Compound Detail

CHEMBL86

METOCLOPRAMIDE

💊 Approved Drug

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💊 Approved Drug

CCN(CC)CCNC(=O)c1cc(Cl)c(N)cc1OC

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL86
Name	METOCLOPRAMIDE
Phase	Approved
Structure Type	MOL
InChI Key	TTWJBBZEZQICBI-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Clopra-"yellow" Elieten Methoxyclopramide Metoclopramida Metoclopramide Terperan

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

299.8

MW (Da)

2.00

ALogP

HBA

HBD

67.6

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1979
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product

USAN Year

1964

Extended Properties

Molecular Formula	C14H22ClN3O2
MW	299.80
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	-1.54

Indications

Digestive System Diseases Gastroenteritis Gastrointestinal Hemorrhage Gastroparesis Gastroschisis Headache HIV Infections Migraine Disorders Nausea Neoplasms Postoperative Nausea and Vomiting Sepsis Vomiting Hyperemesis Gravidarum Hypoglycemia Intestinal Obstruction Myelodysplastic Syndromes Pain Wounds and Injuries Hypotension, Orthostatic

ATC Classification

A03FA01

metoclopramide

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS

Activity Summary

Ki 36 meas. best 7.8

IC50 26 meas. best 7.21

Kd 6 meas. best 7.3

EC50 4 meas. best 8.24

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 4 CHEMBL5017	EC50	8.24	8.24	5.7	1
D(3) dopamine receptor CHEMBL234	Ki	7.8	7.585	16.0	4
D(2) dopamine receptor CHEMBL217	Ki	7.38	7.285	42.0	2
Serotonin 3 (5-HT3) receptor CHEMBL2094132	Kd	7.3	6.725	50.1	4
D(3) dopamine receptor CHEMBL3138	IC50	7.21	7.21	61.3	1
D(2) dopamine receptor CHEMBL3998	Ki	7.1	7.1	80.0	1
D(2) dopamine receptor CHEMBL339	Ki	6.98	6.724	104.0	5
D(2) dopamine receptor CHEMBL217	IC50	6.9	6.9	127.0	1
Serotonin 3 (5-HT3) receptor CHEMBL2094116	Ki	6.8	6.4592	158.5	12
Serotonin 3 receptor (5HT3) CHEMBL2111333	Ki	6.7	6.7	200.0	1
D(3) dopamine receptor CHEMBL234	IC50	6.7	6.7	200.0	1
Serotonin 3 (5-HT3) receptor CHEMBL2094116	IC50	6.64	6.2533	228.0	3
Myeloperoxidase CHEMBL2439	IC50	6.46	6.46	350.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.4	6.4	401.0	1
D(2) dopamine receptor CHEMBL339	IC50	6.35	6.255	444.0	6
Unchecked CHEMBL612545	Ki	6.33	6.185	472.0	2
5-hydroxytryptamine receptor 4 CHEMBL5017	Ki	6.26	6.26	546.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.2	6.2	630.0	1
Unchecked CHEMBL612545	IC50	6.15	5.775	708.0	2
5-hydroxytryptamine receptor 4 CHEMBL4317	EC50	6.1	5.91	794.3	2
5-hydroxytryptamine receptor 4 CHEMBL1875	EC50	6.1	6.1	794.3	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.1	6.1	800.0	1
5-hydroxytryptamine receptor 4 CHEMBL4317	Ki	6.05	6.0233	900.0	3
5-hydroxytryptamine receptor 4 CHEMBL5017	IC50	6.04	6.04	912.0	1
Cytochrome P450 2D6 CHEMBL289	Ki	6.02	6.02	960.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.99	5.99	1020.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.98	5.98	1050.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.9	5.9	1248.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.62	5.62	2383.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	5.57	5.57	2721.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.43	5.43	3675.0	1
Serotonin 1 (5-HT1) receptor CHEMBL2095159	IC50	5.11	5.11	7800.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	5.11	5.11	7700.0	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	IC50	4.88	4.88	13200.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	4.48	4.48	32800.0	1
ADMET CHEMBL612558	Kd	4.05	4.05	88900.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.02	4.02	94800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	635.0	ng.hr.mL-1	Rattus norvegicus
AUC	629.0	ng.hr.mL-1	Rattus norvegicus
AUC	420.0	ng.hr.mL-1	Rattus norvegicus
AUC	418.0	ng.hr.mL-1	Rattus norvegicus
AUC	367.0	ng.hr.mL-1	Rattus norvegicus
AUC	365.0	ng.hr.mL-1	Rattus norvegicus
CL	5.7	mL.min-1.kg-1	Homo sapiens
