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Compound Detail

CHEMBL1065

METHYSERGIDE
💊 Approved Drug
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💊 Approved Drug
CC[C@@H](CO)NC(=O)[C@@H]1C=C2c3cccc4c3c(cn4C)C[C@H]2N(C)C1

Basic Information

ChEMBL ID CHEMBL1065
Name METHYSERGIDE
Phase Approved
Structure Type MOL
InChI Key KPJZHOPZRAFDTN-ZRGWGRIASA-N
Therapeutic ✓ Yes

Known Names

Deseril Methysergide Metisergida
21
Targets
52
Activities
2
Assay Types
1
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

353.5
MW (Da)
1.94
ALogP
4
HBA
2
HBD
57.5
PSA (Ų)
0.88
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1962
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -erg-
USAN Year 1970

Extended Properties

Molecular Formula C21H27N3O2
MW 353.47
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.74

Indications

Migraine Disorders

ATC Classification

N02CA04
methysergide
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

Ki 31 meas. best 9.45
IC50 21 meas. best 9.25

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 9.45 8.5633 0.4 3
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 9.25 9.25 0.6 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 8.96 8.78 1.1 2
5-hydroxytryptamine receptor 2A
CHEMBL322
Ki 8.84 8.78 1.4 3
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
Ki 8.84 8.56 1.4 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.8 8.4067 1.6 3
Rattus norvegicus
CHEMBL376
Ki 8.72 8.445 1.9 2
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 8.68 8.68 2.1 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
IC50 8.3 8.3 5.0 1
Unchecked
CHEMBL612545
Ki 8.24 7.104 5.7 5
Rattus norvegicus
CHEMBL376
IC50 8.13 8.0 7.4 2
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 7.9 7.5 12.6 2
5-hydroxytryptamine receptor 7
CHEMBL3223
Ki 7.9 7.9 12.6 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.89 7.89 13.0 1
Unchecked
CHEMBL612545
IC50 7.7 6.25 20.0 3
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 7.51 7.51 31.0 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
IC50 7.5 7.5 31.6 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 7.27 7.27 54.0 1
D(3) dopamine receptor
CHEMBL234
Ki 7.23 7.23 59.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.12 7.12 75.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 6.97 6.97 108.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.79 6.79 162.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.76 6.76 172.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 6.75 6.75 177.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.57 6.57 269.0 1
Plasmodium berghei
CHEMBL612653
IC50 6.45 6.45 356.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.33 6.33 472.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.21 6.21 611.0 1
D(2) dopamine receptor
CHEMBL217
IC50 6.09 6.09 807.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.04 6.04 912.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.03 6.03 943.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.79 5.79 1631.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.66 5.66 2175.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.32 5.32 4763.0 1
Bile salt export pump
CHEMBL6020
IC50 4.48 4.48 33070.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 13.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2B Ki = 0.358 nM 9.45 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 0.563 nM 9.25 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C Ki = 1.093 nM 8.96 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Serotonin 2 (5-HT2) receptor Ki = 1.445 nM 8.84 Tested for the binding affinity towards 5-HT2 receptor measured by [3H]ketanseri... -
5-hydroxytryptamine receptor 2A Ki = 1.445 nM 8.84 Inhibition of [3H]ketanserin binding to 5-hydroxytryptamine 2A receptor rat fron... 7914540
5-hydroxytryptamine receptor 2A Ki = 1.585 nM 8.8 Displacement of [3H]ketanserin from human 5HT2AR expressed in CHOK1 cells 23043420
5-hydroxytryptamine receptor 2A Ki = 1.6 nM 8.8 Binding affinity to 5-hydroxytryptamine 2A receptor from rat cortex assayed usin... 7629808
Rattus norvegicus Ki = 1.92 nM 8.72 Compound was evaluated for its activity at membrane-bound receptor (M+L+P fracti... 3746815
5-hydroxytryptamine receptor 2A Ki = 1.995 nM 8.7 The compound was tested for the binding affinity against 5-hydroxytryptamine 2A ... 10543880
5-hydroxytryptamine receptor 2C IC50 = 2.087 nM 8.68 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C Ki = 2.5 nM 8.6 Displacement of [N-methyl-3H]LSD from human 5HT2C receptor expressed in HEK293 c... 17067154
5-hydroxytryptamine receptor 2A Ki = 3.832 nM 8.42 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Serotonin 2 (5-HT2) receptor IC50 = 5.012 nM 8.3 Tested for 5-hydroxytryptamine 2 receptor binding ability by displacement of [3H... 3681895
Serotonin 2 (5-HT2) receptor Ki = 5.3 nM 8.28 Binding affinity which represents concentration giving half-maximal inhibition o... 9748351
Unchecked Ki = 5.7 nM 8.24 Displacement of [3H]ketanserin from 5HT2A receptor in rabbit cerebral cortex mem... 9214741
Unchecked Ki = 6.8 nM 8.17 Displacement of [3H]ketanserin from 5HT2 receptor 8496700
Rattus norvegicus Ki = 6.74 nM 8.17 Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solu... 3746815
Rattus norvegicus IC50 = 7.413 nM 8.13 Compound was evaluated for its activity at membrane-bound receptor (M+L+P fracti... 3746815
5-hydroxytryptamine receptor 2B Ki = 7.586 nM 8.12 Displacement of [3H]LSD from 5-HT2B receptor (unknown origin) 24365159
5-hydroxytryptamine receptor 2B Ki = 7.6 nM 8.12 Displacement of [3H]LSD from 5-HT2B receptor (unknown origin) 24365159

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3746815 10.1021/jm00159a017 Rattus norvegicus 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
7798965 10.1021/np50111a020 Ileum 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
8496700 10.1021/np50094a001 Unchecked 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Histamine H2 receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
24365159 10.1016/j.bmcl.2013.12.024 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine