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Compound Detail

CHEMBL589

ROPINIROLE
💊 Approved Drug
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💊 Approved Drug
CCCN(CCC)CCc1cccc2c1CC(=O)N2

Basic Information

ChEMBL ID CHEMBL589
Name ROPINIROLE
Phase Approved
Structure Type MOL
InChI Key UHSKFQJFRQCDBE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

NSC-758917 Ropinirol Ropinirole Ropitor SK&F 101468 SK&F-101468
13
Targets
42
Activities
3
Assay Types
1
PK Parameters
20
Publications
6
Known Names
7
Indications

Molecular Properties

260.4
MW (Da)
2.85
ALogP
2
HBA
1
HBD
32.3
PSA (Ų)
0.82
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1993

Extended Properties

Molecular Formula C16H24N2O
MW 260.38
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.47

Indications

Parkinson Disease Restless Legs Syndrome Cocaine-Related Disorders Fibromyalgia Stroke Unverricht-Lundborg Syndrome Hyperprolactinemia

ATC Classification

N04BC04
ropinirole
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Activity Summary

EC50 22 meas. best 8.41
Ki 15 meas. best 8.54
IC50 5 meas. best 7.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
Ki 8.54 7.7275 2.9 4
D(2) dopamine receptor
CHEMBL217
Ki 8.43 7.5767 3.7 3
Dopamine receptor D2 and D3
CHEMBL2111342
EC50 8.41 8.41 3.9 1
D(3) dopamine receptor
CHEMBL234
EC50 8.4 8.025 4.0 4
D(2) dopamine receptor
CHEMBL217
EC50 8.19 6.8708 6.5 12
D(4) dopamine receptor
CHEMBL219
Ki 8.11 8.11 7.8 1
D(3) dopamine receptor
CHEMBL3138
Ki 7.53 7.53 29.3 2
Dopamine receptor D2 and D3
CHEMBL2111342
IC50 7.25 6.63 56.1 2
D(2) dopamine receptor
CHEMBL339
EC50 7.12 7.12 75.5 1
Oryctolagus cuniculus
CHEMBL374
EC50 7.0 7.0 100.0 2
Dopamine receptor
CHEMBL2096905
EC50 7.0 7.0 100.0 1
D(3) dopamine receptor
CHEMBL3138
IC50 6.97 6.97 107.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
EC50 6.85 6.85 141.2 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 5.77 5.77 1706.0 1
D(2) dopamine receptor
CHEMBL339
IC50 5.74 5.74 1803.0 1
D(2) dopamine receptor
CHEMBL339
Ki 5.57 5.57 2674.0 2
D(2) dopamine receptor
CHEMBL3998
IC50 5.17 5.17 6810.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 4.49 4.49 32500.0 1
D(1B) dopamine receptor
CHEMBL1850
Ki 4.38 4.38 41211.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 55.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor Ki = 2.9 nM 8.54 Binding affinity to human dopamine D3 receptor -
D(2) dopamine receptor Ki = 3.7 nM 8.43 Binding affinity to human dopamine D2 receptor -
Dopamine receptor D2 and D3 EC50 = 3.89 nM 8.41 Agonist activity at Rattus norvegicus (rat) dopamine D2/D3 receptor transfected ... -
D(3) dopamine receptor EC50 = 4.0 nM 8.4 Agonist activity at human recombinant dopamine D3 receptor expressed in CHO cell... 17976986
D(2) dopamine receptor EC50 = 6.457 nM 8.19 Agonist activity at dopamine D2 receptor short isoform (unknown origin) expresse... -
D(2) dopamine receptor Ki = 7.2 nM 8.14 Binding affinity towards Dopamine receptor D2 by displacement of [3H]U-86170. 9057850
D(4) dopamine receptor Ki = 7.8 nM 8.11 Binding affinity to human dopamine D4 receptor -
D(3) dopamine receptor EC50 = 10.3 nM 7.99 Agonist activity at human dopamine D3 receptor expressed in CHO cells assessed a... 20605099
D(3) dopamine receptor EC50 = 10.3 nM 7.99 Agonist activity at human dopamine D3 receptor expressed in CHO cells by [35S]GT... 20146482
D(3) dopamine receptor Ki = 19.0 nM 7.72 Binding affinity towards Dopamine receptor D3 by displacement of [3H](+)-7-OH-DP... 9057850
D(3) dopamine receptor EC50 = 19.2 nM 7.72 Agonist activity at human dopamine D3 receptor expressed in mouse AtT-20 cells a... 20038106
D(3) dopamine receptor Ki = 29.3 nM 7.53 Displacement of [3H]spiperone from rat cloned dopamine D3 receptor expressed in ... 23623679
D(3) dopamine receptor Ki = 29.3 nM 7.53 Displacement of [3H]spiperone from rat D3 receptor expressed in HEK293 cells 20605099
D(2) dopamine receptor EC50 = 30.0 nM 7.52 Partial agonist activity at human D2SR expressed in HEK293T cells co-expressing ... 28489379
D(3) dopamine receptor Ki = 36.31 nM 7.44 Displacement of [3H]spiperone form human cloned dopamine D3 receptor expressed i... 19324548
Dopamine receptor D2 and D3 IC50 = 56.1 nM 7.25 Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D... -
D(3) dopamine receptor Ki = 61.0 nM 7.21 Agonist activity at dopamine D3 receptor (unknown origin) 24012118
D(2) dopamine receptor EC50 = 75.5 nM 7.12 Agonist activity at Rattus norvegicus (rat) dopamine D2 receptor transfected in ... -
D(2) dopamine receptor EC50 = 83.0 nM 7.08 Agonist activity at human recombinant dopamine D2 receptor expressed in rat pitu... 17976986
D(2) dopamine receptor EC50 = 89.0 nM 7.05 Partial agonist activity at human D2SR expressed in HEK293T cells co-expressing ... 28489379

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 63
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
28489379 10.1021/acs.jmedchem.7b00363 D(2) dopamine receptor 6
28870802 10.1016/j.bmc.2017.08.037 D(2) dopamine receptor 5
- 10.1007/s00044-004-0006-x Dopamine receptor D2 and D3 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
20605099 10.1016/j.bmc.2010.06.025 D(2) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
20038106 10.1021/jm901184n Rattus norvegicus 3
20605099 10.1016/j.bmc.2010.06.025 D(3) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 3
- 10.1007/s00044-004-0006-x D(2) dopamine receptor 3

Data from ChEMBL 36 via Core Engine