◎ Sugi Atlas

Atlas / Drug / Methylnaltrexone

Methylnaltrexone

drug
On this page

Also known as Methylnaltrexone cationMethylnaltrexone ionMRZ-2663Methyl naltrexoneMETHYLNALTREXONE BROMIDEMethylnaltrexone (Bromide)

Summary

Methylnaltrexone (CHEMBL1186579) is an approved small molecule targeting OPRD1, OPRK1, and OPRM1; indicated across 9 conditions including constipation disorder and ileus.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • Targets: 3 (OPRD1, OPRK1, OPRM1)
  • Indications: 9 conditions
  • Clinical trials: 35
  • Chemistry: 356.4 Da · C21H26NO4+

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1186579
NameMethylnaltrexone
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID5361918
Molecular formulaC21H26NO4+
Molecular weight356.4
InChIKeyJVLBPIPGETUEET-GAAHOAFPSA-O

SMILES: C[N+]1(CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)CC6CC6

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

Also known as: Methylnaltrexone, Methylnaltrexone cation, Methylnaltrexone ion, MRZ-2663, Methyl naltrexone, METHYLNALTREXONE, methylnaltrexone, METHYLNALTREXONE BROMIDE, Methylnaltrexone (Bromide)

Parent form; salt/anhydrous children: CHEMBL470617, CHEMBL1201770

Patent coverage: 793 distinct patent families (3,390 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,369 (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 receptorAntagonist6.050.2%P41143
OPRK1κ receptorAntagonist8.20%P41145
OPRM1μ receptorAntagonist8.70%P35372

Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Mu-type opioid receptor, Delta-type opioid receptor, Kappa-type opioid receptor, Kappa-type opioid receptor.

Bioactivity

ChEMBL activities: 8 potent at pChembl ≥ 5 of 8 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
OPRM18.26Ki5.5nMCHEMBL_ACT_24423929
OPRK18.17EC506.7nMCHEMBL_ACT_25611564
OPRM18.1Ki7.94nMCHEMBL_ACT_18101570
OPRM18Ki10nMCHEMBL_ACT_25611559
P411447.7Ki19.95nMCHEMBL_ACT_18101640
OPRK17.49Ki32.1nMCHEMBL_ACT_24424075
OPRD16.3Ki501.2nMCHEMBL_ACT_18101605
OPRD15.46Ki3454nMCHEMBL_ACT_24424074

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

8 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)PhaseMONDOEFO
constipation disorder3MONDO:0002203HP:0002019
ileus3MONDO:0004567MONDO:0004567
gastroparesis2MONDO:0006769EFO:1000948
acute pancreatitis2MONDO:0006515EFO:1000652
opiate dependence1MONDO:0005530EFO:0005611
kidney disorder1MONDO:0005240EFO:0003086
liver disorder1MONDO:0005154HP:0001410
intestinal obstruction1MONDO:0004565MONDO:0004565

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

Clinical trials

Total trials: 35.

Phase distribution

PhaseTrials
PHASE410
PHASE19
PHASE36
PHASE24
PHASE2/PHASE33
Not specified3

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06162377PHASE4RECRUITINGMethylnatrexone In Resectable Head and Neck Squamous Cell Carcinoma (MINK). A Window of Opportunity Pilot Study.
NCT00672139PHASE4COMPLETEDSafety of Subcutaneous Methylnaltrexone for Opioid-Induced Constipation in Patients With Advanced Illness
NCT00672477PHASE4COMPLETEDStudy Evaluating Subcutaneous Methylnaltrexone For Treatment Of Opioid-Induced Constipation In Patients With Advanced Illness
NCT00858754PHASE4WITHDRAWNStudy Evaluating Safety & Efficacy of Subcutaneous Methylnaltrexone on Opioid-Induced Constipation in Cancer Subjects
NCT01012960PHASE4COMPLETEDOpioids and Esophageal Function
NCT01055704PHASE4COMPLETEDEffect of Methylnaltrexone on GI Transit in Healthy Volunteers
NCT01773096PHASE4COMPLETEDMethylnaltrexone Use for Opioid-induced Postoperative Constipation
NCT02403830PHASE4COMPLETEDEffect of Methylnaltrexone on the PK/PD Profiles of Ticagrelor in Patients Treated With Morphine
NCT02977286PHASE4TERMINATEDNaloxegol to Prevent Lower Gastrointestinal Paralysis in Critically Ill Adults Administered Opioids
NCT03523520PHASE4COMPLETEDMethylnaltrexone vs Naloxegol in the Treatment of Opioid-Induced Constipation
NCT00387309PHASE3COMPLETEDStudy Evaluating IV Methylnaltrexone for the Treatment of Post Operative Ileus
NCT00401375PHASE3COMPLETEDStudy of Intravenous (IV) Methylnaltrexone Bromide (MNTX) in the Treatment of Post-Operative Ileus (POI)
NCT00936884PHASE3COMPLETEDStudy Evaluating the Efficacy and Safety of Subcutaneous Methylnaltrexone (MOA-728) for the Treatment of Opioid-Induced-Constipation
NCT01050595PHASE3UNKNOWNMethylnaltrexone for Treatment of Opiate-Induced Constipation in the Intensive Care Unit
NCT01186770PHASE3COMPLETEDA Study of Oral Methylnaltrexone (MNTX) for the Treatment of Opioid-Induced Constipation (OIC) in Participants With Chronic, Non-Malignant Pain
NCT01360372PHASE3WITHDRAWNEffect of Methylnaltrexone (Relistor) on Digestion and Tolerance to Tube Feeding in Patients Treated With Opiates
NCT02574819PHASE2/PHASE3UNKNOWNStudy of Methylnaltrexone in Opioid-Induced Constipation Patients
NCT04083651PHASE2/PHASE3WITHDRAWNA Study of Methylnaltrexone Bromide (MNTX) in Participants With Advanced Pancreatic Cancer
NCT04743570PHASE2/PHASE3COMPLETEDEffects of Peripherally Acting µ-opioid Receptor Antagonists on Acute Pancreatitis
NCT00640146PHASE2COMPLETEDStudy of Subcutaneous Methylnaltrexone (MNTX) in the Treatment of Opioid-Induced Constipation During Rehabilitation After Orthopedic Procedures
NCT01004393PHASE2COMPLETEDMethylnaltrexone for Opioid-induced Constipation in Cancer Patients
NCT01117376PHASE2TERMINATEDMethylnaltrexone vs Erythromycin for Facilitating Gastric Emptying Time in Critically Ill Patients
NCT03852524PHASE2COMPLETEDSubcutaneous Methylnaltrexone Versus Placebo for Postoperative Ileus Prevention
NCT01363323PHASE1COMPLETEDEffect of Methylnaltrexone (MNTX) on Electrocardiogram (ECG) Parameters and Cardiac Repolarization
NCT01366326PHASE1COMPLETEDEvaluate the Pharmacokinetics (PK) of Methylnaltrexone (MNTX) in Healthy Adult Subjects
NCT01366339PHASE1COMPLETEDTolerance and Pharmacokinetics Study of MNTX Tablets
NCT01366365PHASE1COMPLETEDStudy of Pharmacokinetics, Safety and Tolerability of Intravenous Methylnaltrexone Bromide
NCT01366378PHASE1COMPLETEDEffect of Cimetidine on the Single-Dose PK of IV- Administered MNTX
NCT01367509PHASE1COMPLETEDPharmacokinetics, Safety, and Tolerability of Methylnaltrexone (MNTX) in Subjects With Impaired Renal Function
NCT01596764PHASE1COMPLETEDEffects of Methylnaltrexone in Comparison to Naloxone on Loperamide-induced Delay of the Oro-cecal, Whole-gut and Colon Transit Time.
NCT01596777PHASE1COMPLETEDEffects of 500 mg Immediate Release and Extended Release Methylnaltrexone on Loperamide-induced Delay of the Oro-cecal and Whole-gut Transit Time in Healthy Subjects
NCT01889290PHASE1COMPLETEDMethylnaltrexone Pharmacokinetics in Neurointensive Care Patients
NCT01368562Not specifiedCOMPLETEDCompassionate Use Study of Methylnaltrexone
NCT01955213Not specifiedTERMINATEDMethylnaltrexone for Opioid Induced Constipation
NCT03014843Not specifiedCOMPLETEDThe Effect of Naloxone and Methylnaltrexone on Esophageal Sensitivity in Health

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

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.

611 molecules share ≥1 primary target. Top 100 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
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
NALTREXONEChEMBLPhase 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
CP-866087ChEMBLPhase 2OPRD1, OPRK1, OPRM1
CYCLAZOCINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
DIPRENORPHINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
ETORPHINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
FLUNARIZINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
METAZOCINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
NALORPHINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
NIGULDIPINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
PENFLURIDOLChEMBLPhase 2OPRD1, OPRK1, OPRM1
SPIRADOLINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
AfatinibPubChemApprovedOPRD1, OPRK1, OPRM1
ApixabanPubChemApprovedOPRD1, OPRK1, OPRM1
BosentanPubChemApprovedOPRD1, OPRK1, OPRM1
FidaxomicinPubChemApprovedOPRD1, OPRK1, OPRM1
FulvestrantPubChemApprovedOPRD1, OPRK1, OPRM1
LinagliptinPubChemApprovedOPRD1, OPRK1, OPRM1
PyrazinamidePubChemApprovedOPRD1, OPRK1, OPRM1
saxagliptinPubChemApprovedOPRD1, OPRK1, OPRM1
TadalafilPubChemApprovedOPRD1, OPRK1, OPRM1
ALOGLIPTINChEMBL + PubChemPhase 4 (approved)OPRK1, OPRM1
EluxadolineChEMBL + PubChemPhase 4 (approved)OPRD1, OPRM1
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)OPRK1, OPRM1
MavorixaforChEMBL + PubChemPhase 4 (approved)OPRK1, OPRM1
REGORAFENIBChEMBL + PubChemPhase 4 (approved)OPRD1, OPRM1
ALFENTANILChEMBLPhase 4 (approved)OPRD1, OPRM1
ALPIDEMChEMBLPhase 4 (approved)OPRK1, OPRM1
AMBENONIUMChEMBLPhase 4 (approved)OPRK1, OPRM1
AMITRIPTYLINEChEMBLPhase 4 (approved)OPRK1, OPRM1
AMSACRINEChEMBLPhase 4 (approved)OPRD1, OPRK1
ARIPIPRAZOLEChEMBLPhase 4 (approved)OPRK1, OPRM1
ATOMOXETINEChEMBLPhase 4 (approved)OPRK1, OPRM1
BAZEDOXIFENEChEMBLPhase 4 (approved)OPRD1, OPRM1
BEPRIDILChEMBLPhase 4 (approved)OPRK1, OPRM1
BOSUTINIBChEMBLPhase 4 (approved)OPRK1, OPRM1
BROMOCRIPTINEChEMBLPhase 4 (approved)OPRK1, OPRM1
BROMPERIDOLChEMBLPhase 4 (approved)OPRK1, OPRM1
CALCITRIOLChEMBLPhase 4 (approved)OPRD1, OPRK1
CARVEDILOLChEMBLPhase 4 (approved)OPRK1, OPRM1
CHLORHEXIDINEChEMBLPhase 4 (approved)OPRK1, OPRM1
CINACALCETChEMBLPhase 4 (approved)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
Atlas version
v1.1.4
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot