Page last updated: 2024-12-11

n-methylnaltrindole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N-methylnaltrindole: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5362396
CHEMBL ID477154
SCHEMBL ID13633357
MeSH IDM0200864

Synonyms (13)

Synonym
n-methylnaltrindole
CHEMBL477154 ,
4,8-methanobenzofuro(2,3-a)pyrido(4,3-b)carbazole-1,8a(9h)-diol, 7-(cyclopropylmethyl)-5,6,7,8,14,14b-hexahydro-14-methyl-, (8r-(4bs*,8alpha,8abeta,14bbeta))-
unii-m993bkl35v
m993bkl35v ,
111555-57-8
4,8-methanobenzofuro(2,3-a)pyrido(4,3-b)carbazole-1,8a(9h)-diol, 7-(cyclopropylmethyl)-5,6,7,8,14,14b-hexahydro-14-methyl-, (4bs,8r,8as,14br)-)
SCHEMBL13633357
bdbm50451343
7-(cyclopropylmethyl)-14-methyl-5,6,7,8,14,14b-hexahydro-4,8-methano[1]benzofuro[2,3-a]pyrido[4,3-b]carbazole-1,8a(9h)-diol
DTXSID20912217
Q27283696
(1s,2s,13r,21r)-22-(cyclopropylmethyl)-11-methyl-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene-2,16-diol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorHomo sapiens (human)Ki0.00050.00000.59789.9300AID149921
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)Ki0.00830.00000.20186.4240AID149417
Mu-type opioid receptorCavia porcellus (domestic guinea pig)Ki0.03920.00000.27869.0000AID148051
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorMus musculus (house mouse)Ke0.00100.00010.14726.1080AID148810; AID148813
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)Ke0.02000.00000.03891.1570AID148835
Mu-type opioid receptorCavia porcellus (domestic guinea pig)Ke0.01100.00000.01590.0430AID150010
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
immune responseDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerDelta-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
adult locomotory behaviorDelta-type opioid receptorHomo sapiens (human)
negative regulation of gene expressionDelta-type opioid receptorHomo sapiens (human)
negative regulation of protein-containing complex assemblyDelta-type opioid receptorHomo sapiens (human)
positive regulation of CREB transcription factor activityDelta-type opioid receptorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationDelta-type opioid receptorHomo sapiens (human)
response to nicotineDelta-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayDelta-type opioid receptorHomo sapiens (human)
eating behaviorDelta-type opioid receptorHomo sapiens (human)
regulation of mitochondrial membrane potentialDelta-type opioid receptorHomo sapiens (human)
regulation of calcium ion transportDelta-type opioid receptorHomo sapiens (human)
cellular response to growth factor stimulusDelta-type opioid receptorHomo sapiens (human)
cellular response to hypoxiaDelta-type opioid receptorHomo sapiens (human)
cellular response to toxic substanceDelta-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayDelta-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
G protein-coupled opioid receptor activityDelta-type opioid receptorHomo sapiens (human)
protein bindingDelta-type opioid receptorHomo sapiens (human)
receptor serine/threonine kinase bindingDelta-type opioid receptorHomo sapiens (human)
G protein-coupled enkephalin receptor activityDelta-type opioid receptorHomo sapiens (human)
neuropeptide bindingDelta-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
plasma membraneDelta-type opioid receptorHomo sapiens (human)
synaptic vesicle membraneDelta-type opioid receptorHomo sapiens (human)
dendrite membraneDelta-type opioid receptorHomo sapiens (human)
presynaptic membraneDelta-type opioid receptorHomo sapiens (human)
axon terminusDelta-type opioid receptorHomo sapiens (human)
spine apparatusDelta-type opioid receptorHomo sapiens (human)
postsynaptic density membraneDelta-type opioid receptorHomo sapiens (human)
neuronal dense core vesicleDelta-type opioid receptorHomo sapiens (human)
plasma membraneDelta-type opioid receptorHomo sapiens (human)
neuron projectionDelta-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (44)

