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Compound Detail

CHEMBL531

PERGOLIDE
💊 Approved Drug
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💊 Approved Drug
CCCN1C[C@H](CSC)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21

Basic Information

ChEMBL ID CHEMBL531
Name PERGOLIDE
Phase Approved
Structure Type MOL
InChI Key YEHCICAEULNIGD-MZMPZRCHSA-N
Therapeutic ✓ Yes

Known Names

Pergolida Pergolide
32
Targets
92
Activities
4
Assay Types
3
PK Parameters
20
Publications
2
Known Names
3
Indications

Molecular Properties

314.5
MW (Da)
4.27
ALogP
2
HBA
1
HBD
19.0
PSA (Ų)
0.91
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1988
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Stem -erg-
USAN Year 1979

Extended Properties

Molecular Formula C19H26N2S
MW 314.50
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.61

Indications

Parkinson Disease Cocaine-Related Disorders Substance-Related Disorders

ATC Classification

N04BC02
pergolide
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Drug Warnings

Withdrawn
cardiotoxicity
Valvulopathy
Country: United States; Canada   Year: 2007

Activity Summary

IC50 45 meas. best 8.8
Ki 38 meas. best 9.21
EC50 5 meas. best 9.45
Kd 4 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL217
EC50 9.45 9.45 0.4 1
D(2) dopamine receptor
CHEMBL217
Ki 9.21 7.9871 0.6 7
D(3) dopamine receptor
CHEMBL234
Ki 9.07 8.6525 0.9 4
D(2) dopamine receptor
CHEMBL339
Ki 9.0 9.0 1.0 1
D(2) dopamine receptor
CHEMBL339
IC50 8.8 7.9533 1.6 3
Dopamine receptor
CHEMBL2093868
IC50 8.8 8.306 1.6 5
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 8.74 8.46 1.8 3
D(3) dopamine receptor
CHEMBL3138
IC50 8.62 8.455 2.4 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.41 7.995 3.9 2
D(2) dopamine receptor
CHEMBL339
Kd 8.4 7.6675 4.0 4
Dopamine receptor D2 and D3
CHEMBL2111342
EC50 8.37 8.37 4.3 1
D(3) dopamine receptor
CHEMBL234
IC50 8.27 8.27 5.4 1
Dopamine receptor D2 and D3
CHEMBL2111342
IC50 8.25 8.24 5.6 2
D(4) dopamine receptor
CHEMBL219
Ki 8.21 8.21 6.2 1
D(2) dopamine receptor
CHEMBL339
EC50 8.11 8.11 7.9 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 8.07 8.07 8.5 1
5-hydroxytryptamine receptor 2A
CHEMBL224
EC50 8.05 8.05 8.9 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.85 7.85 14.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 7.82 7.82 15.0 1
Dopamine receptor
CHEMBL2096970
IC50 7.75 7.295 18.0 2
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.75 7.75 18.0 1
Unchecked
CHEMBL612545
IC50 7.75 6.23 18.0 6
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 7.54 7.54 29.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.41 7.41 39.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 7.4 7.4 40.0 1
Cerebral cortex alpha adrenergic receptor
CHEMBL2111420
IC50 7.39 7.39 41.0 1
Adrenergic receptor alpha-2
CHEMBL2093864
IC50 7.39 7.08 41.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.33 7.165 47.0 2
D(2) dopamine receptor
CHEMBL3998
IC50 7.32 7.32 48.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.31 7.31 49.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 7.19 7.19 64.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 7.12 7.12 76.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 7.06 7.06 87.0 1
D(2) dopamine receptor
CHEMBL217
IC50 6.96 6.96 111.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.92 6.92 120.2 1
Serotonin (5-HT) receptor
CHEMBL2094123
IC50 6.85 6.635 140.0 2
Cytochrome P450 2D6
CHEMBL289
IC50 6.7 6.7 200.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.7 6.7 199.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.69 6.69 205.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
EC50 6.66 6.66 218.8 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.58 6.58 264.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.47 6.0333 339.0 3
