Compound Detail

CHEMBL19215

METERGOLINE

🧪 Phase II

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🧪 Phase II

CN1C[C@H](CNC(=O)OCc2ccccc2)C[C@@H]2c3cccc4c3c(cn4C)C[C@H]21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL19215
Name	METERGOLINE
Phase	Phase II
Structure Type	MOL
InChI Key	WZHJKEUHNJHDLS-QTGUNEKASA-N
Therapeutic	✓ Yes

Known Names

FI 6337 FI-6337 Liserdol MCE Metergolina Metergoline NSC-755878

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

403.5

MW (Da)

4.06

ALogP

HBA

HBD

46.5

PSA (Å²)

0.71

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-erg-

Extended Properties

Molecular Formula	C25H29N3O2
MW	403.53
Aromatic Rings	3
Heavy Atoms	30
NP-Likeness	0.33

ATC Classification

G02CB05

metergoline

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: OTHER GYNECOLOGICALS

Activity Summary

IC50 39 meas. best 9.4

Ki 38 meas. best 9.95

EC50 5 meas. best 8.12

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	9.95	9.95	0.1	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	9.55	9.55	0.3	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	9.52	9.26	0.3	2
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	9.46	9.38	0.3	2
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	9.4	9.4	0.4	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	9.36	9.36	0.4	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	9.18	9.18	0.7	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	8.64	8.265	2.3	2
D(3) dopamine receptor CHEMBL234	Ki	8.58	8.58	2.6	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	8.45	8.335	3.5	2
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	8.39	8.39	4.1	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	8.21	8.21	6.2	1
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	8.2	8.2	6.3	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	8.2	8.2	6.3	3
Alpha-2B adrenergic receptor CHEMBL1942	Ki	8.12	8.12	7.5	1
5-hydroxytryptamine receptor 1A CHEMBL214	EC50	8.12	8.12	7.5	1
D(3) dopamine receptor CHEMBL234	IC50	8.11	8.11	7.7	1
5-hydroxytryptamine receptor 1B CHEMBL3459	Ki	7.96	7.78	11.0	2
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	7.89	7.89	13.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.8	7.8	16.0	1
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	7.72	7.72	19.0	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	Ki	7.7	7.7	20.0	1
D(2) dopamine receptor CHEMBL217	Ki	7.68	7.68	21.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	7.66	7.66	22.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.57	7.57	27.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	7.55	7.55	28.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	7.43	7.43	37.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	7.42	7.42	38.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	7.3	7.3	50.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	7.24	7.24	58.0	1
D(2) dopamine receptor CHEMBL217	IC50	7.2	7.2	63.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	7.2	7.2	63.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	7.17	7.17	67.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	7.13	7.13	74.0	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	7.02	7.02	95.0	1
Alpha-1D adrenergic receptor CHEMBL223	IC50	6.87	6.87	136.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.84	6.84	145.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	6.72	6.72	189.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.7	6.7	200.0	1
Unchecked CHEMBL612545	Ki	6.62	6.305	238.0	4
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.58	6.58	262.0	1
Unchecked CHEMBL612545	IC50	6.57	6.2375	268.0	4
5-hydroxytryptamine receptor 4 CHEMBL5017	Ki	6.56	6.56	274.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	6.5	6.5	313.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.44	6.44	363.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.44	6.44	366.0	1
Histamine H1 receptor CHEMBL231	Ki	6.32	6.32	480.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	6.23	6.23	590.0	1
Histamine H2 receptor CHEMBL1941	Ki	6.02	6.02	959.0	1
Histamine H2 receptor CHEMBL1941	IC50	6.01	6.01	975.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
F	23.0	%	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2A	Ki	=	0.113	nM	9.95	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2B	Ki	=	0.281	nM	9.55	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
Serotonin 2 (5-HT2) receptor	Ki	=	0.3	nM	9.52	Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) rece...	3543362
5-hydroxytryptamine receptor 2C	Ki	=	0.347	nM	9.46	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2A	IC50	=	0.395	nM	9.4	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2B	IC50	=	0.442	nM	9.36	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2C	Ki	=	0.5	nM	9.3	Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptam...	3543362
5-hydroxytryptamine receptor 2C	IC50	=	0.663	nM	9.18	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Serotonin 2 (5-HT2) receptor	Ki	=	1.0	nM	9.0	Binding affinity to 5-hydroxytryptamine 2 receptor in rat frontal cortical membr...	3543362
5-hydroxytryptamine receptor 1A	Ki	=	2.3	nM	8.64	Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in...	23403082
D(3) dopamine receptor	Ki	=	2.611	nM	8.58	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
5-hydroxytryptamine receptor 1A	Ki	=	3.528	nM	8.45	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 1A	IC50	=	4.1	nM	8.39	Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in...	23403082
5-hydroxytryptamine receptor 1A	Ki	=	6.0	nM	8.22	Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox...	3543362
5-hydroxytryptamine receptor 1A	IC50	=	6.175	nM	8.21	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 7	Ki	=	6.31	nM	8.2	Non-selective inhibitory activity was determined against 5-hydroxytryptamine 7 r...	14667218
5-hydroxytryptamine receptor 7	Ki	=	6.31	nM	8.2	Binding affinity towards 5-hydroxytryptamine 7 receptor	10843226
5-hydroxytryptamine receptor 7	Ki	=	6.31	nM	8.2	Displacement of [3H]5CT from 5HT7 receptor	20346662
5-hydroxytryptamine receptor 7	Ki	=	6.31	nM	8.2	Displacement of [3H]5-HT from recombinant human 5-HT7 receptor expressed in Afri...	31581003
Alpha-2B adrenergic receptor	Ki	=	7.516	nM	8.12	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-

Literature References

PubMed	DOI	Target Context	# Activities
19734910	10.1038/nchembio.215	Plasmodium falciparum	7
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
23415087	10.1016/j.bmc.2013.01.033	Heparanase	3
23403082	10.1016/j.bmcl.2013.01.025	5-hydroxytryptamine receptor 1A	3
3543362	10.1021/jm00384a001	Serotonin 2 (5-HT2) receptor	3
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
37468498	10.1038/s41467-023-40064-9	Sodium-dependent serotonin transporter	2
17417631	10.1038/nchembio873	NON-PROTEIN TARGET	2
17417631	10.1038/nchembio873	Unchecked	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	2
-	10.1039/C3MD00310H	Plasmodium falciparum	2
37468498	10.1038/s41467-023-40064-9	Thromboxane A2 receptor	2
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	2
12438524	10.1124/jpet.102.039255	ATP-dependent translocase ABCB1	2
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	2
20451398	10.1016/j.bmc.2010.04.039	ADMET	2
39037114	10.1021/acs.jmedchem.4c00861	Sodium channel protein type 2 subunit alpha	1
3543362	10.1021/jm00384a001	5-hydroxytryptamine receptor 1B	1

Data from ChEMBL 36 via Core Engine