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Compound Detail

CHEMBL3426621

RIPASUDIL
🧪 Phase III
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🧪 Phase III
C[C@H]1CNCCCN1S(=O)(=O)c1cccc2cncc(F)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3426621
Name RIPASUDIL
Phase Phase III
Structure Type MOL
InChI Key QSKQVZWVLOIIEV-NSHDSACASA-N

Known Names

Ripasudil
18
Targets
36
Activities
4
Assay Types
0
PK Parameters
20
Publications
1
Known Names
5
Indications
1
Mechanisms

Molecular Properties

323.4
MW (Da)
1.75
ALogP
4
HBA
1
HBD
62.3
PSA (Ų)
0.91
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -dil

Extended Properties

Molecular Formula C15H18FN3O2S
MW 323.39
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -1.09

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Rho-associated protein kinase inhibitor INHIBITOR Rho-associated protein kinase ✓ ✓

Indications

Corneal Edema Fuchs' Endothelial Dystrophy Fuchs' Endothelial Dystrophy Glaucoma Retinopathy of Prematurity

ATC Classification

S01EX07
ripasudil
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Kd 18 meas. best 7.48
IC50 16 meas. best 8.42
EC50 1 meas. best 6.68
Ki 1 meas. best 6.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rho-associated protein kinase 2
CHEMBL2973
 IC50 8.42 7.7011 3.8 9
Rho-associated protein kinase 1
CHEMBL3231
 IC50 7.76 7.3586 17.4 7
Rho-associated protein kinase 1
CHEMBL3231
 Kd 7.48 7.48 33.0 1
Rho-associated protein kinase 2
CHEMBL2973
 Kd 7.08 7.08 83.0 1
Unchecked
CHEMBL612545
 EC50 6.68 6.68 210.0 1
Serine/threonine-protein kinase N2
CHEMBL3032
 Kd 6.54 6.54 285.0 1
Rho-associated protein kinase 2
CHEMBL2973
 Ki 6.48 6.48 330.0 1
Serine/threonine-protein kinase N1
CHEMBL3384
 Kd 6.38 6.38 416.0 1
Unchecked
CHEMBL612545
 Kd 6.24 6.24 571.0 1
Aurora kinase B
CHEMBL2185
 Kd 5.94 5.94 1152.0 1
5'-AMP-activated protein kinase subunit gamma-1
CHEMBL2393
 Kd 5.74 5.74 1807.0 1
Protein kinase C delta type
CHEMBL2996
 Kd 5.61 5.61 2470.0 1
Dual specificity mitogen-activated protein kinase kinase 3
CHEMBL2109
 Kd 5.51 5.51 3079.0 1
5'-AMP-activated protein kinase catalytic subunit alpha-1
CHEMBL4045
 Kd 5.49 5.49 3269.0 1
Mitogen-activated protein kinase kinase kinase kinase 3
CHEMBL5432
 Kd 5.49 5.49 3219.0 1
Ribosyldihydronicotinamide dehydrogenase [quinone]
CHEMBL3959
 Kd 5.43 5.43 3699.0 1
Serine/threonine-protein kinase D2
CHEMBL4900
 Kd 5.43 5.43 3703.0 1
Serine/threonine-protein kinase MARK2
CHEMBL3831
 Kd 5.22 5.22 6017.0 1
Serine/threonine-protein kinase PLK4
CHEMBL3788
 Kd 5.09 5.09 8141.0 1
Serine/threonine-protein kinase TAO3
CHEMBL5701
 Kd 4.93 4.93 11799.0 1
Cyclin-dependent kinase 9
CHEMBL3116
 Kd 4.88 4.88 13279.0 1
MAP/microtubule affinity-regulating kinase 3
CHEMBL5600
 Kd 4.24 4.24 58240.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rho-associated protein kinase 2 IC50 = 3.8 nM 8.42 Inhibition of human N-terminal GST-tagged ROCK2 expressed in baculovirus-infecte... 25898023
Rho-associated protein kinase 2 IC50 = 13.1 nM 7.88 Inhibition of ROCK2 (unknown origin) incubated for 60 mins in presence of ATP by... 39163586
Rho-associated protein kinase 1 IC50 = 17.4 nM 7.76 Inhibition of ROCK1 (unknown origin) incubated for 10 mins in presence of ATP by... 39163586
Rho-associated protein kinase 2 IC50 = 19.0 nM 7.72 Inhibition of Rock2 (unknown origin) 34536672
Rho-associated protein kinase 2 IC50 = 19.0 nM 7.72 Inhibition of ROCK2 (unknown origin) 33481605
Rho-associated protein kinase 2 IC50 = 19.0 nM 7.72 Inhibition of N-terminal GST-fused human ROCK2 catalytic domain ( 1 to 553 resid... 32482069
Rho-associated protein kinase 2 IC50 = 19.0 nM 7.72 Inhibition of ROCK2 (unknown origin) 32324396
Rho-associated protein kinase 2 IC50 = 19.0 nM 7.72 Inhibition of ROCK2 (unknown origin) 26356532
Rho-associated protein kinase 2 IC50 = 20.0 nM 7.7 Inhibition of ROCK2 (unknown origin) 32805407
Rho-associated protein kinase 1 Kd = 33.0 nM 7.48 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
Rho-associated protein kinase 1 IC50 = 50.0 nM 7.3 Inhibition of ROCK1 (unknown origin) 32805407
Rho-associated protein kinase 1 IC50 = 51.0 nM 7.29 Inhibition of ROCK1 (unknown origin) 26356532
Rho-associated protein kinase 1 IC50 = 51.0 nM 7.29 Inhibition of ROCK1 (unknown origin) 32324396
Rho-associated protein kinase 1 IC50 = 51.0 nM 7.29 Inhibition of N-terminal GST-fused human ROCK1 catalytic domain ( 1 to 477 resid... 32482069
Rho-associated protein kinase 1 IC50 = 51.0 nM 7.29 Inhibition of ROCK1 (unknown origin) 33481605
Rho-associated protein kinase 1 IC50 = 51.0 nM 7.29 Inhibition of Rock1 (unknown origin) 34536672
Rho-associated protein kinase 2 Kd = 83.0 nM 7.08 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
Rho-associated protein kinase 2 IC50 = 197.0 nM 6.71 Inhibition of human N-terminal GST-tagged ROCK2 expressed in baculovirus-infecte... 25898023
Unchecked EC50 = 210.0 nM 6.68 Inhibition of ROCK-catalysed MLC Thr18/Ser19 phosphorylation in rat A7r5 cells a... 25898023
Serine/threonine-protein kinase N2 Kd = 285.0 nM 6.54 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878

