Page last updated: 2024-12-07

5-hydroxypropafenone

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

5-Hydroxypropafenone is a hydroxylated derivative of propafenone, a class IC antiarrhythmic agent. It has been shown to exhibit antiarrhythmic activity in animal models and has been investigated for its potential therapeutic use in humans. However, it has not been approved for clinical use and research on 5-hydroxypropafenone remains limited. The compound's synthesis involves the introduction of a hydroxyl group at the 5-position of propafenone. Further research is needed to fully elucidate its pharmacological properties, potential therapeutic applications, and safety profile.'

Cross-References

ID SourceID
PubMed CID107927
CHEMBL ID1264
CHEBI ID171897
SCHEMBL ID2739132
MeSH IDM0129537

Synonyms (20)

Synonym
86384-10-3
CHEBI:171897
1-[5-hydroxy-2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one
5-hydroxypropafenone
1-propanone, 1-(5-hydroxy-2-(2-hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-
1-(5-hydroxy-2-(2-hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-1-propanone
bdbm50134995
1-(5-hydroxy-2-(2-hydroxy-3-(propylamino)propoxy)phenyl)-3-phenylpropan-1-one
1-[5-hydroxy-2-(2-hydroxy-3-propylamino-propoxy)-phenyl]-3-phenyl-propan-1-one
5-hydroxy propafenone
CHEMBL1264 ,
AKOS000277050
7ac8bf38np ,
unii-7ac8bf38np
SCHEMBL2739132
gpv-129
Q27266815
DTXSID701006775
1-{5-hydroxy-2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one
lu 40-545 d5

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The renal clearance and half-life of digoxin were not significantly altered by propafenone."( Effects of coadministration of propafenone on the pharmacokinetics of digoxin in healthy volunteer subjects.
Erstad, BL; Furman, C; Hoyer, GL; Kirsten, EB; Marcus, FI; Nolan, PE, 1989
)
0.28
" After 1 month of treatment the plasma elimination half-life of propafenone (6."( Pharmacokinetics and pharmacodynamics of propafenone during acute and chronic administration.
Bianchini, C; Ferrario, G; Giani, P; Giudici, V; Landolina, M; Latini, R; Marchi, S; Riva, E, 1988
)
0.27
" EMs were characterized by a shorter propafenone elimination half-life (5."( Polymorphism of propafenone metabolism and disposition in man: clinical and pharmacokinetic consequences.
McAllister, CB; Roden, DM; Siddoway, LA; Thompson, KA; Wang, T; Wilkinson, GR; Woosley, RL, 1987
)
0.27
" The method was successfully applied to a pharmacokinetic study of PPF and 5-OHP in healthy Chinese volunteers."( A Sensitive and Rapid LC-MS-MS Method for Simultaneous Determination of Propafenone and Its Active Metabolite 5-Hydroxypropafenone in Human Plasma and Its Application in a Pharmacokinetic Study.
Chi, Z; Ding, L; Li, Y; Liu, R; Shu, C; Wang, K, 2017
)
0.67

Bioavailability

ExcerptReferenceRelevance
" The total body clearance of propafenone was 963 ml/min, the terminal half-life 198 min and its absolute bioavailability was 15."( Nonlinear kinetics of propafenone metabolites in healthy man.
Follath, F; Ha, HR; Haefeli, W; Vlcek, J; Vozeh, S, 1990
)
0.28

