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 78.09 49.02 22 106 34352 2323605

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

Pharmacologic Action:

SourceCodeDescription
ATC A06AH01 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR CONSTIPATION
DRUGS FOR CONSTIPATION
Peripheral opioid receptor antagonists
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
FDA EPC N0000175691 Opioid Antagonist
FDA MoA N0000000154 Opioid Antagonists
FDA CS M0474216 Quaternary Ammonium Compounds

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
12MG/0.6ML (12MG/0.6ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 10376584 April 8, 2024 TREATMENT OF OPIOID-INDUCED CONSTIPATION
8MG/0.4ML (8MG/0.4ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 10376584 April 8, 2024 TREATMENT OF OPIOID-INDUCED CONSTIPATION
12MG/0.6ML (12MG/0.6ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 8420663 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
12MG/0.6ML (12MG/0.6ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 8822490 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
12MG/0.6ML (12MG/0.6ML) RELISTOR SALIX PHARMS N021964 April 24, 2008 RX SOLUTION SUBCUTANEOUS 9180125 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
12MG/0.6ML (12MG/0.6ML) RELISTOR SALIX PHARMS N021964 April 24, 2008 RX SOLUTION SUBCUTANEOUS 9492445 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
8MG/0.4ML (8MG/0.4ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 8420663 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
8MG/0.4ML (8MG/0.4ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 8822490 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
8MG/0.4ML (8MG/0.4ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 9180125 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
8MG/0.4ML (8MG/0.4ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 9492445 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
150MG RELISTOR SALIX N208271 July 19, 2016 RX TABLET ORAL 8420663 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
150MG RELISTOR SALIX N208271 July 19, 2016 RX TABLET ORAL 9180125 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
150MG RELISTOR SALIX N208271 July 19, 2016 RX TABLET ORAL 9492445 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
150MG RELISTOR SALIX N208271 July 19, 2016 RX TABLET ORAL 9724343 Sept. 30, 2029 TREATMENT OF OPIOID-INDUCED CONSTIPATION
12MG/0.6ML (12MG/0.6ML) RELISTOR SALIX PHARMS N021964 April 24, 2008 RX SOLUTION SUBCUTANEOUS 8247425 Dec. 31, 2030 TREATMENT OF OPIOID-INDUCED CONSTIPATION
8MG/0.4ML (8MG/0.4ML) RELISTOR SALIX PHARMS N021964 Sept. 27, 2010 RX SOLUTION SUBCUTANEOUS 8247425 Dec. 31, 2030 TREATMENT OF OPIOID-INDUCED CONSTIPATION

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
C2343585 UMLSCUI
CHEMBL1186579 ChEMBL_ID
RFO6IL3D3M UNII
8728 INN_ID
916055-92-0 SECONDARY_CAS_RN
DB06800 DRUGBANK_ID
CHEBI:136007 CHEBI
CHEMBL1201770 ChEMBL_ID
5361918 PUBCHEM_CID
7563 IUPHAR_LIGAND_ID
C032257 MESH_SUPPLEMENTAL_RECORD_UI
429838001 SNOMEDCT_US
d07135 MMSL
29899 RXNORM
4027431 VANDF
431072004 SNOMEDCT_US
012677 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Relistor HUMAN PRESCRIPTION DRUG LABEL 1 65649-150 TABLET 150 mg ORAL NDA 18 sections
Relistor HUMAN PRESCRIPTION DRUG LABEL 1 65649-551 INJECTION, SOLUTION 12 mg SUBCUTANEOUS NDA 18 sections
Relistor HUMAN PRESCRIPTION DRUG LABEL 1 65649-552 INJECTION, SOLUTION 8 mg SUBCUTANEOUS NDA 18 sections