U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26NO4.Br
Molecular Weight 436.339
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLNALTREXONE BROMIDE

SMILES

[Br-].[H][C@]12OC3=C4C(C[C@]5([H])[C@](O)(CCC1=O)[C@]24CC[N@+]5(C)CC6CC6)=CC=C3O

InChI

InChIKey=IFGIYSGOEZJNBE-NQMNLMSRSA-N
InChI=1S/C21H25NO4.BrH/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13;/h4-5,12,16,19,25H,2-3,6-11H2,1H3;1H/t16-,19+,20+,21-,22-;/m1./s1

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H25NO4
Molecular Weight 355.4275
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 4 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Methylnaltrexone, is a peripherally acting μ-opioid receptor antagonist that acts on the gastrointestinal tract to inhibit the opioid-induced decrease in gastric motility and transit time. It is used to treat opiate-induced constipation in adults with chronic non-cancer pain and in adults with advanced illness who are receiving palliative care.

CNS Activity

Curator's Comment: Methylnaltrexone is a quaternary ammonium derivate of naltrexone with higher polarity, lower lipid solubility and therefore less ability to pass the blood brain barrier

Originator

Curator's Comment: Methylnaltrexone was developed at the University of Chicago, USA, and out-licensed to UR Labs in 1985.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
RELISTOR

Approved Use

RELISTOR is an opioid antagonist indicated for: Treatment of opioid-induced constipation (OIC) in adult patients with chronic non‑cancer pain (1.1) Treatment of opioid-induced constipation in patients with advanced illness who are receiving palliative care, when response to laxative therapy has not been sufficient. Limitation of Use: Use beyond four months has not been studied (1.2) 1.1 Opioid-Induced Constipation in Adult Patients with Chronic Non-Cancer Pain RELISTOR is indicated for the treatment of opioid-induced constipation in adult patients with chronic non‑cancer pain. 1.2 Opioid-Induced Constipation in Adult Patients with Advanced Illness RELISTOR is indicated for the treatment of opioid-induced constipation in adult patients with advanced illness who are receiving palliative care, when response to laxative therapy has not been sufficient. Limitation of Use Use of RELISTOR beyond four months has not been studied in the advanced illness population.

