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Compound Detail

CHEMBL493

BROMOCRIPTINE
💊 Approved Drug
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💊 Approved Drug
CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4c5cccc6[nH]c(Br)c(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12

Basic Information

ChEMBL ID CHEMBL493
Name BROMOCRIPTINE
Phase Approved
Structure Type MOL
InChI Key OZVBMTJYIDMWIL-AYFBDAFISA-N
Therapeutic ✓ Yes

Known Names

2-bromo-.alpha.-ergocryptine Bromergocryptine Bromocriptina Bromocriptine CB-154 Ergocryptine, 2-bromo- Parlodel SANDOZ 15-754
36
Targets
80
Activities
4
Assay Types
13
PK Parameters
20
Publications
8
Known Names
9
Indications

Molecular Properties

654.6
MW (Da)
3.19
ALogP
6
HBA
3
HBD
118.2
PSA (Ų)
0.46
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1978
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1976

Extended Properties

Molecular Formula C32H40BrN5O5
MW 654.61
Aromatic Rings 2
Heavy Atoms 43
NP-Likeness 1.29

Indications

Parkinson Disease Peripartum Cardiomyopathy Diabetes Mellitus, Type 1 Intellectual Disability Obesity Ovarian Hyperstimulation Syndrome Adenomyosis Alzheimer Disease Anorexia Nervosa

ATC Classification

G02CB01
bromocriptine
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: OTHER GYNECOLOGICALS
N04BC01
bromocriptine
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Activity Summary