Assay IDTitleYearJournalArticle
AID147978Binding affinity was measured by the displacement of [3H]- EK in guinea pig brain membrane of opioid receptor kappa1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID147983Compound was evaluated for the binding affinity to opioid receptor kappa using [3H]-EK as radioligand in guinea pig brain membrane1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID148040Binding affinity was measured by the displacement of [3H]- DAMGO in guinea pig brain membrane of Opioid receptor mu 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID149872Opioid receptor mu 1 antagonistic activity was measured by the displacement of morphine in the guinea pig ileum at a concentration of 100 nM1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID227057Competitive inhibition of the DADLE on mouse vas deferens for the opioid receptor delta at 200 nM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID149002Antagonistic potency at opioid receptor mu (100 nM) (Ke =IC50 in the presence of antagonist divided by the control IC50 value)1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID365581Antitussive activity in ip dosed Sprague-Dawley rat assessed as reduction in number of capsaicin-induced coughs2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Structure-antitussive activity relationships of naltrindole derivatives. Identification of novel and potent antitussive agents.
AID149196Compound was evaluated for the binding affinity to opioid receptor delta using [3H]DADLE as radioligand in guinea pig brain membrane1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID147968Antagonistic potency at opioid receptor kappa (100 nM) (Ke =IC50 in the presence of antagonist divided by the control IC50 value)1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID149417Binding affinity to Opioid receptor kappa 1 by using [3H]U-69593 as a radioligand from guinea pig2001Bioorganic & medicinal chemistry letters, Apr-09, Volume: 11, Issue:7
Selective delta-opioid receptor ligands: potential PET ligands based on naltrindole.
AID148693Opioid receptor kappa 1 antagonistic activity was measured by the displacement of ethylketazocine in the guinea pig ileum at a concentration of 100 nM1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID147964Opioid receptor kappa antagonistic activity was measured by the displacement of ethylketazocine in the guinea pig ileum at a concentration of 100 nM1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID233705Selectivity ratio was determined from Ke value of Opioid receptor kappa 1 and Opioid receptor delta 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID148795Activity against Opioid receptor delta 1 on electrically stimulated mouse vas deferens using DADLE as agonist1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Pyrrolomorphinans as delta opioid receptor antagonists. The role of steric hindrance in conferring selectivity.
AID227049Competitive inhibition of Ethylketazocine on Guinea pig ileal longitudinal muscle for the opioid receptor kappa at 100 nM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID150010Antagonist potency was determined as the ratio of [antagonist] to (IC50 ratio-1) for Opioid receptor mu 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID233443Selectivity ratio measured as the delta IC50 to that of mu IC50 values.1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Pyrrolomorphinans as delta opioid receptor antagonists. The role of steric hindrance in conferring selectivity.
AID235328Selectivity ratio of kappa opioid receptor to delta opioid receptor1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Application of the message-address concept in the design of highly potent and selective non-peptide delta opioid receptor antagonists.
AID149208Opioid receptor delta antagonistic activity was measured by the displacement of DADLE in the mouse vas deferens at tha concentration of 200 nM1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID233878Selectivity ratio was determined from Ke value of Opioid receptor mu 1 and Opioid receptor delta 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID149011Binding affinity was measured by the displacement of [3H]- DAMGO in guinea pig brain membrane of opioid receptor mu1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID148998Opioid receptor mu antagonistic activity was measured by the displacement of morphine in the guinea pig ileum at a concentration of 100 nM1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID149213Antagonistic potency at opioid receptor delta (200 nM) (Ke =IC50 in the presence of antagonist divided by the control IC50 value)1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID148810Antagonist potency was determined as the ratio of [antagonist] to (IC50 ratio-1) for opioid receptor delta 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID149907Binding affinity was measured by the displacement of [3H]- DADLE in guinea pig brain membrane of Opioid receptor delta 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID148120Selectivity ratio is IC50 value of opioid receptor kappa to that of opioid receptor delta1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID233442Selectivity ratio measured as the delta IC50 to that of kappa IC50 values.1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Pyrrolomorphinans as delta opioid receptor antagonists. The role of steric hindrance in conferring selectivity.