Launch Date

1.20899515E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
538 ng/mL
0.3 mg/kg single, intravenous
dose: 0.3 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLNALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
224 ng × h/mL
0.3 mg/kg single, intravenous
dose: 0.3 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLNALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 h
0.3 mg/kg single, intravenous
dose: 0.3 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLNALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
0.3 mg/kg single, intravenous
dose: 0.3 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLNALTREXONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
0.5 mg/kg single, subcutaneous
Highest studied dose
healthy, 18-45
n = 119
450 mg 1 times / day multiple, oral
Recommended
Dose: 450 mg, 1 times / day
Route: oral
Route: multiple
Dose: 450 mg, 1 times / day
Sources: Page: p.144
unhealthy, 51.6
n = 200
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Age Group: 51.6
Sex: M+F
Population Size: 200
Sources: Page: p.144
Disc. AE: Vertigo...
AEs leading to
discontinuation/dose reduction:
Vertigo (0.5%)
Sources: Page: p.144
0.45 mg/kg 1 times / 6 hours multiple, intravenous
Highest studied dose
Dose: 0.45 mg/kg, 1 times / 6 hours
Route: intravenous
Route: multiple
Dose: 0.45 mg/kg, 1 times / 6 hours
Sources:
healthy
n = 8
0.64 mg/kg single, intravenous
Highest studied dose
Dose: 0.64 mg/kg
Route: intravenous
Route: single
Dose: 0.64 mg/kg
Sources: Page: p.17
healthy
12 mg 1 times / day multiple, subcutaneous
Recommended
Dose: 12 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 12 mg, 1 times / day
Sources: Page: p.9
unhealthy
n = 150
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Population Size: 150
Sources: Page: p.9
Disc. AE: Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (2%)
Sources: Page: p.9
12 mg 1 times / day multiple, subcutaneous
Recommended
Dose: 12 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 12 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Disc. AE: Gastrointestinal perforation, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal perforation
Diarrhea (severe)
Opiate withdrawal symptoms
Sources: Page: p.1
450 mg 1 times / day multiple, oral
Recommended
Dose: 450 mg, 1 times / day
Route: oral
Route: multiple
Dose: 450 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Disc. AE: Gastrointestinal perforation, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal perforation
Diarrhea (severe)
Opiate withdrawal symptoms
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Vertigo 0.5%
Disc. AE
450 mg 1 times / day multiple, oral
Recommended
Dose: 450 mg, 1 times / day
Route: oral
Route: multiple
Dose: 450 mg, 1 times / day
Sources: Page: p.144
unhealthy, 51.6
n = 200
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Age Group: 51.6
Sex: M+F
Population Size: 200
Sources: Page: p.144
Abdominal pain 2%
Disc. AE
12 mg 1 times / day multiple, subcutaneous
Recommended
Dose: 12 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 12 mg, 1 times / day
Sources: Page: p.9
unhealthy
n = 150
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Population Size: 150
Sources: Page: p.9
Gastrointestinal perforation Disc. AE
12 mg 1 times / day multiple, subcutaneous
Recommended
Dose: 12 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 12 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Opiate withdrawal symptoms Disc. AE
12 mg 1 times / day multiple, subcutaneous
Recommended
Dose: 12 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 12 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Diarrhea severe
Disc. AE
12 mg 1 times / day multiple, subcutaneous
Recommended
Dose: 12 mg, 1 times / day
Route: subcutaneous
Route: multiple
Dose: 12 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Gastrointestinal perforation Disc. AE
450 mg 1 times / day multiple, oral
Recommended
Dose: 450 mg, 1 times / day
Route: oral
Route: multiple
Dose: 450 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Opiate withdrawal symptoms Disc. AE
450 mg 1 times / day multiple, oral
Recommended
Dose: 450 mg, 1 times / day
Route: oral
Route: multiple
Dose: 450 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
Diarrhea severe
Disc. AE
450 mg 1 times / day multiple, oral
Recommended
Dose: 450 mg, 1 times / day
Route: oral
Route: multiple
Dose: 450 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Opioid-induced constipation in adults with chronic non-cancer pain
Sources: Page: p.1
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
not significant
unlikely [IC50 >10 uM]
unlikely [IC50 >10 uM]
unlikely [IC50 >10 uM]
unlikely [IC50 >10 uM]
unlikely [IC50 >100 uM]
unlikely [IC50 >25 uM]
weak
no (co-administration study)
Comment: injection of drug did not affect metabolism of dextromethorphan: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021964s019,208271s003lbl.pdf#page=9
Page: 7.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
yes
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Clinical status of methylnaltrexone, a new agent to prevent and manage opioid-induced side effects.
