Compounds > iperoxo
Page last updated: 2024-11-12

iperoxo

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

Description

iperoxo: a muscarinic M2 receptor agonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10104167
CHEMBL ID3121473
MeSH IDM000598130

Synonyms (7)

Synonym
bdbm50448377
4-(4,5-dihydro-1,2-oxazol-3-yloxy)but-2-ynyl-trimethylazanium
gtpl6937
iperoxo
CHEMBL3121473 ,
[4-(2-isoxazoline-3-yloxy)-2-butynyl]trimethylaminium
Q27078089

Research Excerpts

Overview

Iperoxo is an extremely potent muscarinic receptor agonist.

ExcerptReferenceRelevance
"Iperoxo is an extremely potent muscarinic receptor agonist."( Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor.
Dallanoce, C; De Amici, M; Holzgrabe, U; Klöckner, J; Kostenis, E; Mohr, K; Racké, K; Schrage, R; Seemann, WK, 2013)		1.11
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)IC50 (µMol)0.00130.00052.773925.1700AID1524444
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)IC50 (µMol)0.00130.00052.891925.1700AID1524444
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)IC50 (µMol)0.00130.00052.747825.1700AID1524444
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)IC50 (µMol)0.00130.00052.780225.1700AID1524444
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)IC50 (µMol)0.00130.00053.314249.5000AID1524444
Muscarinic acetylcholine receptor M1Homo sapiens (human)IC50 (µMol)0.00130.00001.403910.0000AID1524444
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Muscarinic acetylcholine receptor M1Homo sapiens (human)EC50 (µMol)0.00200.00161.304310.0000AID1199331
Muscarinic acetylcholine receptor M1Homo sapiens (human)Kd2.13800.00090.98292.6915AID1199333
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
positive regulation of monoatomic ion transportMuscarinic acetylcholine receptor M1Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
neuromuscular synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of locomotionMuscarinic acetylcholine receptor M1Homo sapiens (human)
saliva secretionMuscarinic acetylcholine receptor M1Homo sapiens (human)
cognitionMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of postsynaptic membrane potentialMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of glial cell proliferationMuscarinic acetylcholine receptor M1Homo sapiens (human)
positive regulation of intracellular protein transportMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
postsynaptic modulation of chemical synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
plasma membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
presynaptic membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
axon terminusMuscarinic acetylcholine receptor M1Homo sapiens (human)
Schaffer collateral - CA1 synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
postsynaptic density membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
glutamatergic synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
cholinergic synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M1Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1072459Toxicity in Swiss mouse assessed as lachrymation at 0.001 mg/kg, sc2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072499Agonist activity at muscarinic M3 receptor in albino guinea pig ileum assessed as stimulation of electrically-induced response2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1199332Partial agonist activity at human muscarinic M1 acetylcholine receptor expressed in CHO cells assessed as increase in IP1 accumulation incubated for 30 mins by FRET based HTRF assay relative to 100 uM acetylcholine2015Journal of medicinal chemistry, Jan-22, Volume: 58, Issue:2
Rational design of partial agonists for the muscarinic m1 acetylcholine receptor.
AID1072492Inhibition of acetylcholinesterase in rat brain homogenate at 100 uM after 15 mins by Ellman assay2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072471Toxicity in Swiss mouse assessed as diarrhea at 0.001 mg/kg, sc2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1199348Partial agonist activity at human muscarinic M1 acetylcholine receptor expressed in CHO cells assessed as increase in IP1 accumulation at 100 uM incubated for 30 mins in presence of 1 uM Gq protein inhibitor UBO-QIC by FRET based HTRF assay2015Journal of medicinal chemistry, Jan-22, Volume: 58, Issue:2
Rational design of partial agonists for the muscarinic m1 acetylcholine receptor.
AID1072465Toxicity in Swiss mouse assessed as salivation at 0.001 mg/kg, sc2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1199331Partial agonist activity at human muscarinic M1 acetylcholine receptor expressed in CHO cells assessed as increase in IP1 accumulation incubated for 30 mins by FRET based HTRF assay2015Journal of medicinal chemistry, Jan-22, Volume: 58, Issue:2
Rational design of partial agonists for the muscarinic m1 acetylcholine receptor.
AID1072501Agonist activity at muscarinic M1 receptor in New Zealand rabbit vas deferens assessed as stimulation of electrically-induced response2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072496Intrinsic activity at muscarinic M3 receptor in albino guinea pig ileum assessed as stimulation of electrically-induced response relative to bethanechol2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072453Toxicity in Swiss mouse assessed as hypothermia at 0.001 mg/kg, sc2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072485Sedative activity in sc dosed Swiss mouse assessed as immobility time at 0.01 mg/kg, sc by open-field test2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1524444Agonist activity at human muscarinic M1 receptor expressed in HEK293T cells co-expressing Galpha subunit and PLC-beta3 by split luciferase complementation assay2019Journal of medicinal chemistry, 03-28, Volume: 62, Issue:6
Fluorination of Photoswitchable Muscarinic Agonists Tunes Receptor Pharmacology and Photochromic Properties.
AID1199347Partial agonist activity at human muscarinic M1 acetylcholine receptor expressed in CHO cells assessed as increase in IP1 accumulation at 100 uM incubated for 30 mins in presence of 100 ng/ml Gi protein inhibitor PTX by FRET based HTRF assay2015Journal of medicinal chemistry, Jan-22, Volume: 58, Issue:2
Rational design of partial agonists for the muscarinic m1 acetylcholine receptor.
AID1072498Intrinsic activity at muscarinic M1 receptor in New Zealand rabbit vas deferens assessed as stimulation of electrically-induced response relative to McN-A-3432014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072491Antinociceptive activity in sc dosed Swiss mouse assessed as effect on acetic acid-induced writhing compound administered 30 mins prior challenge2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1524445Agonist activity at human muscarinic M1 receptor expressed in HEK293T cells co-expressing Galpha subunit and PLC-beta3 by split luciferase complementation assay relative to 100 uM carbachol2019Journal of medicinal chemistry, 03-28, Volume: 62, Issue:6
Fluorination of Photoswitchable Muscarinic Agonists Tunes Receptor Pharmacology and Photochromic Properties.
AID1072475Antinociceptive activity in Swiss mouse assessed as effect on acetic acid-induced writhing at 0.001 mg/kg, sc administered 30 mins prior challenge2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072500Agonist activity at muscarinic M2 receptor in albino guinea pig left atrium assessed as stimulation of electrically-induced response2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1072497Intrinsic activity at muscarinic M2 receptor in albino guinea pig left atrium assessed as stimulation of electrically-induced response relative to bethanechol2014European journal of medicinal chemistry, Mar-21, Volume: 75Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.
AID1199333Displacement of [3H]NMS from human muscarinic M1 acetylcholine receptor expressed in CHO cell membranes by radioligand binding assay2015Journal of medicinal chemistry, Jan-22, Volume: 58, Issue:2
Rational design of partial agonists for the muscarinic m1 acetylcholine receptor.
AID1345326Human M2 receptor (Acetylcholine receptors (muscarinic))2013British journal of pharmacology, May, Volume: 169, Issue:2
Agonists with supraphysiological efficacy at the muscarinic M2 ACh receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's13 (76.47)24.3611
2020's4 (23.53)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.80