AID148051Binding affinity to Opioid receptor mu 1 by using [3H]DAMGO as a radioligand from guinea pig2001Bioorganic & medicinal chemistry letters, Apr-09, Volume: 11, Issue:7
Selective delta-opioid receptor ligands: potential PET ligands based on naltrindole.
AID149161Selectivity ratio is IC50 value of mu-opioid receptor to that of delta-opioid receptor1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID149833Tested for the ratio of the binding affinities of Opioid receptor kappa 1/Opioid receptor delta 12001Bioorganic & medicinal chemistry letters, Apr-09, Volume: 11, Issue:7
Selective delta-opioid receptor ligands: potential PET ligands based on naltrindole.
AID148664Opioid receptor delta 1 antagonistic activity was measured by the displacement of DADLE in the mouse vas deferens at tha concentration of 200 nM1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID148187Tested for the ratio of the binding affinities of Opioid receptor mu 1/Opioid receptor delta 12001Bioorganic & medicinal chemistry letters, Apr-09, Volume: 11, Issue:7
Selective delta-opioid receptor ligands: potential PET ligands based on naltrindole.
AID148813Antagonistic activity against Opioid receptor delta 1 using [D-Ala2,D-Leu5]enkephalin in mouse vas deferens preparation1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Application of the message-address concept in the design of highly potent and selective non-peptide delta opioid receptor antagonists.
AID227052Competitive inhibition of Morphine on Guinea pig ileal longitudinal muscle for the opioid receptor mu at 100 nM1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
AID149921Binding affinity to Opioid receptor delta 1 using [3H]DPDPE as a radioligand in guinea pig2001Bioorganic & medicinal chemistry letters, Apr-09, Volume: 11, Issue:7
Selective delta-opioid receptor ligands: potential PET ligands based on naltrindole.
AID148836Antagonistic activity against Opioid receptor kappa 1 using ethylketazocine in guinea pig ileum preparation1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Application of the message-address concept in the design of highly potent and selective non-peptide delta opioid receptor antagonists.
AID150002Activity against mu receptor on electrically stimulated guinea pig ileum using morphine as the standard agonist (Opioid receptor mu 1)1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Pyrrolomorphinans as delta opioid receptor antagonists. The role of steric hindrance in conferring selectivity.
AID235331Selectivity ratio of mu opioid receptor to delta opioid receptor1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Application of the message-address concept in the design of highly potent and selective non-peptide delta opioid receptor antagonists.
AID148835Antagonist potency was determined as the ratio of [antagonist] to (IC50 ratio-1) for Opioid receptor kappa 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID149192Binding affinity was measured by the displacement of [3H]- DADLE in guinea pig brain membrane of opioid receptor delta1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID150012Antagonistic activity against Opioid receptor mu 1 using morphine in guinea pig ileum preparation1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Application of the message-address concept in the design of highly potent and selective non-peptide delta opioid receptor antagonists.
AID149279Binding affinity was measured by the displacement of [3H]- EK in guinea pig brain membrane of Opioid receptor kappa 11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Design of peptidomimetic delta opioid receptor antagonists using the message-address concept.
AID148830Activity against Opioid receptor kappa 1 on electrically stimulated guinea pig ileum using ethylketazocine as the standard agonist.1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Pyrrolomorphinans as delta opioid receptor antagonists. The role of steric hindrance in conferring selectivity.
AID149016Compound was evaluated for the binding affinity to Opioid receptor mu using [3H]DAMGO as radioligand in guinea pig brain membrane1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Role of spacer and address components in peptidomimetic delta opioid receptor antagonists related to naltrindole.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (9.09)18.7374
1990's6 (54.55)18.2507
2000's3 (27.27)29.6817
2010's0 (0.00)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.43

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.43 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.99 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (9.09%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]