Compound Detail

CHEMBL1200517

DIHYDROERGOTAMINE MESYLATE

💊 Approved Drug

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

💊 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.CS(=O)(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1200517
Name	DIHYDROERGOTAMINE MESYLATE
Phase	Approved
Structure Type	MOL
InChI Key	ADYPXRFPBQGGAH-UMYZUSPBSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL1732
Active Moiety	CHEMBL1732

Known Names

D.h.e. 45 DHE-45 Diergo Dihydergot Dihydroergotamine mesilate Dihydroergotamine mesylate Dihydroergotamine mesylate component of embolex Dihydroergotamine methanesulfonate Migranal NSC-759848 Tonopan Trudhesa

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

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	C34H41N5O8S
MW	679.80
Aromatic Rings	3
Heavy Atoms	43
NP-Likeness	0.83

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin 1d (5-HT1d) receptor agonist	AGONIST	5-hydroxytryptamine receptor 1D	✓	✓

Indications

Migraine Disorders

Drug Warnings

Black Box Warning

General Warning

Country: United States

Activity Summary

IC50 72 meas. best 7.66

Ki 20 meas. best 7.87

EC50 5 meas. best 5.72

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.87	7.87	13.6	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	7.83	7.83	14.6	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.7	7.7	19.8	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	7.68	7.68	21.1	1
Plasmodium falciparum CHEMBL364	IC50	7.66	6.0125	22.0	72
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	7.5	7.5	31.3	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	7.48	7.48	32.9	1
D(4) dopamine receptor CHEMBL219	Ki	7.48	7.48	32.8	1
D(3) dopamine receptor CHEMBL234	Ki	7.47	7.47	34.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.41	7.41	39.1	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	7.22	7.22	60.2	1
D(2) dopamine receptor CHEMBL217	Ki	7.21	7.21	60.9	1
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.97	6.97	107.9	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	6.92	6.92	118.7	1
Mu-type opioid receptor CHEMBL233	Ki	6.81	6.81	154.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.67	6.67	214.2	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.65	6.65	224.6	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.22	6.22	603.7	1
5-hydroxytryptamine receptor 1E CHEMBL2182	Ki	6.17	6.17	682.2	1
Glucose-dependent insulinotropic receptor CHEMBL5652	EC50	5.72	5.72	1914.2	1
Apelin receptor CHEMBL1628481	EC50	5.66	5.66	2188.9	1
Glucagon-like peptide 1 receptor CHEMBL1784	EC50	5.62	5.62	2404.6	1
Free fatty acid receptor 4 CHEMBL5339	EC50	5.59	5.59	2571.8	1
Beta-2 adrenergic receptor CHEMBL210	EC50	5.55	5.55	2830.0	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	5.55	5.55	2843.5	1
D(1B) dopamine receptor CHEMBL1850	Ki	5.53	5.53	2948.8	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-2B adrenergic receptor	Ki	=	13.57	nM	7.87	PDSP Secondary Binding target: ADRA2B - Compounds are tested at 10 uM concentrat...	-
Alpha-2A adrenergic receptor	Ki	=	14.62	nM	7.83	PDSP Secondary Binding target: ADRA2A - Compounds are tested at 10 uM concentrat...	-
Alpha-2C adrenergic receptor	Ki	=	19.76	nM	7.7	PDSP Secondary Binding target: ADRA2C - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 2A	Ki	=	21.05	nM	7.68	PDSP Secondary Binding target: HTR2A - Compounds are tested at 10 uM concentrati...	-
Plasmodium falciparum	IC50	=	22.0	nM	7.66	Antiplasmodial activity against Plasmodium falciparum CDY harboring modified mdr...	19734910
5-hydroxytryptamine receptor 5A	Ki	=	31.3	nM	7.5	PDSP Secondary Binding target: HTR5A - Compounds are tested at 10 uM concentrati...	-
D(4) dopamine receptor	Ki	=	32.82	nM	7.48	PDSP Secondary Binding target: DRD4 - Compounds are tested at 10 uM concentratio...	-
Alpha-1A adrenergic receptor	Ki	=	32.9	nM	7.48	PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat...	-
D(3) dopamine receptor	Ki	=	33.96	nM	7.47	PDSP Secondary Binding target: DRD3 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 1A	Ki	=	39.06	nM	7.41	PDSP Secondary Binding target: HTR1A - Compounds are tested at 10 uM concentrati...	-
Plasmodium falciparum	IC50	=	42.0	nM	7.38	Antiplasmodial activity against Plasmodium falciparum CDY harboring modified mdr...	19734910
5-hydroxytryptamine receptor 7	Ki	=	60.17	nM	7.22	PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio...	-
D(2) dopamine receptor	Ki	=	60.92	nM	7.21	PDSP Secondary Binding target: DRD2 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 1B	Ki	=	107.89	nM	6.97	PDSP Secondary Binding target: HTR1B - Compounds are tested at 10 uM concentrati...	-
Alpha-1B adrenergic receptor	Ki	=	118.74	nM	6.92	PDSP Secondary Binding target: ADRA1B - Compounds are tested at 10 uM concentrat...	-
Plasmodium falciparum	IC50	=	128.0	nM	6.89	Antiplasmodial activity against Plasmodium falciparum JC3 after 72 hrs by SYBR g...	19734910
Mu-type opioid receptor	Ki	=	154.01	nM	6.81	PDSP Secondary Binding target: OPRM1 - Compounds are tested at 10 uM concentrati...	-
Plasmodium falciparum	IC50	=	159.1	nM	6.8	Antiplasmodial activity against Plasmodium falciparum JF6 after 72 hrs by SYBR g...	19734910
Plasmodium falciparum	IC50	=	157.0	nM	6.8	Antiplasmodial activity against Plasmodium falciparum JF11 after 72 hrs by SYBR ...	19734910
Plasmodium falciparum	IC50	=	179.9	nM	6.75	Antiplasmodial activity against Plasmodium falciparum WE2 after 72 hrs by SYBR g...	19734910

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5724801	U2OS	304
-	10.6019/CHEMBL5058577	Fibroblast	304
-	10.6019/CHEMBL5724801	Fibroblast	304
-	10.6019/CHEMBL5724801	HEK-293T	304
-	10.6019/CHEMBL5058577	U2OS	304
-	10.6019/CHEMBL5058577	HEK-293T	304
19734910	10.1038/nchembio.215	Plasmodium falciparum	72
-	10.6019/CHEMBL5058564	HEK-293T	4
-	10.6019/CHEMBL5058564	U2OS	3
-	10.6019/CHEMBL5058564	Fibroblast	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	2
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	2
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	2
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	2
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	2
-	10.6019/CHEMBL5209801	Apelin receptor	2
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	2
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	2
-	10.6019/CHEMBL5209801	G-protein coupled receptor 35	2

Data from ChEMBL 36 via Core Engine