Compound Detail

CHEMBL841

LOPERAMIDE

💊 Approved Drug

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💊 Approved Drug

CN(C)C(=O)C(CCN1CCC(O)(c2ccc(Cl)cc2)CC1)(c1ccccc1)c1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL841
Name	LOPERAMIDE
Phase	Approved
Structure Type	MOL
InChI Key	RDOIQAHITMMDAJ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Loperamida Loperamide

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

477.1

MW (Da)

5.09

ALogP

HBA

HBD

43.8

PSA (Å²)

0.52

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1976
Availability	OTC
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Year

1975

Extended Properties

Molecular Formula	C29H33ClN2O2
MW	477.05
Aromatic Rings	3
Heavy Atoms	34
NP-Likeness	-0.36

Indications

Carcinoma, Non-Small-Cell Lung Diarrhea Fecal Incontinence Breast Neoplasms Breast Neoplasms Breast Neoplasms Clostridium Infections Eczema Neoplasms Paget Disease, Extramammary Intestinal Obstruction Pain

ATC Classification

A07DA03

loperamide

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS

A07DA53

loperamide, combinations

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS

Activity Summary

IC50 33 meas. best 8.84

Ki 23 meas. best 9.8

EC50 9 meas. best 7.24

Kd 2 meas. best 5.46

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mu-type opioid receptor CHEMBL270	Ki	9.8	9.8	0.2	1
Mu-type opioid receptor CHEMBL233	Ki	9.57	9.36	0.3	3
Mu-type opioid receptor CHEMBL233	IC50	8.84	8.84	1.4	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	7.48	7.48	33.0	1
Delta-type opioid receptor CHEMBL269	Ki	7.3	7.3	50.1	1
Mu-type opioid receptor CHEMBL4354	EC50	7.24	7.24	58.0	1
Unchecked CHEMBL612545	Ki	7.07	6.5225	85.0	4
Unchecked CHEMBL612545	IC50	7.03	6.448	93.0	5
Delta-type opioid receptor CHEMBL236	EC50	6.81	6.81	156.0	1
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	6.62	6.62	239.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.58	6.58	264.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	6.57	6.57	270.0	1
Delta-type opioid receptor CHEMBL236	Ki	6.5	6.5	316.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.34	6.025	454.0	2
Cavia porcellus CHEMBL369	EC50	6.31	6.31	488.9	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.27	6.27	534.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	6.2	6.2	628.0	1
Unchecked CHEMBL612545	EC50	6.16	6.16	685.0	1
Delta-type opioid receptor CHEMBL236	IC50	6.05	6.05	896.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.01	6.01	965.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	5.93	5.93	1170.0	1
Kappa-type opioid receptor CHEMBL237	Ki	5.9	5.9	1250.0	1
D(3) dopamine receptor CHEMBL234	IC50	5.87	5.87	1337.0	1
Cocaine esterase CHEMBL3180	Ki	5.82	5.82	1500.0	1
D(4) dopamine receptor CHEMBL219	Ki	5.73	5.73	1850.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.7	5.7	2000.0	1
Beta-2 adrenergic receptor CHEMBL210	Ki	5.68	5.68	2066.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.66	5.66	2202.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	5.6	5.6	2517.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.6	5.6	2500.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.58	5.58	2613.0	1
Histamine H2 receptor CHEMBL1941	Ki	5.52	5.52	3030.0	1
Beta-2 adrenergic receptor CHEMBL210	IC50	5.52	5.52	3005.0	1
Trypanosoma cruzi CHEMBL368	EC50	5.52	5.52	3000.0	1
Histamine H2 receptor CHEMBL1941	IC50	5.51	5.51	3081.0	1
Kappa-type opioid receptor CHEMBL237	IC50	5.5	5.5	3125.0	1
Calmodulin CHEMBL6092	Kd	5.46	5.46	3500.0	1
Human coronavirus 229E CHEMBL613837	EC50	5.4	5.4	4000.0	1
Cocaine esterase CHEMBL3180	IC50	5.39	5.3	4060.0	3
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.39	5.39	4105.0	1
Middle East respiratory syndrome-related coronavirus CHEMBL4296578	EC50	5.32	5.32	4800.0	1
D(2) dopamine receptor CHEMBL217	Ki	5.24	5.24	5790.0	1
Angiopoietin-1 receptor CHEMBL4128	Kd	5.23	5.23	5900.0	1
SARS-CoV CHEMBL4303836	EC50	5.23	5.23	5900.0	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	5.21	5.21	6219.0	1
SARS-CoV-2 CHEMBL4303835	IC50	5.03	4.85	9270.0	3
Calmodulin CHEMBL6092	IC50	4.92	4.92	12000.0	1
ADMET CHEMBL612558	EC50	4.92	4.92	12000.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.62	4.62	23700.0	1
Somatostatin receptor type 5 CHEMBL1792	IC50	4.48	4.48	33110.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	184.0	ng.hr.mL-1	Rattus norvegicus
AUC	651.0	ng.hr.mL-1	Rattus norvegicus