Literature References

PubMed DOI Target Context # Activities
32482069 10.1021/acs.jmedchem.9b01033 Unchecked 10
29191878 10.1126/science.aan4368 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
26486225 10.1021/acs.jmedchem.5b00683 Mus musculus 3
25898023 10.1021/acs.jmedchem.5b00308 Rho-associated protein kinase 2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
33481605 10.1021/acs.jmedchem.0c01511 Rho-associated protein kinase 2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
29191878 10.1126/science.aan4368 Acyl-CoA dehydrogenase family member 10 1
29191878 10.1126/science.aan4368 Acyl-CoA dehydrogenase family member 11 1
29191878 10.1126/science.aan4368 Peroxisomal acyl-coenzyme A oxidase 1 1
29191878 10.1126/science.aan4368 Peroxisomal acyl-coenzyme A oxidase 3 1
29191878 10.1126/science.aan4368 Actin-related protein 2 1
29191878 10.1126/science.aan4368 Actin-related protein 3 1
39163586 10.1021/acs.jmedchem.4c01199 Rho-associated protein kinase 2 1
29191878 10.1126/science.aan4368 Tyrosine-protein kinase ABL1 1
29191878 10.1126/science.aan4368 AP2-associated protein kinase 1 1
29191878 10.1126/science.aan4368 AarF domain-containing protein kinase 1 1
29191878 10.1126/science.aan4368 Atypical kinase COQ8A, mitochondrial 1
26356532 10.1021/acs.jmedchem.5b00828 Rho-associated protein kinase 1 1

Data from ChEMBL 36 via Core Engine