Compound Detail

CHEMBL19019

NALTREXONE

💊 Approved Drug

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💊 Approved Drug

O=C1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL19019
Name	NALTREXONE
Phase	Approved
Structure Type	MOL
InChI Key	DQCKKXVULJGBQN-XFWGSAIBSA-N
Therapeutic	✓ Yes

Known Names

Celupan EN-1639A FREE BASE EN-1639A [AS HYDROCHLORIDE] Naltrexona Naltrexone NSC-758439 Trexal Vivitrol

Targets

320

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

341.4

MW (Da)

1.53

ALogP

HBA

HBD

70.0

PSA (Å²)

0.85

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1984
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	nal-
USAN Year	1973

Extended Properties

Molecular Formula	C20H23NO4
MW	341.41
Aromatic Rings	1
Heavy Atoms	25
NP-Likeness	1.72

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Opioid receptors; mu/kappa/delta antagonist	ANTAGONIST	Opioid receptors; mu/kappa/delta	✓	✓

Indications

Alcoholism Alcoholism Amphetamine-Related Disorders Borderline Personality Disorder Chronic Pain Cocaine-Related Disorders Cocaine-Related Disorders Depressive Disorder Endometriosis Gambling Heroin Dependence HIV Infections Multiple Sclerosis Obesity Opioid-Related Disorders Opioid-Related Disorders Pain Stress Disorders, Post-Traumatic Substance-Related Disorders Tobacco Use Disorder