2004 Mar-Apr
Opioids and opioid receptors in the enteric nervous system: from a problem in opioid analgesia to a possible new prokinetic therapy in humans.
2004 May 6
Preclinical studies of opioids and opioid antagonists on gastrointestinal function.
2004 Oct
In vitro evaluation of the effect of the opioid antagonist N-methylnaltrexone on motility of the equine jejunum and pelvic flexure.
2005 Jul
Brain delta2 opioid receptors mediate SNC-80-evoked hypothermia in rats.
2005 Jul 5
Tolerability, gut effects, and pharmacokinetics of methylnaltrexone following repeated intravenous administration in humans.
2005 May
[(3)H]Alvimopan binding to the micro opioid receptor: comparative binding kinetics of opioid antagonists.
2005 Sep 27
Peripherally acting mu-opioid-receptor antagonists and the connection between postoperative ileus and pain management: The anesthesiologist's view and beyond.
2006 Apr
Methylnaltrexone inhibits opiate and VEGF-induced angiogenesis: role of receptor transactivation.
2006 Jul-Sep
Pharmacokinetics of the opioid antagonist N-methylnaltrexone and evaluation of its effects on gastrointestinal tract function in horses treated or not treated with morphine.
2006 Jun
Methylnaltrexone, a novel peripheral opioid receptor antagonist for the treatment of opioid side effects.
2006 May
Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus.
2007
Attenuation of vascular permeability by methylnaltrexone: role of mOP-R and S1P3 transactivation.
2007 Aug
Treatment of opioid-induced gut dysfunction.
2007 Feb
Reversal of opioid-induced bladder dysfunction by intravenous naloxone and methylnaltrexone.
2007 Jul
A review of methylnaltrexone, a peripheral opioid receptor antagonist, and its role in opioid-induced constipation.
2007 Jun
The in vitro pharmacology of the peripherally restricted opioid receptor antagonists, alvimopan, ADL 08-0011 and methylnaltrexone.
2007 May
Peripherally acting opioid antagonists in the treatment of opiate-related constipation: a systematic review.
2007 Nov
Emerging pharmacologic options for treating postoperative ileus.
2007 Oct 15
Opioid-induced constipation in intensive care patients: relief in sight?
2008
New approaches to the treatment of opioid-induced constipation.
2008 Aug
Methylnaltrexone (Relistor) for opioid induced constipation.
2008 Aug 11
Methylnaltrexone reduced opioid-induced constipation in patients with terminal illness.
2008 Dec
Reversal of opioid-induced gastric dysfunction in a critically ill burn patient after methylnaltrexone.
2008 Dec
Methylnaltrexone, a new peripheral mu-receptor antagonist for the prevention and treatment of opioid-induced extracerebral side effects.
2008 Jan
Managing opioid-induced constipation.
2008 Jul
Synergistic effects of methylnaltrexone with 5-fluorouracil and bevacizumab on inhibition of vascular endothelial growth factor-induced angiogenesis.
2008 Jun
Methylnaltrexone: a new treatment for an old problem.
2008 Nov
Development of peripheral opioid antagonists' new insights into opioid effects.
2008 Oct
Efficacy and safety of mu-opioid antagonists in the treatment of opioid-induced bowel dysfunction: systematic review and meta-analysis of randomized controlled trials.
2008 Sep
Methylnaltrexone, a new peripherally acting mu-opioid receptor antagonist being evaluated for the treatment of postoperative ileus.
2008 Sep
Methylnaltrexone for opioid-induced constipation in advanced illness.
2008 Sep 4
New drug update: 2008.
2009 Apr
Pharmacological management of postoperative ileus.
2009 Apr
Novel opioid antagonists for opioid-induced bowel dysfunction and postoperative ileus.
2009 Apr 4
Methylnaltrexone: new drug. Opiate-induced constipation: barely more effective than placebo.
2009 Aug
Methylnaltrexone, a peripherally acting opioid receptor antagonist, enhances tumoricidal effects of 5-Fu on human carcinoma cells.
2009 Aug
Protease inhibitor-induced nausea and vomiting is attenuated by a peripherally acting, opioid-receptor antagonist in a rat model.
2009 Aug 21
Methylnaltrexone.
2009 Jul
Methylnaltrexone reduced body weight gain in ob/ob mice.
2009 Jul-Aug
Preventing paralytic ileus: can the anesthesiologist help.
2009 Jun
Prokinetic drugs for feed intolerance in critical illness: current and potential therapies.
2009 Jun
Peripherally acting mu-opioid receptor antagonists and postoperative ileus: mechanisms of action and clinical applicability.
2009 Jun
Pharmacologic pearls for end-of-life care.
2009 Jun 15
Opioid receptors in the gastrointestinal tract.
2009 Jun 5
An overview of constipation and newer therapies.
2009 Jun-Jul
Detailing of gastrointestinal symptoms in cancer patients with advanced disease: new methodologies, new insights, and a proposed approach.
2009 Mar
Methylnaltrexone treatment of opioid-induced constipation in patients with advanced illness.
2009 Nov
[Methylnaltrexone. A new approach for therapy of opioid-induced obstipation].
2009 Oct
[Successful treatment of treatment-resistant opioid-induced constipation in a patient with incomplete paraplegia with methylnaltrexone].
2009 Oct
Patents

