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Compound Detail

CHEMBL1201356

METHYLERGONOVINE
💊 Approved Drug
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💊 Approved Drug
CC[C@@H](CO)NC(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1

Basic Information

ChEMBL ID CHEMBL1201356
Name METHYLERGONOVINE
Phase Approved
Structure Type MOL
InChI Key UNBRKDKAWYKMIV-QWQRMKEZSA-N
Therapeutic ✓ Yes

Known Names

Ergotyl Methylergometrine Methylergonovine Metilergometrina
13
Targets
27
Activities
3
Assay Types
3
PK Parameters
20
Publications
4
Known Names

Molecular Properties

339.4
MW (Da)
1.92
ALogP
3
HBA
3
HBD
68.4
PSA (Ų)
0.80
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1946
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -erg-; -vin-

Extended Properties

Molecular Formula C20H25N3O2
MW 339.44
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.91

ATC Classification

G02AB01
methylergometrine
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: OTHER GYNECOLOGICALS

Activity Summary

IC50 13 meas. best 8.82
Ki 13 meas. best 9.14
EC50 1 meas. best 7.67

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 9.14 9.14 0.7 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 9.1 9.06 0.8 2
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 8.93 8.93 1.2 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 8.82 8.82 1.5 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 8.63 8.63 2.3 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 8.6 8.6 2.5 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 8.59 8.59 2.5 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 8.39 8.39 4.1 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 8.18 8.18 6.6 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 8.03 8.03 9.3 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.89 7.89 13.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
IC50 7.82 7.82 15.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
EC50 7.67 7.67 21.4 1
D(3) dopamine receptor
CHEMBL234
Ki 7.24 7.24 57.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.78 6.78 167.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.7 6.7 200.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.68 6.68 210.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.56 6.56 276.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.34 6.34 461.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.27 6.27 539.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.22 6.22 596.0 1
D(2) dopamine receptor
CHEMBL217
IC50 6.08 6.08 829.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 5.97 5.97 1077.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.8 5.8 1590.0 1
Unchecked
CHEMBL612545
Ki 5.71 5.71 1956.0 1
Unchecked
CHEMBL612545
IC50 5.53 5.53 2934.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 40.0 % Homo sapiens
T1/2 2.5 hr Rattus norvegicus
Vd 2.4 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.728 nM 9.14 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B Ki = 0.8 nM 9.1 Displacement of [3H]LSD from human cloned 5HT2B receptor expressed in CHO cells ... 20958049
5-hydroxytryptamine receptor 2B Ki = 0.958 nM 9.02 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 6 Ki = 1.178 nM 8.93 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
5-hydroxytryptamine receptor 2B IC50 = 1.505 nM 8.82 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 1A Ki = 2.326 nM 8.63 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 6 IC50 = 2.538 nM 8.6 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
5-hydroxytryptamine receptor 2A IC50 = 2.547 nM 8.59 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 1A IC50 = 4.07 nM 8.39 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C Ki = 6.558 nM 8.18 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 1B Ki = 9.263 nM 8.03 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C IC50 = 13.0 nM 7.89 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 1B IC50 = 15.0 nM 7.82 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B EC50 = 21.38 nM 7.67 Agonist at human 5HT2B receptor expressed in HEK293 cells assessed as induction ... 20958049
D(3) dopamine receptor Ki = 57.0 nM 7.24 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
D(3) dopamine receptor IC50 = 167.0 nM 6.78 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Cytochrome P450 2D6 IC50 = 200.0 nM 6.7 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Alpha-2B adrenergic receptor Ki = 210.0 nM 6.68 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
D(2) dopamine receptor Ki = 276.0 nM 6.56 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
Alpha-2B adrenergic receptor IC50 = 461.0 nM 6.34 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -

Literature References

PubMed DOI Target Context # Activities
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
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
38516587 10.1039/d3md00677h ADMET 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
20958049 10.1021/jm100600y 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
23241029 10.1021/jm301302s Multidrug and toxin extrusion protein 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 Glutamate receptor ionotropic, NMDA 1 1
37468498 10.1038/s41467-023-40064-9 Beta-1 adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1

Data from ChEMBL 36 via Core Engine