ATC Classification

N07BB04

naltrexone

Level 1: NERVOUS SYSTEM

Level 2: OTHER NERVOUS SYSTEM DRUGS

Drug Warnings

Black Box Warning

General Warning

Country: United States

Activity Summary

Ki 234 meas. best 10.7

IC50 63 meas. best 9.7

EC50 18 meas. best 9.8

Kd 5 meas. best 10.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Opioid receptors; mu & delta CHEMBL2095149	Ki	10.7	10.7	0.0	1
Opioid receptors; delta & kappa CHEMBL2095151	Ki	10.4	10.4	0.0	1
Kappa-type opioid receptor CHEMBL237	Ki	10.38	9.0293	0.0	28
Mu-type opioid receptor CHEMBL233	Kd	10.3	10.3	0.1	1
Mu-type opioid receptor CHEMBL233	Ki	10.15	9.4115	0.1	40
Mu-type opioid receptor CHEMBL233	EC50	9.8	9.0625	0.2	4
Mu-type opioid receptor CHEMBL2858	EC50	9.8	9.8	0.2	2
Mu-type opioid receptor CHEMBL4354	Ki	9.77	9.2712	0.2	25
Mu-type opioid receptor CHEMBL4354	IC50	9.7	9.405	0.2	4
Mu-type opioid receptor CHEMBL2858	Ki	9.58	9.2678	0.3	9
Kappa-type opioid receptor CHEMBL3952	Ki	9.51	8.5682	0.3	38
Unchecked CHEMBL612545	Ki	9.43	8.052	0.4	10
Mu-type opioid receptor CHEMBL270	Ki	9.34	8.8833	0.5	15
Opioid receptor CHEMBL2094129	IC50	9.3	8.505	0.5	4
Kappa-type opioid receptor CHEMBL3952	IC50	9.3	8.3129	0.5	7
Opioid receptor CHEMBL2094129	EC50	9.3	9.3	0.5	1
Opioid receptor CHEMBL2094129	Ki	9.26	9.26	0.6	1
Mu-type opioid receptor CHEMBL233	IC50	9.23	8.2569	0.6	13
Unchecked CHEMBL612545	EC50	9.2	8.95	0.6	2
Kappa-type opioid receptor CHEMBL237	EC50	9.09	8.7667	0.8	3
Kappa-type opioid receptor CHEMBL4329	EC50	9.09	9.09	0.8	1
Opioid receptors; mu and delta CHEMBL2221343	Ki	9.06	9.06	0.9	1
Unchecked CHEMBL612545	IC50	9.02	8.63	0.9	2
Kappa-type opioid receptor CHEMBL3614	Ki	8.97	8.4975	1.1	4
Kappa-type opioid receptor CHEMBL4329	Ki	8.84	8.84	1.4	2
Mu-type opioid receptor CHEMBL270	IC50	8.82	8.46	1.5	3
Delta-type opioid receptor CHEMBL236	Kd	8.8	8.8	1.6	1
Mu-type opioid receptor CHEMBL2858	Kd	8.76	8.76	1.7	1
Kappa-type opioid receptor CHEMBL237	IC50	8.73	7.5175	1.9	4
Opioid receptors; mu & kappa CHEMBL2095156	IC50	8.59	8.255	2.6	2
Opioid receptors; mu/kappa/delta CHEMBL2095181	IC50	8.42	8.33	3.8	4
Delta-type opioid receptor CHEMBL3222	EC50	8.36	8.36	4.4	1
Delta-type opioid receptor CHEMBL236	EC50	8.36	8.14	4.4	4
Delta-type opioid receptor CHEMBL269	Ki	8.32	7.5589	4.8	9
Delta-type opioid receptor CHEMBL236	IC50	8.26	7.6271	5.4	7
Delta-type opioid receptor CHEMBL269	IC50	8.25	7.455	5.6	2
Delta-type opioid receptor CHEMBL236	Ki	8.2	7.6098	6.3	45
Mu-type opioid receptor CHEMBL2858	IC50	8.18	8.085	6.6	2
Delta-type opioid receptor CHEMBL3222	Ki	7.91	7.238	12.3	5
Kappa-type opioid receptor CHEMBL4329	Kd	7.74	7.74	18.2	1
Delta-type opioid receptor CHEMBL3222	Kd	7.41	7.41	38.9	1
Cavia porcellus CHEMBL369	IC50	7.3	7.3	50.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.0	6.0	1000.0	1
Neuronal acetylcholine receptor subunit alpha-7 CHEMBL2492	IC50	4.6	4.56	25000.0	2
Neuronal acetylcholine receptor subunit alpha-4 CHEMBL307	IC50	4.51	4.51	31000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	48.0	mL.min-1.kg-1	Homo sapiens
CL	57.0	mL.min-1.kg-1	Homo sapiens
CL	66.0	mL.min-1.kg-1	Macaca
CL	80.0	mL.min-1.kg-1	Rattus norvegicus
CL	90.0	mL.min-1.kg-1	Canis lupus familiaris
F	49.0	%	Homo sapiens
F	20.0	%	Homo sapiens
Fu	0.79	-	Homo sapiens
Ke	32.0	nM	-
Ke	1.0	nM	Cavia porcellus
Ke	5.5	nM	Cavia porcellus
Ke	1.2	nM	Cavia porcellus
Ke	5.5	nM	Cavia porcellus
Ke	37.0	nM	Cavia porcellus
Ke	43.0	nM	-
Ke	69.0	nM	-
Ke	0.38	nM	Cavia porcellus
Ke	5.5	nM	Cavia porcellus
Ke	1.0	nM	Cavia porcellus
Ke	24.0	nM	Cavia porcellus
Ke	32.0	-	-
Ke	1.0	-	Cavia porcellus
Ke	5.5	-	Cavia porcellus
Ke	0.2	nM	Cavia porcellus
Ke	0.21	nM	Mus musculus
Ke	5.5	nM	Cavia porcellus
Ke	1.0	nM	Cavia porcellus
Ke	24.4	nM	Mus musculus
Ke	0.93	nM	Cavia porcellus
Ke	19.3	nM	Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Opioid receptors; mu & delta	Ki	=	0.02	nM	10.7	Ratio of mu/delta-opioid receptors Binding affinity	12825957
Opioid receptors; delta & kappa	Ki	=	0.04	nM	10.4	Ratio of kappa/delta-opioid receptors Binding affinity	12825957
Kappa-type opioid receptor	Ki	=	0.042	nM	10.38	Antagonist activity at kappa opioid receptor expressed in HEK293 cells assessed ...	19683449
Mu-type opioid receptor	Kd	=	0.05012	nM	10.3	Activity at human mu opioid receptor by [35S]GTPgammaS binding assay	18298057
Mu-type opioid receptor	Ki	=	0.07	nM	10.15	Displacement of [125I]-IBOxyA from MOR-1 expressed in CHO cells	21621410
Mu-type opioid receptor	Ki	=	0.11	nM	9.96	Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells	19027293
Mu-type opioid receptor	Ki	=	0.11	nM	9.96	Binding affinity against Opioid receptor mu 1 expressed in CHO cells using [3H]D...	15808478
Mu-type opioid receptor	Ki	=	0.11	nM	9.96	Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells a...	19282177
Mu-type opioid receptor	EC50	=	0.16	nM	9.8	Stimulation of mouse MOR expressed in CHO cells after 1.5 hrs by [35S]GTPgammaS ...	25783191
Mu-type opioid receptor	Ki	=	0.1585	nM	9.8	Displacement of [3H]-DPN from recombinant human mu opioid receptor expressed in ...	31857840
Mu-type opioid receptor	EC50	=	0.16	nM	9.8	Displacement of [35S]GTP-gammaS from MOR (unknown origin)	38156970
Mu-type opioid receptor	EC50	=	0.16	nM	9.8	Agonist activity at mouse mu opioid receptor expressed in CHO cells assessed as ...	23948248
Mu-type opioid receptor	Ki	=	0.17	nM	9.77	Binding affinity towards Opioid receptor mu 1 of guinea pig brain membranes usin...	11425545
Mu-type opioid receptor	Ki	=	0.17	nM	9.77	Binding affinity was determined towards opioid receptor mu1 using [3H]DAMGO as r...	12749896
Kappa-type opioid receptor	Ki	=	0.19	nM	9.72	Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cel...	19027293
Kappa-type opioid receptor	Ki	=	0.19	nM	9.72	Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce...	19282177
Kappa-type opioid receptor	Ki	=	0.19	nM	9.72	Binding affinity against Opioid receptor kappa 1 expressed in CHO cells using [3...	15808478
Mu-type opioid receptor	Ki	=	0.2	nM	9.7	Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells	19253983
Mu-type opioid receptor	Ki	=	0.2	nM	9.7	Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in...	17004724
Mu-type opioid receptor	Ki	=	0.2	nM	9.7	Displacement of [3H]DAMGO from human cloned mu opioid receptor	17887741