Ki 37 meas. best 9.7
IC50 28 meas. best 9.22
EC50 11 meas. best 9.3
Kd 4 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
Ki 9.7 7.94 0.2 3
D(2) dopamine receptor
CHEMBL217
EC50 9.3 9.3 0.5 1
D(2) dopamine receptor
CHEMBL217
Ki 9.28 8.3567 0.5 6
D(3) dopamine receptor
CHEMBL234
IC50 9.22 9.22 0.6 1
D(2) dopamine receptor
CHEMBL217
IC50 8.8 8.8 1.6 1
5-hydroxytryptamine receptor 2A
CHEMBL224
EC50 8.75 8.75 1.8 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 8.71 8.71 2.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 8.55 8.55 2.8 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 8.49 8.49 3.2 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 8.45 8.45 3.5 1
D(2) dopamine receptor
CHEMBL339
Kd 8.4 8.0925 4.0 4
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.28 8.28 5.3 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 8.26 7.92 5.5 2
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 8.25 8.25 5.6 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 8.16 8.16 7.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 8.08 8.08 8.3 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.0 7.46 10.0 2
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 8.0 8.0 10.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.82 7.82 15.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 7.82 7.82 15.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 7.8 7.8 16.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 7.75 7.75 18.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.66 7.66 22.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 7.62 7.62 24.0 2
Dopamine receptor
CHEMBL2093868
IC50 7.55 7.55 27.9 2
Alpha-1D adrenergic receptor
CHEMBL223
IC50 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
Ki 7.46 6.335 35.0 2
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 7.46 7.46 35.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.44 7.44 36.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 7.33 7.33 47.0 1
Unchecked
CHEMBL612545
IC50 7.28 6.225 53.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.12 7.12 76.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 6.99 6.99 103.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.56 6.56 278.0 1
D(4) dopamine receptor
CHEMBL219
Ki 6.43 6.43 373.0 1
Cerebral cortex alpha adrenergic receptor
CHEMBL2111420
IC50 6.29 6.29 514.0 1
Adrenergic receptor alpha-2
CHEMBL2093864
IC50 6.29 6.29 514.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.28 6.28 520.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.27 6.27 532.0 1
dengue virus type 4
CHEMBL613728
EC50 6.1 6.1 800.0 1
dengue virus type 2
CHEMBL613966
EC50 6.1 6.1 800.0 1
dengue virus type 3
CHEMBL612717
EC50 6.1 6.1 800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.92 5.76 1200.0 2
Beta-1 adrenergic receptor
CHEMBL213
Ki 5.86 5.86 1386.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 5.84 5.655 1444.0 2
Androgen receptor
CHEMBL3072
Ki 5.82 5.82 1521.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
EC50 5.8 5.8 1584.9 1
dengue virus type 1
CHEMBL613360
EC50 5.8 5.8 1600.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.7 5.61 2000.0 2
Androgen receptor
CHEMBL3072
IC50 5.64 5.64 2281.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2.377 ng.hr.mL-1 Mus musculus
Cmax 0.711 nM Homo sapiens
Cmax 0.000628 ug.mL-1 Homo sapiens
F 4.5 % Homo sapiens
F 90.0 % Mus musculus
Fu 0.002 - Homo sapiens
Fu 0.002 - Macaca fascicularis
Fu 0.002 - Canis lupus familiaris
Fu 0.002 - Cavia porcellus
Fu 0.002 - Mus musculus
Fu 0.001 - Rattus norvegicus
Fu 0.002 - Rattus norvegicus
T1/2 4.85 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor Ki = 0.202 nM 9.7 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor EC50 = 0.5012 nM 9.3 Agonist activity at dopamine D2 receptor short isoform (unknown origin) expresse... -
D(2) dopamine receptor Ki = 0.527 nM 9.28 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
D(3) dopamine receptor IC50 = 0.596 nM 9.22 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(2) dopamine receptor Ki = 0.62 nM 9.21 Binding affinity to dopamine D2 receptor (unknown origin) assessed as inhibition... 38516587
D(2) dopamine receptor IC50 = 1.582 nM 8.8 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
5-hydroxytryptamine receptor 2A EC50 = 1.778 nM 8.75 Agonist activity at 5HT2A receptor (unknown origin) expressed in mouse NIH/3T3 c... -
Alpha-1B adrenergic receptor Ki = 1.964 nM 8.71 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Alpha-1A adrenergic receptor Ki = 2.817 nM 8.55 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
5-hydroxytryptamine receptor 1A Ki = 3.22 nM 8.49 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor IC50 = 3.547 nM 8.45 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(2) dopamine receptor Kd = 4.0 nM 8.4 In vitro affinity at mutant D2 receptor (S197A) in C6 (glioma) cell membranes. 10956209
5-hydroxytryptamine receptor 2B Ki = 5.292 nM 8.28 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Alpha-2A adrenergic receptor Ki = 5.533 nM 8.26 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
5-hydroxytryptamine receptor 1A IC50 = 5.635 nM 8.25 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Alpha-1A adrenergic receptor IC50 = 6.96 nM 8.16 DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) -
D(2) dopamine receptor Kd = 8.0 nM 8.1 In vitro affinity at mutant D2 receptor (S194A) in C6 (glioma) cell membranes. 10956209
D(2) dopamine receptor Kd = 8.0 nM 8.1 In vitro affinity at wild type Dopamine receptor D2 on C6 (glioma) cell membrane... 10956209
5-hydroxytryptamine receptor 2B IC50 = 8.316 nM 8.08 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
D(2) dopamine receptor Ki = 10.0 nM 8.0 Binding affinity to D2 receptor (unknown origin) assessed as inhibition constant 39038276

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 81
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32676143 10.1021/acsmedchemlett.0c00042 Unchecked 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3712375 10.1021/jm00156a027 Rattus norvegicus 6
21474681 10.1124/dmd.111.038778 Brain 5
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 5
3950903 10.1021/jm00152a004 Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 4
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 4
38516587 10.1039/d3md00677h ADMET 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 4
10956209 10.1021/jm990526y D(2) dopamine receptor 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
32676143 10.1021/acsmedchemlett.0c00042 N-acetylgalactosamine-6-sulfatase 4

Data from ChEMBL 36 via Core Engine