Sample Use Guides

Dosing For opioid-induced constipation (OIC) in adult patients with chronic non-cancer pain: tablets: The recommended dosage is 450 mg once daily in the morning. injection: The recommended dosage is 12 mg subcutaneously once daily. For OIC in adult patients with advanced illness: The pre-filled syringe is only for patients who require an injection dose of 8 mg or 12 mg. Administer one dose every other day, as needed, but no more frequently than one dose in a 24-hour period
Route of Administration: Other
There was tested the effect of methylnaltrexone on the action of 5-fluorouracil (5-FU) in three human cancer cell lines. Compared to 5-FU 10 muM alone on SW-480 cells (63.5+/-1.1%), on MCF-7 cells (58.3+/-3.1%), or on non-small cell lung cancer cells (81.3+/-1.6%), 5-FU 10 muM plus methylnaltrexone 1.0 muM reduced cancer cell growth in all three cell lines to 50.2+/-2.9% for SW-480 cells (p<0.05), 50.0+/-1.7% for MCF-7 cells (p<0.05) and 68.7+/-2.2% for lung cancer cells (p<0.01). Methylnaltrexone alone also showed anti-proliferative activity in the three cell lines. Methylnaltrexone at 1.0 muM, reduced SW-480 cell growth to 81.9+/-3.7% (p<0.01), MCF-7 cell growth to 85.9+/-2.4% (p<0.01) and lung cancer cell growth to 85.5+/-2.2% (p<0.01). Apoptosis was not induced by treatment of SW-480 cells with 1.0 or 10 muM methylnaltrexone for 48 h. However, methylnaltrexone increased the number of cells in the G(1)-phase and decreased the expression of cyclin A.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:33:54 UTC 2023
Edited
by admin
on Fri Dec 15 16:33:54 UTC 2023
Record UNII
RFO6IL3D3M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLNALTREXONE BROMIDE
DASH   EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
METHYLNALTREXONE BROMIDE [USAN]
Common Name English
Methylnaltrexone Bromide [WHO-DD]
Common Name English
methylnaltrexone bromide [INN]
Common Name English
MORPHINAN-17-IUM-6-ONE, 17-(CYCLOPROPYLMETHYL)-4,5-EPOXY-3,14-DIHYDROXY-17-METHYL-, BROMIDE, (5.ALPHA.,17R)-
Systematic Name English
METHYLNALTREXONE BROMIDE [ORANGE BOOK]
Common Name English
NALTREXONE METHOBROMIDE
Common Name English
METHYLNALTREXONE BROMIDE [EMA EPAR]
Common Name English
METHYLNALTREXONE BROMIDE [VANDF]
Common Name English
METHYLNALTREXONE BROMIDE [JAN]
Common Name English
MRZ-2663BR
Code English
MRZ2663BR
Code English
N-METHYLNALTREXONE BROMIDE
Common Name English
METHYLNALTREXONE BROMIDE [USP-RS]
Common Name English
MOA728
Code English
METHYLNALTREXONE BROMIDE [USP MONOGRAPH]
Common Name English
METHYLNALTREXONE BROMIDE [MI]
Common Name English
RELISTOR
Brand Name English
NALTREXONE METHYLBROMIDE
Common Name English
MOA-728
Code English
METHYLNALTREXONE BROMIDE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QA06AH01
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
EMA ASSESSMENT REPORTS RELISTOR (AUTHORIZED: OPIOID-RELATED DISEASES)
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
EMA ASSESSMENT REPORTS RELISTOR (AUTHORIZED: CONSTIPATION)
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
NCI_THESAURUS C681
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
WHO-ATC A06AH01
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
Code System Code Type Description
RXCUI
979111
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1430735
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
NCI_THESAURUS
C80569
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
MERCK INDEX
m7442
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY Merck Index
FDA UNII
RFO6IL3D3M
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
DRUG BANK
DBSALT000116
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
CAS
916055-92-0
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
SMS_ID
100000089659
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
DAILYMED
RFO6IL3D3M
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL1186579
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID30868236
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
USAN
RR-16
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
CAS
73232-52-7
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
EVMPD
SUB25787
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
PUBCHEM
16089914
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
INN
8728
Created by admin on Fri Dec 15 16:33:54 UTC 2023 , Edited by admin on Fri Dec 15 16:33:54 UTC 2023
PRIMARY
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