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Naltrexone

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Also known as CelupanEN-1639A FREE BASEEN-1639A [AS HYDROCHLORIDE]NaltrexonaNSC-758439TrexalVivitrolSID170465207SID144205560NA(+)-Naltrexone

Summary

Naltrexone (CHEMBL19019) is an approved small-molecule μ-opioid receptor antagonist (ATC N07BB04) targeting OPRD1, OPRK1, and OPRM1; indicated across 53 conditions including alcohol abuse and pathological gambling.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N07BB04
  • Targets: 3 (OPRD1, OPRK1, OPRM1)
  • Indications: 53 conditions
  • Clinical trials: 280
  • Chemistry: 341.4 Da · C20H23NO4

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL19019
NameNaltrexone
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID5360515
ChEBICHEBI:7465
ATCN07BB04
Molecular formulaC20H23NO4
Molecular weight341.4
InChIKeyDQCKKXVULJGBQN-XFWGSAIBSA-N

SMILES: C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O

IUPAC name: (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

ChEBI definition: An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A μ-opioid receptor antagonist, it is used to treat alcohol dependence.

Pharmacological roles (ChEBI): μ-opioid receptor antagonist, central nervous system depressant, antidote to opioid poisoning.

Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.

Also known as: Celupan, EN-1639A FREE BASE, EN-1639A [AS HYDROCHLORIDE], Naltrexona, Naltrexone, NSC-758439, Trexal, Vivitrol, naltrexone, NALTREXONE, SID170465207, SID144205560

Parent form; salt/anhydrous children: CHEMBL1201149, CHEMBL4303313

Patent coverage: 8,926 distinct patent families (34,647 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 34,257 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
OPRD1δ receptorAntagonist80.2%P41143
OPRK1κ receptorAntagonist9.40%P41145
OPRM1μ receptorAntagonist9.70%P35372

Broader ChEMBL bioactivity targets: 20 (assay-derived). Sample: Opioid receptor, Opioid receptors; mu & delta, Opioid receptors; delta & kappa, Opioid receptors; mu & kappa, Opioid receptors; mu/kappa/delta, Opioid receptors; mu and delta, Mu-type opioid receptor, Delta-type opioid receptor, Kappa-type opioid receptor, Neuronal acetylcholine receptor subunit alpha-7.

Bioactivity

ChEMBL activities: 304 potent at pChembl ≥ 5 of 307 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
OPRM110.7Ki0.02nMCHEMBL_ACT_642017
OPRD110.4Ki0.04nMCHEMBL_ACT_642016
OPRK110.38Ki0.04nMCHEMBL_ACT_3070137
OPRM110.3Kd0.05nMCHEMBL_ACT_2115991
OPRM110.15Ki0.07nMCHEMBL_ACT_6262900
OPRM19.96Ki0.11nMCHEMBL_ACT_1519220
OPRM19.96Ki0.11nMCHEMBL_ACT_2263763
OPRM19.96Ki0.11nMCHEMBL_ACT_2407516
P428669.8EC500.16nMCHEMBL_ACT_13417668
P428669.8EC500.16nMCHEMBL_ACT_15172128
OPRM19.8Ki0.16nMCHEMBL_ACT_19291436
OPRM19.8EC500.16nMCHEMBL_ACT_25943333
P972669.77Ki0.17nMCHEMBL_ACT_152201
P972669.77Ki0.17nMCHEMBL_ACT_399760
OPRK19.72Ki0.19nMCHEMBL_ACT_1519222
OPRK19.72Ki0.19nMCHEMBL_ACT_2263765
OPRK19.72Ki0.19nMCHEMBL_ACT_2407479
OPRM19.7Ki0.2nMCHEMBL_ACT_1470060
OPRM19.7Ki0.2nMCHEMBL_ACT_14997950
OPRM19.7Ki0.2nMCHEMBL_ACT_16427814
OPRM19.7Ki0.2nMCHEMBL_ACT_1759534
OPRM19.7Ki0.2nMCHEMBL_ACT_1774660
OPRM19.7Ki0.2nMCHEMBL_ACT_1928210
OPRM19.7Ki0.2nMCHEMBL_ACT_2606064
OPRM19.7Ki0.2nMCHEMBL_ACT_501822
OPRM19.7Ki0.2nMCHEMBL_ACT_642015
P972669.7IC500.2nMCHEMBL_ACT_769193
OPRM19.64Ki0.23nMCHEMBL_ACT_1859779
P972669.64IC500.23nMCHEMBL_ACT_354430
OPRK19.6Ki0.25nMCHEMBL_ACT_1859787

Target pathways

Aggregated over 3 target gene(s): OPRD1, OPRK1, OPRM1.