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15920768	10.1002/jps.20373	ADMET	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
8627605	10.1021/jm950807f	Delta-type opioid receptor	6
28288109	10.1038/nchembio.2334	Mas-related G-protein coupled receptor member X2	6
38810170	10.1021/acs.jmedchem.4c00333	Mu-type opioid receptor	6
1851846	10.1021/jm00109a027	Mu-type opioid receptor	5
1851846	10.1021/jm00109a027	Kappa-type opioid receptor	5
8627605	10.1021/jm950807f	Kappa-type opioid receptor	5
19282177	10.1016/j.bmcl.2009.02.078	Delta-type opioid receptor	5
31857840	10.1021/acsmedchemlett.9b00406	Mus musculus	5
2160538	10.1021/jm00168a028	Kappa-type opioid receptor	5
2160538	10.1021/jm00168a028	Mu-type opioid receptor	5
2160538	10.1021/jm00168a028	Delta-type opioid receptor	5
19282177	10.1016/j.bmcl.2009.02.078	Kappa-type opioid receptor	5
19282177	10.1016/j.bmcl.2009.02.078	Mu-type opioid receptor	5
17407276	10.1021/jm061327z	Mu-type opioid receptor	4
17962026	10.1016/j.bmc.2007.10.030	Mus musculus	4

Data from ChEMBL 36 via Core Engine