 8.4 Inhibition of recombinant human TACE catalytic domain using Mca-Pro-Leu-Ala-Gln-... 28274635
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 5.0 nM 8.3 TACE Enzyme Assay: The TACE enzyme is an internal production (carried out accord... -
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 5.0 nM 8.3 Inhibition Assay: The TACE enzyme is an internal production (carried out accordi... -
Collagenase 3 IC50 = 8.0 nM 8.1 Inhibition of MMP13 16426848
Stromelysin-1 IC50 = 10.0 nM 8.0 Inhibition Assay: The molecules are tested in dose-response studies on the follo... -
Stromelysin-1 IC50 = 10.0 nM 8.0 Inhibition Assay: The molecules are dose-response tested on the following enzyme... -
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 20.0 nM 7.7 Inhibition of TACE 16426848
Interstitial collagenase IC50 = 33.0 nM 7.48 Inhibition of MMP1 16426848
Disintegrin and metalloproteinase domain-containing protein 10 IC50 = 71.0 nM 7.15 Inhibition Assay: The molecules are tested in dose-response studies on the follo... -
Disintegrin and metalloproteinase domain-containing protein 10 IC50 = 71.0 nM 7.15 Inhibition Assay: The molecules are dose-response tested on the following enzyme... -
Matrix metalloproteinase-9 IC50 = 82.0 nM 7.09 Inhibition Assay: The molecules are tested in dose-response studies on the follo... -
Matrix metalloproteinase-9 IC50 = 82.0 nM 7.09 Inhibition Assay: The molecules are dose-response tested on the following enzyme... -
Disintegrin and metalloproteinase domain-containing protein 9 IC50 = 85.0 nM 7.07 Inhibition Assay: The molecules are tested in dose-response studies on the follo... -
Disintegrin and metalloproteinase domain-containing protein 9 IC50 = 85.0 nM 7.07 Inhibition Assay: The molecules are dose-response tested on the following enzyme... -
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 120.0 nM 6.92 Inhibition of TACE in NHEK assessed as reduction in LPS/TPA-stimulated TNFalpha ... 28274635
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 125.89 nM 6.9 Inhibition of TACE in NHEK assessed as reduction in LPS/TPA-stimulated TNFalpha ... 28274635
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 140.0 nM 6.85 Inhibition of LPS-stimulated TNF production in THP cells at 1 uM 16426848
Interstitial collagenase IC50 = 145.0 nM 6.84 Inhibition Assay: The molecules are tested in dose-response studies on the follo... -
Interstitial collagenase IC50 = 145.0 nM 6.84 Inhibition Assay: The molecules are dose-response tested on the following enzyme... -
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 158.49 nM 6.8 Inhibition of TACE in human PBMC assessed as inhibition of TNFalpha production 28274635

Literature References

PubMed DOI Target Context # Activities
16426848 10.1016/j.bmcl.2005.12.020 Disintegrin and metalloproteinase domain-containing protein 17 5
28274635 10.1016/j.bmcl.2017.02.035 Disintegrin and metalloproteinase domain-containing protein 17 4
16426848 10.1016/j.bmcl.2005.12.020 Mus musculus 3
16426848 10.1016/j.bmcl.2005.12.020 Interstitial collagenase 1
16426848 10.1016/j.bmcl.2005.12.020 Collagenase 3 1
16426848 10.1016/j.bmcl.2005.12.020 Caco-2 1
16426848 10.1016/j.bmcl.2005.12.020 Rattus norvegicus 1
16426848 10.1016/j.bmcl.2005.12.020 Canis familiaris 1
19095454 10.1016/j.bmc.2008.11.067 Disintegrin and metalloproteinase domain-containing protein 17 1
28274635 10.1016/j.bmcl.2017.02.035 No relevant target 1

Data from ChEMBL 36 via Core Engine