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.80 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index3.00 (0.95)

This Compound (24.80)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
arecoline
Arecoline: An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.. arecoline : A tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine.		2.1310enoate ester;
methyl ester;
pyridine alkaloid;
tetrahydropyridine		metabolite;
muscarinic agonist
azobenzene
azobenzene: photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength; RN given refers to cpd without isomeric designation; structure. (E)-azobenzene : The (E)-isomer of azobenzene.. (Z)-azobenzene : The (Z)-isomer of azobenzene.. azobenzene : A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds.		2.2110azobenzenes
bethanechol
Bethanechol: A slowly hydrolyzing muscarinic agonist with no nicotinic effects. Bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, HEART RATE changes, and BRONCHIAL SPASM.. bethanechol : The carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention.		2.110carbamate ester;
quaternary ammonium ion		muscarinic agonist
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		2.1710maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
oxotremorine
Oxotremorine: A non-hydrolyzed muscarinic agonist used as a research tool.		2.3110N-alkylpyrrolidine
carbachol
Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.		2.8830ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic
pilocarpine
Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.		2.930pilocarpineantiglaucoma drug
(4-(m-chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium chloride
(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride: A drug that selectively activates certain subclasses of muscarinic receptors and also activates postganglionic nicotinic receptors. It is commonly used experimentally to distinguish muscarinic receptor subtypes.		2.5920
isoxazoles
Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.		4.09130isoxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.2110diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
xanomeline
xanomeline: a cholinergic agonist; used in the treatment of Alzheimer's disease; structure given in first source		2.7220tetrahydropyridine;
thiadiazoles		muscarinic agonist;
serotonergic agonist
n-methylscopolamine
N-Methylscopolamine: A muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors.		2.5220
w 84
[no description available]		2.110
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.1510
1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid: has been shown to exhibit unprecedented positive allosteric activity for ACh binding as well as inherent agonist activity at the M1 muscarinic receptor; structure in first source		2.1110
ConditionIndicatedRelationship StrengthStudiesTrials