Top Reactome pathways

6 total, by targets touching each:

PathwayTargetsGenes
Peptide ligand-binding receptors3OPRD1, OPRK1, OPRM1
G alpha (i) signalling events3OPRD1, OPRK1, OPRM1
Interleukin-4 and Interleukin-13 signaling2OPRD1, OPRM1
MECP2 regulates neuronal receptors and channels2OPRK1, OPRM1
Opioid Signalling1OPRM1
G-protein activation1OPRM1

Dominant GO biological processes

GO termTargets
G protein-coupled receptor signaling pathway3
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway3
phospholipase C-activating G protein-coupled receptor signaling pathway3
neuropeptide signaling pathway3
G protein-coupled opioid receptor signaling pathway3
signal transduction3
immune response2
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger2
response to nicotine2
eating behavior2
response to ethanol2
sensory perception2
sensory perception of pain2
adult locomotory behavior1
negative regulation of gene expression1

Indications & clinical

Indications

53 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
alcohol abuse4MONDO:0002046MONDO:0002046
pathological gambling3MONDO:0011662EFO:0004699
opiate dependence3MONDO:0005530EFO:0005611
HIV infectious disease3MONDO:0005109EFO:0000764
obesity disorder3MONDO:0011122EFO:0001073
methamphetamine dependence3MONDO:0005419EFO:0004701
heroin dependence3MONDO:0005367EFO:0004240
nicotine dependence3MONDO:0008575EFO:0003768
cocaine dependence3MONDO:0005186EFO:0002610
drug dependence3MONDO:0005303EFO:0003890
post-traumatic stress disorder3MONDO:0005146EFO:0001358
borderline personality disorder3MONDO:0001156HP:0012076
endometriosis3MONDO:0005133EFO:0001065
depressive disorder3MONDO:0002050MONDO:0002050
multiple sclerosis3MONDO:0005301MONDO:0005301
Crohn disease2MONDO:0005011EFO:0000384
obsessive-compulsive disorder2MONDO:0008114EFO:0004242
ulcerative colitis2MONDO:0005101EFO:0000729
cannabis dependence2MONDO:0005689EFO:0007191
dry eye syndrome2MONDO:0006733EFO:1000906
severe acute respiratory syndrome2MONDO:0005091EFO:0000694
fibromyalgia2MONDO:0005546EFO:0005687
acute respiratory distress syndrome2MONDO:0006502EFO:1000637
major depressive disorder2MONDO:0002009MONDO:0002009
breast neoplasm2MONDO:0021100MONDO:0007254
alcohol-related disorders2MONDO:0021698MONDO:0021698
interstitial cystitis2MONDO:0018301EFO:0008507
diabetic neuropathy2MONDO:0006626EFO:1000783
migraine disorder2MONDO:0005277MONDO:0005277
trichotillomania2MONDO:0013189MONDO:0013189
long COVID-192MONDO:0100233MONDO:0100233
atopic eczema1MONDO:0004980EFO:0000274
psoriasis1MONDO:0005083EFO:0000676
pervasive developmental disorder1MONDO:0000594MONDO:0000594
mental disorder1MONDO:0005084EFO:0000677
melanoma1MONDO:0005105EFO:0000756
binge eating disorder0MONDO:0005582EFO:0005924
bulimia nervosa0MONDO:0005452EFO:0005204
anorexia nervosa0MONDO:0005351MONDO:0005351

14 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 280.

Phase distribution

PhaseTrials
PHASE290
PHASE465
PHASE332
PHASE130
Not specified27
PHASE2/PHASE319
PHASE1/PHASE29
EARLY_PHASE18

