methylnaltrexone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
4616 83387-25-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • relistor
  • methylnaltrexone
  • methylnaltrexonium
  • methylnaltrexone bromide
a selective antagonist of opioid binding at the mu-opioid receptor with restricted ability to cross the blood-brain barrier, function as a peripherally-acting mu‑opioid receptor antagonist in tissues such as the gastrointestinal tract, thereby decreasing the constipating effects of opioids without impacting opioid-mediated analgesic effects on the central nervous system
  • Molecular weight: 356.44
  • Formula: C21H26NO4
  • CLOGP: -2.64
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 66.76
  • ALOGS: -4.73
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
6 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 52.75 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.34 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 2.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 22 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.87 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 2, 2008 EMA
April 24, 2008 FDA SALIX PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Abdominal pain 61.88 32.62 36 498 229995 46455533

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Death 39.22 32.33 31 286 357252 29594909

Pharmacologic Action:

SourceCodeDescription
ATC A06AH01 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR CONSTIPATION
DRUGS FOR CONSTIPATION
Peripheral opioid receptor antagonists
FDA CS M0474216 Quaternary Ammonium Compounds
FDA MoA N0000000154 Opioid Antagonists
FDA EPC N0000175691 Opioid Antagonist
MeSH PA D002491 Central Nervous System Agents
MeSH PA D009292 Narcotic Antagonists
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Therapeutic opioid induced constipation indication 136801000119102
Gastrointestinal ulcer contraindication 40845000
Gastrointestinal perforation contraindication 51875005
Acute nephropathy contraindication 58574008
Gastrointestinal obstruction contraindication 126765001
Chronic diarrhea contraindication 236071009
Primary malignant neoplasm of gastrointestinal tract contraindication 363745004
Macrocolon contraindication 367495003
Severe diarrhea contraindication 409587002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.26 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Mu-type opioid receptor GPCR ANTAGONIST Ki 7.55 WOMBAT-PK CHEMBL
Kappa-type opioid receptor GPCR Ki 6.65 WOMBAT-PK
Cytochrome P450 2D6 Enzyme Ki 5.10 WOMBAT-PK
Delta-type opioid receptor GPCR Ki 6.05 CHEMBL

External reference:

IDSource
D06618 KEGG_DRUG
916055-93-1 SECONDARY_CAS_RN
4027431 VANDF
4027432 VANDF
C0066411 UMLSCUI
CHEBI:136007 CHEBI
CHEMBL1186579 ChEMBL_ID
CHEMBL1201770 ChEMBL_ID
DB06800 DRUGBANK_ID
C032257 MESH_SUPPLEMENTAL_RECORD_UI
7563 IUPHAR_LIGAND_ID
8728 INN_ID
0RK7M7IABE UNII
5361918 PUBCHEM_CID
29899 RXNORM
136491 MMSL
25289 MMSL
d07135 MMSL
012677 NDDF
012678 NDDF
429838001 SNOMEDCT_US
431072004 SNOMEDCT_US
433519000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Relistor HUMAN PRESCRIPTION DRUG LABEL 1 65649-150 TABLET 150 mg ORAL NDA 28 sections
Relistor HUMAN PRESCRIPTION DRUG LABEL 1 65649-551 INJECTION, SOLUTION 12 mg SUBCUTANEOUS NDA 28 sections
Relistor HUMAN PRESCRIPTION DRUG LABEL 1 65649-552 INJECTION, SOLUTION 8 mg SUBCUTANEOUS NDA authorized generic 28 sections