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.42 6.42 379.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 6.26 6.26 550.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.17 6.17 679.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.13 6.13 744.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.11 6.11 781.0 1
Unchecked
CHEMBL612545
Ki 6.05 5.7675 887.0 4
Alpha-1A adrenergic receptor
CHEMBL229
Ki 6.05 6.05 888.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.85 5.85 1410.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 55.0 % Mus musculus
Fu 0.027 - Rattus norvegicus
T1/2 2.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor EC50 = 0.3548 nM 9.45 Agonist activity at dopamine D2 receptor short isoform (unknown origin) expresse... -
D(2) dopamine receptor Ki = 0.62 nM 9.21 Binding affinity to dopamine D2 receptor (unknown origin) assessed as inhibition... 38516587
D(3) dopamine receptor Ki = 0.8511 nM 9.07 Inhibition constant against [3H]-spiperone binding to human Dopamine receptor D3... 15801839
D(2) dopamine receptor Ki = 1.0 nM 9.0 Compound was tested for antagonistic activity against D2 receptor from rat stria... 8496900
D(2) dopamine receptor IC50 = 1.6 nM 8.8 Inhibitory activity against Dopamine receptor D2 in rat corpus striatum using [3... 2571732
Dopamine receptor IC50 = 1.6 nM 8.8 Inhibition of [3H]apomorphine binding to dopamine receptor of rat corpus striatu... 6876078
5-hydroxytryptamine receptor 1A Ki = 1.8 nM 8.74 Binding affinity against 5-hydroxytryptamine 1A receptor from bovine hippocampus... 8496900
D(3) dopamine receptor Ki = 1.832 nM 8.74 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(3) dopamine receptor IC50 = 2.41 nM 8.62 Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D... -
Dopamine receptor IC50 = 3.1 nM 8.51 In vitro affinity for dopamine receptor by displacement of [3H]- apomorphine in ... 6298427
Dopamine receptor IC50 = 3.1 nM 8.51 Dopaminergic activity assessed in vitro for displacement of [3H]apomorphine from... 6094811
5-hydroxytryptamine receptor 2A Ki = 3.904 nM 8.41 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
D(2) dopamine receptor Ki = 4.0 nM 8.4 Binding affinity to D2 receptor (unknown origin) assessed as inhibition constant 39038276
D(2) dopamine receptor Ki = 4.0 nM 8.4 Binding affinity towards Dopamine receptor D2 by displacement of [3H]U-86170. 9057850
D(3) dopamine receptor Ki = 4.0 nM 8.4 Binding affinity to D3 receptor (unknown origin) assessed as inhibition constant 39038276
D(2) dopamine receptor Kd = 4.0 nM 8.4 In vitro affinity at mutant D2 receptor (S194A) in C6 (glioma) cell membranes. 10956209
D(3) dopamine receptor Ki = 4.0 nM 8.4 Binding affinity towards Dopamine receptor D3 by displacement of [3H](+)-7-OH-DP... 9057850
5-hydroxytryptamine receptor 1A Ki = 4.0 nM 8.4 Binding affinity towards Serotonin 5-hydroxytryptamine 1A receptor by displaceme... 9057850
Dopamine receptor IC50 = 4.1 nM 8.39 Inhibition of [3H]dopamine binding to dopamine receptor of rat corpus striatum 6876078
Dopamine receptor D2 and D3 EC50 = 4.31 nM 8.37 Agonist activity at Rattus norvegicus (rat) dopamine D2/D3 receptor transfected ... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 346
- 10.5281/zenodo.13943903 ADMET 89
16472241 10.2174/1570163043334794 Hepatotoxicity 18
6115056 10.1021/jm00135a002 Felis catus 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
3102743 10.1021/jm00386a023 Rattus norvegicus 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2571732 10.1021/jm00130a027 Rattus norvegicus 6
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
10956209 10.1021/jm990526y D(2) dopamine receptor 4
- 10.1007/s00044-004-0006-x Dopamine receptor D2 and D3 4
- 10.1007/s00044-004-0006-x D(2) dopamine receptor 4
7190615 10.1021/jm00181a021 Rattus norvegicus 4
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 3
3973904 10.1021/jm00381a017 Rattus norvegicus 3
3712381 10.1021/jm00156a007 Dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
6876078 10.1021/jm00362a005 Dopamine receptor 3
24878269 10.1021/jm5003759 D(2) dopamine receptor 3

Data from ChEMBL 36 via Core Engine