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06426303PHASE4RECRUITINGSex Differences in Trauma, Inflammation and Brain Function and the Implications for Treatment Efficacy in Alcohol Use Disorder
NCT06620562PHASE4RECRUITINGImproving Efficacity of Sleeve Gastrectomy With Naltrexone/Bupropion Extended-release Tablet
NCT07213466PHASE4RECRUITINGIndividualized Pharmacological Approach to Obesity in Patients With Bipolar Disorder
NCT00000438PHASE4COMPLETEDNaltrexone Treatment for Alcoholism
NCT00000442PHASE4COMPLETEDNaltrexone for Relapse Prevention
NCT00000445PHASE4COMPLETEDUse of Naltrexone in a Clinical Setting
NCT00000447PHASE4COMPLETEDBehavioral/Drug Therapy for Alcohol-Nicotine Dependence (Naltrexone/Nicotine Patch)
NCT00000448PHASE4COMPLETEDNaltrexone Treatment for Alcoholic Women
NCT00000449PHASE4COMPLETEDBehavior and Naltrexone Treatment for Alcoholics
NCT00000450PHASE4COMPLETEDNaltrexone Maintenance Treatment of Alcoholism
NCT00000452PHASE4COMPLETEDNaltrexone Treatment of Alcohol Dependence
NCT00000455PHASE4COMPLETEDNaltrexone for Early Problem Drinkers
NCT00000456PHASE4COMPLETEDBehavioral Therapy Plus Naltrexone for Alcoholism
NCT00004554PHASE4COMPLETEDSertraline for Alcohol Dependence and Depression
NCT00006203PHASE4COMPLETEDNaltrexone, Craving, and Drinking
NCT00006204PHASE4COMPLETEDDrug Treatment for Depressed Alcoholics (Naltrexone/Fluoxetine)
NCT00006449PHASE4COMPLETEDPost-Treatment Effects of Naltrexone
NCT00006489PHASE4COMPLETEDTreatment for Alcoholism and Post-Traumatic Stress Disorder (Naltrexone)
NCT00018824PHASE4COMPLETEDTreating Alcohol Use In Older Adults With Depression
NCT00115037PHASE4COMPLETEDManaging Alcoholism in People Who Do Not Respond to Naltrexone
NCT00120601PHASE4UNKNOWNTrial for the Treatment of Alcohol Dependence
NCT00223275PHASE4COMPLETEDNaltrexone for Bipolar Disorder and Alcohol Dependence
NCT00256451PHASE4COMPLETEDEndophenotype for Alcohol Misuse in Healthy Minority Populations
NCT00366626PHASE4COMPLETEDEffectiveness of Naltrexone Versus Placebo to Reduce Craving for Alcohol With Evaluation of Genetic Variability.
NCT00369408PHASE4COMPLETEDTargeted Naltrexone for Problem Drinkers
NCT00453804PHASE4COMPLETEDInjectable Versus Oral Naltrexone Treatment of Alcohol Dependence In Serious Mental Illness (SMI)
NCT00461890PHASE4TERMINATEDLong-Acting Injectable Naltrexone Treatment of Alcohol Dependence in Primary Care vs. in Specialized Chemical Dependence Treatment: A Pilot Trial
NCT00511836PHASE4COMPLETEDALK21-018: Effects of Medisorb® Naltrexone (VIVITROL®) on Alcohol Craving in Treatment-seeking, Alcohol-dependent Adults
NCT00568958PHASE4COMPLETEDNaltrexone for Heavy Drinking in Young Adults
NCT00817089PHASE4COMPLETEDUnderstanding Treatment Response With Naltrexone Among White Alcoholics
NCT00831272PHASE4COMPLETEDPharmacogenetic Response to Naltrexone For Alcohol Dependence
NCT00854230PHASE4WITHDRAWNPharmacotherapy for HIV Infected Patients With Alcohol Problems
NCT00920829PHASE4COMPLETEDGenetic and Brain Mechanisms of Naltrexone’s Treatment Efficacy for Alcoholism
NCT01015066PHASE4WITHDRAWNComparison of Buprenorphine/Naloxone With Naltrexone in Opioid Dependent Adolescents
NCT01052831PHASE4COMPLETEDNaltrexone for Impulse Control Disorders in Parkinson’s Disease
NCT01155869PHASE4TERMINATEDPilot Study of Depot NTX in Homeless Veterans
NCT01377168PHASE4COMPLETEDNaltrexone for Medication Compliance Among HIV-infected Men With Alcohol Use Disorder
NCT01453374PHASE4COMPLETEDA Study of VIVITROL in the Prevention of Re-arrest and Re-incarceration
NCT01471145PHASE4COMPLETEDDepot Naltrexone Mechanism of Action in Heroin Dependent Patients Using fMRI and SPECT
NCT01528007PHASE4COMPLETEDTreatment of Pathological Gambling With Naltrexone Pharmacotherapy and Brief Intervention

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of CPIC Guideline for alfentanil, buprenorphine, codeine, fCPICCOMT;OPRM1

PharmGKB also curates 10 clinical and 52 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

612 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DihydroergotamineChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
PROPOXYPHENEChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
TAFAMIDISChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
ALVIMOPANChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMIODARONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMLODIPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMOXAPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ASTEMIZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BENZTROPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BUPRENORPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BUTORPHANOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CANNABIDIOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CHLORPROMAZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CINNARIZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CLOTRIMAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CODEINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ECONAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FENTANYLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FLUPHENAZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FLUSPIRILENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
HYDROCODONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
HYDROMORPHONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LANSOPRAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LEVORPHANOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LOPERAMIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LOXAPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MEPERIDINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
METHADONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
METHYLNALTREXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MICONAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MORPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NAFTOPIDILChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALBUPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALFURAFINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALMEFENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALOXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NELFINAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OLICERIDINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OXYCODONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OXYMORPHONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PAROXETINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PASIREOTIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PENTAZOCINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PIMOZIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
RALOXIFENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
RITONAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SAMIDORPHANChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SAQUINAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SUNITINIBChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
TAMOXIFENChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
TRAMADOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ASIMADOLINEChEMBLPhase 3OPRD1, OPRK1, OPRM1
ATICAPRANTChEMBLPhase 3OPRD1, OPRK1, OPRM1
CEBRANOPADOLChEMBLPhase 3OPRD1, OPRK1, OPRM1
NAVACAPRANTChEMBLPhase 3OPRD1, OPRK1, OPRM1
TRIMEBUTINEChEMBLPhase 3OPRD1, OPRK1, OPRM1
BREMAZOCINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
CARFENTANILChEMBLPhase 2OPRD1, OPRK1, OPRM1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
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Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot