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Compound Detail

CHEMBL4594250

NETARSUDIL
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(C(=O)OCc2ccc([C@@H](CN)C(=O)Nc3ccc4cnccc4c3)cc2)c(C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4594250
Name NETARSUDIL
Phase Approved
Structure Type MOL
InChI Key OURRXQUGYQRVML-AREMUKBSSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL4753043

Known Names

AR-11324 FREE BASE AR-13324 Netarsudil
3
Targets
34
Activities
2
Assay Types
5
PK Parameters
16
Publications
3
Known Names
5
Indications

Molecular Properties

453.5
MW (Da)
4.89
ALogP
5
HBA
2
HBD
94.3
PSA (Ų)
0.39
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product First in Class Prodrug
USAN Stem -dil
USAN Year 2014

Extended Properties

Molecular Formula C28H27N3O3
MW 453.54
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.93

Indications

Fuchs' Endothelial Dystrophy Fuchs' Endothelial Dystrophy Glaucoma Corneal Edema Glaucoma, Open-Angle

ATC Classification

S01EX05
netarsudil
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 26 meas. best 8.26
Ki 8 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rho-associated protein kinase 2
CHEMBL2973
 Ki 9.0 8.816 1.0 5
Rho-associated protein kinase 1
CHEMBL3231
 Ki 9.0 9.0 1.0 3
Rho-associated protein kinase 1
CHEMBL3231
 IC50 8.26 7.6668 5.5 19
Rho-associated protein kinase 2
CHEMBL2973
 IC50 8.1 7.922 8.0 5
Unchecked
CHEMBL612545
 IC50 7.8 7.45 16.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 2.6 hr Sus scrofa
T1/2 2.917 hr Homo sapiens
T1/2 2.333 hr Oryctolagus cuniculus
T1/2 1.633 hr Canis lupus familiaris
T1/2 1.817 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rho-associated protein kinase 2 Ki = 1.0 nM 9.0 Binding affinity to ROCK2 (unknown origin) assessed as inhibition constant 38852338
Rho-associated protein kinase 1 Ki = 1.0 nM 9.0 Binding affinity to ROCK1 (unknown origin) assessed as inhibition constant 38852338
Rho-associated protein kinase 2 Ki = 1.0 nM 9.0 Inhibition of Rock2 (unknown origin) by Kinase Glo luminescence assay 34536672
Rho-associated protein kinase 1 Ki = 1.0 nM 9.0 Inhibition of Rock1 (unknown origin) by Kinase Glo luminescence assay 34536672
Rho-associated protein kinase 2 Ki = 1.0 nM 9.0 Inhibition of ROCK2 (unknown origin) 33481605
Rho-associated protein kinase 1 Ki = 1.0 nM 9.0 Inhibition of ROCK1 (unknown origin) 33481605
Rho-associated protein kinase 2 Ki = 2.0 nM 8.7 Inhibition of Rock2 (unknown origin) assessed as inhibition constant 34536672
Rho-associated protein kinase 2 Ki = 4.2 nM 8.38 Inhibition of human ROCK2 by Kinase-Glo luminescent assay 32482069
Rho-associated protein kinase 1 IC50 = 5.5 nM 8.26 In Vitro Effect Assay: Table 2: Inhibitory effect of each compound synthesized a... -
Rho-associated protein kinase 2 IC50 = 8.0 nM 8.1 ROCK-II(h) In Vitro Inhibition Activity: Table 2: ROCK-II(h) kinase assays were ... -
Rho-associated protein kinase 2 IC50 = 10.18 nM 7.99 Inhibition of ROCK2 (unknown origin) incubated for 60 mins in presence of ATP by... 39163586
Rho-associated protein kinase 2 IC50 = 11.2 nM 7.95 Inhibition of human ROCK2 using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK as substrate in... 31330446
Rho-associated protein kinase 1 IC50 = 13.18 nM 7.88 Inhibition of ROCK1 (unknown origin) incubated for 10 mins in presence of ATP by... 39163586
Rho-associated protein kinase 1 IC50 = 14.0 nM 7.85 ROCK-I(h) In Vitro Inhibition Activity-Method A: Table 2: ROCK-I(h) kinase assay... -
Rho-associated protein kinase 2 IC50 = 15.0 nM 7.82 ROCK-II(h) In Vitro Inhibition Activity: Table 2: ROCK-II(h) kinase assays were ... -
Rho-associated protein kinase 1 IC50 = 15.0 nM 7.82 ROCK-I(h) In Vitro Inhibition Activity-Method A: Table 2: ROCK-I(h) kinase assay... -
Unchecked IC50 = 16.0 nM 7.8 Induction of disruption of actin stress fibers in human TM1 cells by actin stres... 34536672
Rho-associated protein kinase 1 IC50 = 18.0 nM 7.75 ROCK-I(h) In Vitro Inhibition Activity-Method A: Table 2: ROCK-I(h) kinase assay... -
Rho-associated protein kinase 2 IC50 = 18.0 nM 7.75 ROCK-II(h) In Vitro Inhibition Activity: Table 2: ROCK-II(h) kinase assays were ... -
Rho-associated protein kinase 1 IC50 = 19.0 nM 7.72 ROCK-I(h) In Vitro Inhibition Activity-Method A: Table 2: ROCK-I(h) kinase assay... -

Literature References

PubMed DOI Target Context # Activities
39163586 10.1021/acs.jmedchem.4c01199 ADMET 9
32482069 10.1021/acs.jmedchem.9b01033 ADMET 5
31330446 10.1016/j.ejmech.2019.06.089 MDA-MB-231 2
34536672 10.1016/j.ejmech.2021.113842 Rho-associated protein kinase 2 2
34536672 10.1016/j.ejmech.2021.113842 Unchecked 2
39163586 10.1021/acs.jmedchem.4c01199 Mus musculus 2
31330446 10.1016/j.ejmech.2019.06.089 Rho-associated protein kinase 2 1
31330446 10.1016/j.ejmech.2019.06.089 Rho-associated protein kinase 1 1
32482069 10.1021/acs.jmedchem.9b01033 Rho-associated protein kinase 2 1
33481605 10.1021/acs.jmedchem.0c01511 Rho-associated protein kinase 1 1
33481605 10.1021/acs.jmedchem.0c01511 Rho-associated protein kinase 2 1
34536672 10.1016/j.ejmech.2021.113842 Rho-associated protein kinase 1 1
38852338 10.1016/j.ejmech.2024.116540 Rho-associated protein kinase 1 1
38852338 10.1016/j.ejmech.2024.116540 Rho-associated protein kinase 2 1
39163586 10.1021/acs.jmedchem.4c01199 Rho-associated protein kinase 1 1
39163586 10.1021/acs.jmedchem.4c01199 Rho-associated protein kinase 2 1

Data from ChEMBL 36 via Core Engine