Compound Detail
CHEMBL442
ERGOTAMINE 💊 Approved Drug
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💊 Approved Drug
CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)C[C@H]21
Basic Information
| ChEMBL ID | CHEMBL442 |
| Name | ERGOTAMINE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | XCGSFFUVFURLIX-VFGNJEKYSA-N |
| Therapeutic | ✓ Yes |
31
Targets
64
Activities
3
Assay Types
7
PK Parameters
20
Publications
3
Known Names
2
Indications
Molecular Properties
581.7
MW (Da)
1.99
ALogP
6
HBA
3
HBD
118.2
PSA (Ų)
0.43
QED
1
Ro5 Violations
4
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1948 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Indications
Migraine Disorders Hypotension, Orthostatic
ATC Classification
N02CA02
ergotamine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02CA52
ergotamine, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02CA72
ergotamine, combinations with psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
Activity Summary
Ki 36 meas. best 10.04
IC50 26 meas. best 9.7
EC50 2 meas. best 8.14
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1B CHEMBL3459 | Ki | 10.04 | 10.04 | 0.1 | 1 |
| 5-hydroxytryptamine receptor 1B CHEMBL3459 | IC50 | 9.7 | 9.7 | 0.2 | 1 |
| 5-hydroxytryptamine receptor 1A CHEMBL273 | Ki | 9.35 | 9.35 | 0.4 | 1 |
| 5-hydroxytryptamine receptor 1A CHEMBL273 | IC50 | 9.11 | 9.11 | 0.8 | 1 |
| Alpha-2A adrenergic receptor CHEMBL1867 | Ki | 9.1 | 9.1 | 0.8 | 1 |
| 5-hydroxytryptamine receptor 1D CHEMBL1983 | Ki | 9.1 | 8.586 | 0.8 | 5 |
| 5-hydroxytryptamine receptor 6 CHEMBL3371 | Ki | 9.02 | 9.02 | 0.9 | 1 |
| D(2) dopamine receptor CHEMBL217 | Ki | 8.84 | 8.84 | 1.4 | 1 |
| D(3) dopamine receptor CHEMBL234 | Ki | 8.83 | 8.83 | 1.5 | 1 |
| Alpha-2B adrenergic receptor CHEMBL1942 | Ki | 8.76 | 8.76 | 1.8 | 1 |
| Alpha-2C adrenergic receptor CHEMBL1916 | Ki | 8.74 | 8.74 | 1.8 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | Ki | 8.73 | 8.73 | 1.9 | 1 |
| 5-hydroxytryptamine receptor 6 CHEMBL3371 | IC50 | 8.69 | 8.69 | 2.0 | 1 |
| 5-hydroxytryptamine receptor 1B CHEMBL1898 | Ki | 8.68 | 8.57 | 2.1 | 3 |
| Alpha-2A adrenergic receptor CHEMBL1867 | IC50 | 8.67 | 8.67 | 2.1 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | Ki | 8.66 | 8.66 | 2.2 | 1 |
| Unchecked CHEMBL612545 | Ki | 8.61 | 8.61 | 2.4 | 1 |
| Alpha-1A adrenergic receptor CHEMBL319 | Ki | 8.49 | 8.49 | 3.3 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | IC50 | 8.46 | 8.46 | 3.5 | 1 |
| Unchecked CHEMBL612545 | IC50 | 8.44 | 8.44 | 3.6 | 1 |
| Alpha-2B adrenergic receptor CHEMBL1942 | IC50 | 8.41 | 8.41 | 3.8 | 1 |
| D(2) dopamine receptor CHEMBL217 | IC50 | 8.37 | 8.37 | 4.3 | 1 |
| D(3) dopamine receptor CHEMBL234 | IC50 | 8.37 | 8.37 | 4.3 | 1 |
| Alpha-1B adrenergic receptor CHEMBL315 | Ki | 8.34 | 8.34 | 4.5 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | IC50 | 8.19 | 8.19 | 6.5 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | EC50 | 8.14 | 8.12 | 7.3 | 2 |
| Alpha-1A adrenergic receptor CHEMBL319 | IC50 | 8.09 | 8.09 | 8.1 | 1 |
| Alpha-1B adrenergic receptor CHEMBL315 | IC50 | 8.09 | 8.09 | 8.2 | 1 |
| Alpha-2C adrenergic receptor CHEMBL1916 | IC50 | 7.92 | 7.92 | 12.0 | 1 |
| 5-hydroxytryptamine receptor 5A CHEMBL3426 | Ki | 7.85 | 7.704 | 14.0 | 5 |
| Alpha-1D adrenergic receptor CHEMBL223 | Ki | 7.62 | 7.62 | 24.0 | 1 |
| 5-hydroxytryptamine receptor 2C CHEMBL225 | Ki | 7.54 | 7.54 | 29.0 | 1 |
| Alpha-1D adrenergic receptor CHEMBL223 | IC50 | 7.31 | 7.31 | 49.0 | 1 |
| 5-hydroxytryptamine receptor 2C CHEMBL225 | IC50 | 7.25 | 7.25 | 56.0 | 1 |
| 5-hydroxytryptamine receptor 4 CHEMBL5017 | Ki | 6.58 | 6.58 | 264.0 | 1 |
| D(1A) dopamine receptor CHEMBL2056 | Ki | 6.06 | 6.06 | 864.0 | 1 |
| Cytochrome P450 3A4 CHEMBL340 | IC50 | 6.0 | 6.0 | 1000.0 | 1 |
| 5-hydroxytryptamine receptor 4 CHEMBL5017 | IC50 | 5.8 | 5.8 | 1584.0 | 1 |
| D(1A) dopamine receptor CHEMBL2056 | IC50 | 5.76 | 5.76 | 1728.0 | 1 |
| Beta-2 adrenergic receptor CHEMBL210 | Ki | 5.72 | 5.72 | 1898.0 | 1 |
| Beta-1 adrenergic receptor CHEMBL213 | Ki | 5.62 | 5.62 | 2392.0 | 1 |
| Beta-2 adrenergic receptor CHEMBL210 | IC50 | 5.56 | 5.56 | 2761.0 | 1 |
| Thromboxane-A synthase CHEMBL1835 | IC50 | 5.51 | 5.51 | 3064.0 | 1 |
| Tyrosine-protein kinase Fyn CHEMBL1841 | IC50 | 5.5 | 5.5 | 3160.0 | 1 |
| Beta-1 adrenergic receptor CHEMBL213 | IC50 | 5.38 | 5.38 | 4142.0 | 1 |
| Tyrosine-protein kinase Lck CHEMBL258 | IC50 | 5.19 | 5.19 | 6499.0 | 1 |
| ATP-dependent translocase ABCB1 CHEMBL4302 | Ki | 4.85 | 4.425 | 14250.0 | 2 |
| Gastrin/cholecystokinin type B receptor CHEMBL2854 | IC50 | 4.77 | 4.77 | 17000.0 | 1 |
| ATP-dependent translocase ABCB1 CHEMBL3467 | Ki | 4.75 | 4.75 | 18000.0 | 1 |
| Cholecystokinin receptor type A CHEMBL2798 | IC50 | 4.47 | 4.47 | 34000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 15.0 | mL.min-1.kg-1 | Homo sapiens |
| Fu | 0.02 | - | - |
| Fu | 0.003 | - | - |
| Fu | 0.02 | - | Homo sapiens |
| Fu | 0.02 | - | Homo sapiens |
| MRT | 4.0 | hr | Homo sapiens |
| T1/2 | 2.1 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine