Compounds > 3-hydroxymexiletine
Page last updated: 2024-12-10

3-hydroxymexiletine

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

Description

3-hydroxymexiletine: metabolite of mexiletine; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035569
CHEMBL ID2018453
SCHEMBL ID12486640
MeSH IDM0190224

Synonyms (14)

Synonym
3-hydroxymexiletine
3-(2-aminopropoxy)-2,4-dimethylphenol
bdbm50380408
rac-m-hydroxymexiletine
chembl2018453 ,
meta-hydroxymexiletine
phenol, 3(or 4)-(2-aminopropoxy)-2,4(or 3,5)-dimethyl-
1-(2,6-dimethyl-3-hydroxyphenoxy)-2-aminopropane
3(or 4)-(2-aminopropoxy)-2,4(or 3,5)-dimethylphenol
129417-37-4
m-hydroxymexiletine
SCHEMBL12486640
DTXSID20926399
PD189105
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium channel protein type 5 subunit alphaHomo sapiens (human)IC50 (µMol)102.00000.00033.64849.2000AID655925; AID655926
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
regulation of heart rateSodium channel protein type 5 subunit alphaHomo sapiens (human)
cardiac conduction system developmentSodium channel protein type 5 subunit alphaHomo sapiens (human)
cardiac ventricle developmentSodium channel protein type 5 subunit alphaHomo sapiens (human)
brainstem developmentSodium channel protein type 5 subunit alphaHomo sapiens (human)
sodium ion transportSodium channel protein type 5 subunit alphaHomo sapiens (human)
positive regulation of sodium ion transportSodium channel protein type 5 subunit alphaHomo sapiens (human)
response to denervation involved in regulation of muscle adaptationSodium channel protein type 5 subunit alphaHomo sapiens (human)
telencephalon developmentSodium channel protein type 5 subunit alphaHomo sapiens (human)
cerebellum developmentSodium channel protein type 5 subunit alphaHomo sapiens (human)
sodium ion transmembrane transportSodium channel protein type 5 subunit alphaHomo sapiens (human)
odontogenesis of dentin-containing toothSodium channel protein type 5 subunit alphaHomo sapiens (human)
positive regulation of action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
positive regulation of epithelial cell proliferationSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarizationSodium channel protein type 5 subunit alphaHomo sapiens (human)
cardiac muscle contractionSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of ventricular cardiac muscle cell membrane repolarizationSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of atrial cardiac muscle cell membrane depolarizationSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of atrial cardiac muscle cell membrane repolarizationSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of ventricular cardiac muscle cell membrane depolarizationSodium channel protein type 5 subunit alphaHomo sapiens (human)
cellular response to calcium ionSodium channel protein type 5 subunit alphaHomo sapiens (human)
cardiac muscle cell action potential involved in contractionSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of cardiac muscle cell contractionSodium channel protein type 5 subunit alphaHomo sapiens (human)
ventricular cardiac muscle cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during cardiac muscle cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
atrial cardiac muscle cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
SA node cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
AV node cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
bundle of His cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during AV node cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during SA node cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during Purkinje myocyte cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during bundle of His cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
AV node cell to bundle of His cell communicationSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of heart rate by cardiac conductionSodium channel protein type 5 subunit alphaHomo sapiens (human)
membrane depolarization during atrial cardiac muscle cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
regulation of sodium ion transmembrane transportSodium channel protein type 5 subunit alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
voltage-gated sodium channel activitySodium channel protein type 5 subunit alphaHomo sapiens (human)
protein bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
calmodulin bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
fibroblast growth factor bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
enzyme bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
protein kinase bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
protein domain specific bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
ankyrin bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
ubiquitin protein ligase bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
transmembrane transporter bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
nitric-oxide synthase bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
voltage-gated sodium channel activity involved in cardiac muscle cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
voltage-gated sodium channel activity involved in AV node cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
voltage-gated sodium channel activity involved in bundle of His cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
voltage-gated sodium channel activity involved in Purkinje myocyte action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
voltage-gated sodium channel activity involved in SA node cell action potentialSodium channel protein type 5 subunit alphaHomo sapiens (human)
scaffold protein bindingSodium channel protein type 5 subunit alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
caveolaSodium channel protein type 5 subunit alphaHomo sapiens (human)
nucleoplasmSodium channel protein type 5 subunit alphaHomo sapiens (human)
nucleolusSodium channel protein type 5 subunit alphaHomo sapiens (human)
endoplasmic reticulumSodium channel protein type 5 subunit alphaHomo sapiens (human)
plasma membraneSodium channel protein type 5 subunit alphaHomo sapiens (human)
caveolaSodium channel protein type 5 subunit alphaHomo sapiens (human)
cell surfaceSodium channel protein type 5 subunit alphaHomo sapiens (human)
intercalated discSodium channel protein type 5 subunit alphaHomo sapiens (human)
membraneSodium channel protein type 5 subunit alphaHomo sapiens (human)
lateral plasma membraneSodium channel protein type 5 subunit alphaHomo sapiens (human)
Z discSodium channel protein type 5 subunit alphaHomo sapiens (human)
T-tubuleSodium channel protein type 5 subunit alphaHomo sapiens (human)
sarcolemmaSodium channel protein type 5 subunit alphaHomo sapiens (human)
perinuclear region of cytoplasmSodium channel protein type 5 subunit alphaHomo sapiens (human)
voltage-gated sodium channel complexSodium channel protein type 5 subunit alphaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID655930Antiarrhythmic activity in guinea pig left atria assessed as increase of 1 Hz-induced alternating current arrhythmia at 10'-4 M after 60 mins relative to control2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655946Apparent permeability from basolateral to apical side in human Caco2 cells after 21 days by UV spectroscopy2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655942Vasorelaxant activity in potassium depolarized guinea pig aortic strip assessed as inhibition of calcium-induced contraction at 10'-4 M2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655945Apparent permeability from apical to basolateral side in human Caco2 cells after 21 days by UV spectroscopy2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655926Blockade of human full-length NaV1.5 expressed in HEK293 cells co-transfected with pCD8-IRES-hbeta1 assessed as 10 Hz of use-dependent-induced channel current at -120 mV holding potential after 36 to 72 hrs by patch clamp assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655927Ratio of mexiletine IC50 to compound IC50 for human full-length NaV1.2 at half maximal tonic block2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655928Ratio of mexiletine IC50 to compound IC50 for human full-length NaV1.2 at phasic block2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655943Neurotoxicity in mouse assessed as deffect in motor coordination at 25 to 50 mg/kg, po after 15 to 45 mins by rotarod test2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655947Efflux ratio of permeability from basolateral to apical side to apical to basolateral side in human Caco2 cells after 21 days by UV spectroscopy2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655937Negative chronotropic activity in guinea pig spontaneously beating right atria assessed as decrease in atrial rate at 10'-4 M relative to control2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655944Cytotoxicity against human HepG2 cells assessed as cell viability after 2 hrs by MTT assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID759289Relaxtant activity in guinea pig K+-depolarized ileum longitudinal smooth muscle assessed as inhibition of calcium-induced contraction2013European journal of medicinal chemistry, Jul, Volume: 65Searching for new antiarrhythmic agents: evaluation of meta-hydroxymexiletine enantiomers.
AID655935Negative inotropic activity in guinea pig left atria assessed as decrease of 1 Hz current-induced developed tension at 5 x 10'-5 M relative to control2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655940Negative inotropic activity in guinea pig left atria assessed as decrease of 1 Hz current-induced developed tension2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID759288Relaxtant activity in guinea pig K+-depolarized ileum longitudinal smooth muscle assessed as inhibition of calcium-induced contraction at 10'-4 M relative to control2013European journal of medicinal chemistry, Jul, Volume: 65Searching for new antiarrhythmic agents: evaluation of meta-hydroxymexiletine enantiomers.
AID655931Antiarrhythmic activity in guinea pig left atria assessed as increase of 1 Hz-induced alternating current arrhythmia after 60 mins2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
AID655925Blockade of human full-length NaV1.5 expressed in HEK293 cells co-transfected with pCD8-IRES-hbeta1 assessed as 0.1 Hz of half-maximal tonic-induced channel current at -120 mV holding potential after 36 to 72 hrs by patch clamp assay2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Synthesis and toxicopharmacological evaluation of m-hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (100.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
amiodarone
Amiodarone: An antianginal and class III antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting POTASSIUM CHANNELS and VOLTAGE-GATED SODIUM CHANNELS. There is a resulting decrease in heart rate and in vascular resistance.. amiodarone : A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.		2.07101-benzofurans;
aromatic ketone;
organoiodine compound;
tertiary amino compound		cardiovascular drug
lidocaine
Lidocaine: A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.. lidocaine : The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.		2.0710benzenes;
monocarboxylic acid amide;
tertiary amino compound		anti-arrhythmia drug;
drug allergen;
environmental contaminant;
local anaesthetic;
xenobiotic
mexiletine
Mexiletine: Antiarrhythmic agent pharmacologically similar to LIDOCAINE. It may have some anticonvulsant properties.. mexiletine : An aromatic ether which is 2,6-dimethylphenyl ether of 2-aminopropan-1-ol.		2.9940aromatic ether;
primary amino compound		anti-arrhythmia drug
procainamide
Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.		2.0710benzamidesanti-arrhythmia drug;
platelet aggregation inhibitor;
sodium channel blocker
procaine
Procaine: A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016).. procaine : A benzoate ester, formally the result of esterification of 4-aminobenzoic acid with 2-diethylaminoethanol but formed experimentally by reaction of ethyl 4-aminobenzoate with 2-diethylaminoethanol.		2.0710benzoate ester;
substituted aniline;
tertiary amino compound		central nervous system depressant;
drug allergen;
local anaesthetic;
peripheral nervous system drug
quinidine
Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.		2.0710cinchona alkaloidalpha-adrenergic antagonist;
anti-arrhythmia drug;
antimalarial;
drug allergen;
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor;
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor;
muscarinic antagonist;
P450 inhibitor;
potassium channel blocker;
sodium channel blocker
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		2.0710cyclodextrin
ConditionIndicatedRelationship StrengthStudiesTrials
Ataxia
Impairment of the ability to perform smoothly coordinated voluntary movements. This condition may affect the limbs, trunk, eyes, pharynx, larynx, and other structures. Ataxia may result from impaired sensory or motor function. Sensory ataxia may result from posterior column injury or PERIPHERAL NERVE DISEASES. Motor ataxia may be associated with CEREBELLAR DISEASES; CEREBRAL CORTEX diseases; THALAMIC DISEASES; BASAL GANGLIA DISEASES; injury to the RED NUCLEUS; and other conditions.		02.0710
Auricular Fibrillation
[description not available]		02.0810
Atrial Fibrillation
Abnormal cardiac rhythm that is characterized by rapid, uncoordinated firing of electrical impulses in the upper chambers of the heart (HEART ATRIA). In such case, blood cannot be effectively pumped into the lower chambers of the heart (HEART VENTRICLES). It is caused by abnormal impulse generation.		02.0810