Compound Detail

CHEMBL1732

DIHYDROERGOTAMINE

💊 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[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1732
Name	DIHYDROERGOTAMINE
Phase	Approved
Structure Type	MOL
InChI Key	LUZRJRNZXALNLM-JGRZULCMSA-N
Therapeutic	✓ Yes

Known Names

9,10-dihydroergotamine Dihidroergotamina Dihydroergotamine MAP-0004 MAP0004 Neomigran

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

583.7

MW (Da)

2.08

ALogP

HBA

HBD

118.2

PSA (Å²)

0.43

QED

Ro5 Violations

Rot. Bonds

Drug Information

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

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product

USAN Stem	-erg-
USAN Year	1965

Extended Properties

Molecular Formula	C33H37N5O5
MW	583.69
Aromatic Rings	3
Heavy Atoms	43
NP-Likeness	0.83

Indications

Migraine Disorders Migraine with Aura Migraine without Aura

ATC Classification

N02CA01

dihydroergotamine

Level 1: NERVOUS SYSTEM

Level 2: ANALGESICS

N02CA51

dihydroergotamine, combinations

Level 1: NERVOUS SYSTEM

Level 2: ANALGESICS

Activity Summary

IC50 26 meas. best 9.18

Ki 20 meas. best 9.42

Kd 3 meas. best 7.55

EC50 1 meas. best 5.19

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	9.42	9.42	0.4	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	9.42	9.42	0.4	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	9.41	9.41	0.4	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	9.18	9.18	0.7	1
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	9.07	9.07	0.8	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	8.99	8.99	1.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	8.83	8.83	1.5	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	8.82	8.82	1.5	1
Unchecked CHEMBL612545	Ki	8.78	7.06	1.7	2
Alpha-2B adrenergic receptor CHEMBL1942	Ki	8.75	8.75	1.8	1
D(3) dopamine receptor CHEMBL234	Ki	8.74	8.74	1.8	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	8.69	8.69	2.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	8.64	8.64	2.3	1
Unchecked CHEMBL612545	IC50	8.6	6.95	2.5	2
D(2) dopamine receptor CHEMBL217	Ki	8.53	8.53	3.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	8.49	8.49	3.2	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	8.43	8.395	3.7	2
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	8.43	8.43	3.7	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	8.41	8.41	3.9	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	8.35	8.35	4.5	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	8.3	8.3	5.0	1
D(3) dopamine receptor CHEMBL234	IC50	8.27	8.27	5.3	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	8.17	8.17	6.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	8.1	8.1	8.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	8.09	8.09	8.1	1
D(2) dopamine receptor CHEMBL217	IC50	8.05	8.05	8.9	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	8.0	8.0	10.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	7.85	7.85	14.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	7.57	7.57	27.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	7.55	7.55	28.2	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	7.54	7.54	29.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	7.33	7.33	47.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	Kd	7.25	7.25	56.2	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	7.05	7.05	90.0	1
5-hydroxytryptamine receptor 4 CHEMBL5017	Ki	6.8	6.8	157.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	6.68	6.68	208.9	1
5-hydroxytryptamine receptor 4 CHEMBL5017	IC50	6.03	6.03	940.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	5.92	5.92	1197.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	5.62	5.62	2395.0	1
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	5.55	5.55	2800.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	5.52	5.41	2999.2	2
Unchecked CHEMBL612545	EC50	5.19	5.19	6440.0	1
Multidrug and toxin extrusion protein 2 CHEMBL1743127	IC50	4.9	4.9	12600.0	1
Gastrin/cholecystokinin type B receptor CHEMBL2854	IC50	4.64	4.64	23000.0	1
Solute carrier family 22 member 2 CHEMBL1743122	IC50	4.3	4.3	49900.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	9.0	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1A	Ki	=	0.377	nM	9.42	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 1B	Ki	=	0.384	nM	9.42	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: ...	-
Alpha-2A adrenergic receptor	Ki	=	0.387	nM	9.41	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
5-hydroxytryptamine receptor 1A	IC50	=	0.659	nM	9.18	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 1B	IC50	=	0.846	nM	9.07	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: ...	-
Alpha-2A adrenergic receptor	IC50	=	1.032	nM	8.99	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
5-hydroxytryptamine receptor 6	Ki	=	1.486	nM	8.83	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [...	-
Alpha-2C adrenergic receptor	Ki	=	1.51	nM	8.82	DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912)	-
Unchecked	Ki	=	1.669	nM	8.78	DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan)	-
Alpha-2B adrenergic receptor	Ki	=	1.766	nM	8.75	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-
D(3) dopamine receptor	Ki	=	1.812	nM	8.74	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Alpha-1A adrenergic receptor	Ki	=	2.035	nM	8.69	DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin)	-
5-hydroxytryptamine receptor 2A	Ki	=	2.273	nM	8.64	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
Unchecked	IC50	=	2.503	nM	8.6	DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan)	-
D(2) dopamine receptor	Ki	=	2.96	nM	8.53	DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone)	-
5-hydroxytryptamine receptor 6	IC50	=	3.201	nM	8.49	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [...	-
5-hydroxytryptamine receptor 2B	Ki	=	3.7	nM	8.43	Binding affinity to 5-HT2B receptor (unknown origin) assessed as inhibition cons...	38516587
Adrenergic receptor alpha-2	IC50	=	3.7	nM	8.43	Inhibition of specific [3H]clonidine binding (0.4 nM) to rat brain membranes alp...	6142954
Alpha-2B adrenergic receptor	IC50	=	3.867	nM	8.41	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-
5-hydroxytryptamine receptor 2B	Ki	=	4.33	nM	8.36	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	29
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
6142954	10.1021/jm00370a011	Adrenergic receptor alpha-2	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	3
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	3
6142954	10.1021/jm00370a011	Adrenergic receptor alpha-1	3
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	2
37468498	10.1038/s41467-023-40064-9	D(1A) dopamine receptor	2
37468498	10.1038/s41467-023-40064-9	Beta-2 adrenergic receptor	2
6142954	10.1021/jm00370a011	Adrenergic receptor alpha	2
11961113	10.1124/mol.61.5.964	ATP-dependent translocase ABCB1	2
12235267	10.1124/jpet.102.037549	ATP-dependent translocase ABCB1	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
23241029	10.1021/jm301302s	Multidrug and toxin extrusion protein 1	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
24183589	10.1016/j.bmc.2013.09.022	Unchecked	2
26948801	10.1016/j.drudis.2016.02.015	Homo sapiens	2

Data from ChEMBL 36 via Core Engine