AUC	1020.0	ng.hr.mL-1	Rattus norvegicus
AUC	980.0	ng.hr.mL-1	Rattus norvegicus
AUC	806.0	ng.hr.mL-1	Rattus norvegicus
AUC	122.0	ng.hr.mL-1	Rattus norvegicus
AUC	161.0	ng.hr.mL-1	Rattus norvegicus
AUC	243.0	ng.hr.mL-1	Rattus norvegicus
AUC	131.0	ng.hr.mL-1	Rattus norvegicus
AUC	4.433	ng.hr.mL-1	Mus musculus
AUC	4.483	ng.hr.mL-1	Mus musculus
AUC	81.67	ng.hr.mL-1	Mus musculus
AUC	1.5	ng.hr.mL-1	Mus musculus
AUC	7.0	ng.hr.mL-1	Mus musculus
AUC	95.0	ng.hr.mL-1	Mus musculus
AUC	0.9333	ng.hr.mL-1	Mus musculus
AUC	0.5167	ng.hr.mL-1	Mus musculus
AUC	1.033	ng.hr.mL-1	Mus musculus
AUC	4.333	ng.hr.mL-1	Mus musculus
CL	13.8	uL.min-1.(10^6cells)-1	Homo sapiens
CL	45.71	mL.min-1.g-1	Homo sapiens
CL	91.2	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	166.67	mL.min-1.kg-1	Rattus norvegicus
CL	110.0	mL.min-1.kg-1	Rattus norvegicus
CL	75.0	mL.min-1.kg-1	Rattus norvegicus
CL	128.33	mL.min-1.kg-1	Rattus norvegicus
Cmax	125.77	nM	Rattus norvegicus
Cmax	144.64	nM	Rattus norvegicus
Cmax	473.74	nM	Rattus norvegicus
Cmax	188.66	nM	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mu-type opioid receptor	Ki	=	0.16	nM	9.8	Binding affinity for Mu opioid receptor of rat brain	15456245
Mu-type opioid receptor	Ki	=	0.268	nM	9.57	Displacement of [3H]DAMGO from human mu opioid receptor expressed in HEK293 cell...	34011153
Mu-type opioid receptor	Ki	=	0.53	nM	9.28	Binding affinity for recombinant human mu-opioid receptor was determined by usin...	15454210
Mu-type opioid receptor	Ki	=	0.586	nM	9.23	DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine...	-
Mu-type opioid receptor	IC50	=	1.445	nM	8.84	DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine...	-
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	33.0	nM	7.48	Inhibition of human ERG expressed in HEK293 cells at holding potential of -80 mV...	29274816
Delta-type opioid receptor	Ki	=	50.1	nM	7.3	Binding affinity for delta opioid receptor of rat brain	15456245
Mu-type opioid receptor	EC50	=	58.0	nM	7.24	Inhibition of mu opioid receptor mediated GTPgammaS binding to CHO cell membrane...	15456245
Unchecked	Ki	=	85.0	nM	7.07	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-
Unchecked	IC50	=	93.0	nM	7.03	DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox...	-
Delta-type opioid receptor	EC50	=	156.0	nM	6.81	Inhibition of delta opioid receptor mediated GTPgammaS binding to CHO cell membr...	15456245
Unchecked	Ki	=	196.0	nM	6.71	DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:...	-
Unchecked	IC50	=	221.0	nM	6.66	DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:...	-
Sodium channel protein type 5 subunit alpha	IC50	=	239.0	nM	6.62	Inhibition of human Nav1.5 channel expressed in HEK293 cells at holding potentia...	29274816
Sigma non-opioid intracellular receptor 1	Ki	=	264.0	nM	6.58	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Sodium channel alpha subunits; brain (Types I, II, III)	IC50	=	270.0	nM	6.57	Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol...	2579237
Delta-type opioid receptor	Ki	=	316.0	nM	6.5	DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindo...	-
Unchecked	IC50	=	350.0	nM	6.46	Inhibition of human CES2A using fluorescein diacetate as fluorescent substrate p...	37544184
D(3) dopamine receptor	Ki	=	454.0	nM	6.34	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
Cavia porcellus	EC50	=	488.9	nM	6.31	Inhibition of isolated guinea pig ileum contraction induced by electrical stimul...	15857121

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	411
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	55
22711747	10.1124/dmd.112.046508	Rattus norvegicus	43
31732255	10.1016/j.ejmech.2019.111813	ADMET	19
23288866	10.1124/dmd.112.049965	Mus musculus	18
3906127	10.1021/jm00149a013	Rattus norvegicus	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18024584	10.1073/pnas.0709695104	H4	13
27173385	10.1016/j.ejmech.2016.04.058	Plasmodium falciparum	11
21051535	10.1124/dmd.110.034629	ADMET	9
27173385	10.1016/j.ejmech.2016.04.058	Unchecked	6
-	10.6019/CHEMBL3301361	ADMET	6
27173385	10.1016/j.ejmech.2016.04.058	Chloroquine resistance transporter	5
23288866	10.1124/dmd.112.049965	Intestine	5
11602674	-	ATP-dependent translocase ABCB1	5
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
23288866	10.1124/dmd.112.049965	ADMET	4
21149540	10.1124/dmd.110.035998	Brain	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4

Data from ChEMBL 36 via Core Engine