CL	4.6	mL.min-1.kg-1	Homo sapiens
CL	5.7	mL.min-1.kg-1	Homo sapiens
CL	5.7	mL.min-1.kg-1	Homo sapiens
F	79.0	%	Homo sapiens
F	76.0	%	Homo sapiens
Fu	0.6	-	-
Fu	0.07	-	-
Fu	0.6	-	Homo sapiens
Fu	0.365	-	Rattus norvegicus
Fu	0.6	-	Homo sapiens
Fu	0.6	-	Homo sapiens
Fu	0.95	-	Homo sapiens
Fu	0.295	-	Homo sapiens
Fu	0.36	-	Rattus norvegicus
Fu	0.295	-	Sus scrofa
Fu	0.413	-	Macaca fascicularis
Fu	0.294	-	Canis lupus familiaris
Fu	0.237	-	Cavia porcellus
Fu	0.23	-	Mus musculus
Fu	0.145	-	Rattus norvegicus
Fu	0.4257	-	Rattus norvegicus
Fu	0.224	-	Rattus norvegicus
Fu	0.677	-	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 4	EC50	=	5.7	nM	8.24	5-hydroxytryptamine 4 receptor agonist activity, concentration which gave 50% in...	9046352
D(3) dopamine receptor	Ki	=	16.0	nM	7.8	Radioligand Binding Assay: The pharmacological profile of metopimazine, metopima...	-
D(3) dopamine receptor	Ki	=	16.0	nM	7.8	Radioligand Binding Assay: The pharmacological profile of metopimazine, metopima...	-
D(3) dopamine receptor	Ki	=	27.0	nM	7.57	Displacement of [125I]iodosulpiride from human Dopamine receptor D3 expressed in...	14521403
D(2) dopamine receptor	Ki	=	42.0	nM	7.38	DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone)	-
Serotonin 3 (5-HT3) receptor	Kd	=	50.12	nM	7.3	Potency at neuronal 5-hydroxytryptamine 3 receptors in the rabbit heart	2342053
Serotonin 3 (5-HT3) receptor	Kd	=	50.12	nM	7.3	Antagonistic activity against Serotonin 5-hydroxytryptamine 3 receptor in isolat...	-
D(3) dopamine receptor	IC50	=	61.3	nM	7.21	Concentration of compound required to inhibit the binding of radioligand [3H](R)...	12593651
D(2) dopamine receptor	Ki	=	64.0	nM	7.19	Radioligand Binding Assay: The pharmacological profile of metopimazine, metopima...	-
D(3) dopamine receptor	Ki	=	68.0	nM	7.17	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Serotonin 3 (5-HT3) receptor	Kd	=	79.43	nM	7.1	Evaluated for the antagonistic activity against Serotonin 5-hydroxytryptamine 3 ...	-
D(2) dopamine receptor	Ki	=	80.0	nM	7.1	Compound was evaluated for the binding affinity at Dopamine receptor D2	7608898
D(2) dopamine receptor	Ki	=	104.0	nM	6.98	Compound was evaluated for binding affinity towards DA D-2 receptor using radiol...	1535660
D(2) dopamine receptor	Ki	=	113.0	nM	6.95	Binding affinity to dopamine receptor D2	1573641
D(2) dopamine receptor	IC50	=	127.0	nM	6.9	DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone)	-
Serotonin 3 (5-HT3) receptor	Ki	=	158.49	nM	6.8	Tested for its binding affinity by measuring its ability to displace [3H]granise...	-
Serotonin 3 (5-HT3) receptor	Ki	=	199.53	nM	6.7	Binding affinity to 5-hydroxytryptamine 3 receptor using [3H]GR-65630 as radioli...	2342053
Serotonin 3 receptor (5HT3)	Ki	=	200.0	nM	6.7	Compound was evaluated for the binding affinity at 5- HT3 receptor subtype	7608898
D(3) dopamine receptor	IC50	=	200.0	nM	6.7	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Serotonin 3 (5-HT3) receptor	Ki	=	210.0	nM	6.68	Inhibition of [3H]GR-65630 binding to rat cortical membrane serotonin 5-hydroxyt...	12593651

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	187
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	67
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
3397992	10.1021/jm00403a011	Canis familiaris	13
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
3397992	10.1021/jm00403a011	Mustela putorius furo	10
28671460	10.1021/acs.jmedchem.7b00285	Myeloperoxidase	10
20070106	10.1021/jm901371v	Homo sapiens	8
2918518	10.1021/jm00123a033	Canis familiaris	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
1995885	10.1021/jm00106a023	Canis familiaris	5
12061889	10.1021/jm0200409	ADMET	5
21474681	10.1124/dmd.111.038778	Brain	5
2139471	10.1021/jm00167a020	Rattus norvegicus	5
1312602	10.1021/jm00083a014	Mustela putorius furo	4
3397992	10.1021/jm00403a011	D(2) dopamine receptor	4
6134832	10.1021/jm00361a022	Rattus norvegicus	4
18426954	10.1124/dmd.108.020479	ADMET	4

Data from ChEMBL 36 via Core Engine