Dosage Studied

ExcerptRelevanceReference
" dosing in selected patients."( Pharmacokinetics and pharmacodynamics of propafenone during acute and chronic administration.
Bianchini, C; Ferrario, G; Giani, P; Giudici, V; Landolina, M; Latini, R; Marchi, S; Riva, E, 1988
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Potassium voltage-gated channel subfamily H member 2Homo sapiens (human)IC50 (µMol)40.00000.00091.901410.0000AID240820
[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)
ATP-dependent translocase ABCB1Homo sapiens (human)EC50 (µMol)3.02100.01600.67863.1000AID281137
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
G2/M transition of mitotic cell cycleATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic metabolic processATP-dependent translocase ABCB1Homo sapiens (human)
response to xenobiotic stimulusATP-dependent translocase ABCB1Homo sapiens (human)
phospholipid translocationATP-dependent translocase ABCB1Homo sapiens (human)
terpenoid transportATP-dependent translocase ABCB1Homo sapiens (human)
regulation of response to osmotic stressATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
transepithelial transportATP-dependent translocase ABCB1Homo sapiens (human)
stem cell proliferationATP-dependent translocase ABCB1Homo sapiens (human)
ceramide translocationATP-dependent translocase ABCB1Homo sapiens (human)
export across plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
positive regulation of anion channel activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transportATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic detoxification by transmembrane export across the plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transport across blood-brain barrierATP-dependent translocase ABCB1Homo sapiens (human)
regulation of chloride transportATP-dependent translocase ABCB1Homo sapiens (human)
regulation of heart rate by cardiac conductionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of heart rate by hormonePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of membrane potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
positive regulation of DNA-templated transcriptionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion homeostasisPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cardiac muscle contractionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of ventricular cardiac muscle cell membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cellular response to xenobiotic stimulusPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
ventricular cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane depolarization during action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of heart rate by cardiac conductionPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion export across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
membrane repolarization during ventricular cardiac muscle cell action potentialPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
negative regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
positive regulation of potassium ion transmembrane transportPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
negative regulation of potassium ion export across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
potassium ion import across plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (24)

Processvia Protein(s)Taxonomy
protein bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATP bindingATP-dependent translocase ABCB1Homo sapiens (human)
ABC-type xenobiotic transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
efflux transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ATP hydrolysis activityATP-dependent translocase ABCB1Homo sapiens (human)
transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
ubiquitin protein ligase bindingATP-dependent translocase ABCB1Homo sapiens (human)
ATPase-coupled transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
xenobiotic transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
carboxylic acid transmembrane transporter activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylcholine floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
phosphatidylethanolamine flippase activityATP-dependent translocase ABCB1Homo sapiens (human)
ceramide floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
floppase activityATP-dependent translocase ABCB1Homo sapiens (human)
transcription cis-regulatory region bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
inward rectifier potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
delayed rectifier potassium channel activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
ubiquitin protein ligase bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
identical protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
protein homodimerization activityPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
C3HC4-type RING finger domain bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activity involved in cardiac muscle cell action potential repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
scaffold protein bindingPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarizationPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

Processvia Protein(s)Taxonomy
cytoplasmATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
cell surfaceATP-dependent translocase ABCB1Homo sapiens (human)
membraneATP-dependent translocase ABCB1Homo sapiens (human)
apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
extracellular exosomeATP-dependent translocase ABCB1Homo sapiens (human)
external side of apical plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membraneATP-dependent translocase ABCB1Homo sapiens (human)
plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
cell surfacePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
perinuclear region of cytoplasmPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
voltage-gated potassium channel complexPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
inward rectifier potassium channel complexPotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
plasma membranePotassium voltage-gated channel subfamily H member 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID44361In vitro multi drug resistance (MDR) reversal inhibitory activity against CCRF-CEM/VCR-1000 cell line2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.
AID29120Calculated partition coefficient (clogP) (Molgen)2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.
AID240820Inhibitory concentration against IKr potassium channel2004Bioorganic & medicinal chemistry letters, Sep-20, Volume: 14, Issue:18
The pharmacophore hypotheses of I(Kr) potassium channel blockers: novel class III antiarrhythmic agents.
AID29119Calculated partition coefficient (clogP) (HINT)2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.
AID281137Inhibition of P-glycoprotein expressed in MDR CCRF vcr1000 cells by daunorubicin efflux assay2007Journal of medicinal chemistry, Apr-05, Volume: 50, Issue:7
Self-organizing maps for identification of new inhibitors of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

TimeframeStudies, This Drug (%)All Drugs %
pre-199020 (35.09)18.7374
1990's23 (40.35)18.2507
2000's10 (17.54)29.6817
2010's4 (7.02)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: 10.09

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 Index10.09 (24.57)
Research Supply Index4.14 (2.92)
Research Growth Index4.23 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (5.08%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (5.08%)4.05%
Observational0 (0.00%)0.25%
Other53 (89.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]