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diprafenone

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

Description

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

Cross-References

ID SourceID
PubMed CID71249
CHEMBL ID441809
CHEBI ID135559
SCHEMBL ID563653
MeSH IDM0137268

Synonyms (23)

Synonym
85414-47-7
CHEMBL441809
1-propanone, 1-(2-(3-((1,1-dimethylpropyl)amino)-2-hydroxypropoxy)phenyl)-3-phenyl-
sa-76
diprafenone
diprafenona [spanish]
diprafenonum [latin]
diprafenone [inn]
(+-)-2'-(2-hydroxy-3-(tert-pentylamino)propoxy)-3-phenylpropiophenone
CHEBI:135559
1-[2-[2-hydroxy-3-(2-methylbutan-2-ylamino)propoxy]phenyl]-3-phenylpropan-1-one
81447-80-5
diprafenonum
unii-1p35md5c1f
1p35md5c1f ,
diprafenona
1-[2-[2-hydroxy-3-(2-methylbutan-2-ylamino)propoxy]phenyl]-3-phenyl-propan-1-one
SCHEMBL563653
diprafenone [who-dd]
(+/-)-2'-(2-hydroxy-3-(tert-pentylamino)propoxy)-3-phenylpropiophenone
DTXSID10868613
(+/-)-diprafenone
Q15634017

Research Excerpts

Overview

Diprafenone is a new antiarrhythmic drug with a dominant local anaesthetic action and an additional beta-sympathicolytic activity. It is structurally similar to propafenone.

ExcerptReferenceRelevance
"Diprafenone is a new antiarrhythmic agent with a dominant local anesthetic action and additional beta-sympathicolytic activity. "( [Diprafenone--comparative study of anti-arrhythmia therapy with propafenone].
Geibel, A; Hohnloser, S; Just, H; Landsrath, C; Meinertz, T; Zehender, M, 1988
)
2.63
"Diprafenone is a new antiarrhythmic agent currently under clinical investigation, with close chemical similarity to propafenone. "( [Electrophysiologic and hemodynamic effects of the new anti-arrhythmia agent diprafenone].
Behrenbeck, T; Gülker, H; Heuer, H; Thale, J, 1987
)
1.94
"Diprafenone is a new antiarrhythmic drug with a dominant local anaesthetic action and an additional beta-sympathicolytic activity. "( [Treatment of chronic ventricular arrhythmias with the new class Ic anti-arrhythmia agent diprafenon--results of long-term therapy].
Behrenbeck, T; Frenking, B; Gülker, H; Hasfeld, M; Heuer, H, 1987
)
1.72
"Diprafenone (D) is a new class I c antiarrhythmic agent, structurally similar to propafenone. "( Use of diprafenone, a new potent propafenone-analogue, in acute experimental myocardial ischaemia and infarction.
Bender, F; Gülker, H; Haverkamp, W; Hindricks, G; Thale, J, 1987
)
2.17

Effects

ExcerptReferenceRelevance
"Diprafenone has significant beta-adrenoceptor blocking activity which may contribute to its efficacy as an antiarrhythmic agent and allow its use in treatment of arrhythmias refractory to therapy with class I and class II agents alone."( Beta-adrenoceptor blocking activity of diprafenone in anesthetized dogs: comparison with propafenone and propranolol.
Cantor, E; Greenberg, S; Paul, J, 1989
)
1.27

Pharmacokinetics

The most important pharmacokinetic parameters (Cmax, t1/2, AUC) and the relative oral availability of a solid oral preparation of racemic diprafenone were investigated. In an open, randomised, crossover trial, the terminal half-life of elimination was 1.

ExcerptReferenceRelevance
" Blood and urine samples were collected for pharmacokinetic analyses."( Effect of diprafenone on the pharmacokinetics of digoxin.
Alken, RG; Koytchev, R; Mayer, O, 1996
)
0.7
"The most important pharmacokinetic parameters (Cmax, t1/2, AUC) and the relative oral availability of a solid oral preparation of racemic diprafenone were investigated when administered to fasting subjects and 10 min after a standard meal, in an open, randomised, crossover trial."( Influence of food on the bioavailability and some pharmacokinetic parameters of diprafenone--a novel antiarrhythmic agent.
Alken, RG; Greenwood, M; Koytchev, R; Mayer, O; Smith, I, 1996
)
0.72
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

Food increased the oral bioavailability of diprafenone by approximately 50%.

ExcerptReferenceRelevance
" Following oral administration, a dose-dependent increase in bioavailability from 10."( Pharmacokinetic characterization of the antiarrhythmic drug diprafenone in man.
Jähnchen, E; Sachs, W; Trenk, D; Wagner, F, 1989
)
0.52
"The present study was done to investigate the effect of food on the bioavailability of diprafenone."( Influence of food on the bioavailability and some pharmacokinetic parameters of diprafenone--a novel antiarrhythmic agent.
Alken, RG; Greenwood, M; Koytchev, R; Mayer, O; Smith, I, 1996
)
0.74
"Food increased the oral bioavailability of diprafenone by approximately 50%."( Influence of food on the bioavailability and some pharmacokinetic parameters of diprafenone--a novel antiarrhythmic agent.
Alken, RG; Greenwood, M; Koytchev, R; Mayer, O; Smith, I, 1996
)
0.78
"The quantitative structure-bioavailability relationship of 232 structurally diverse drugs was studied to evaluate the feasibility of constructing a predictive model for the human oral bioavailability of prospective new medicinal agents."( QSAR model for drug human oral bioavailability.
Topliss, JG; Yoshida, F, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
" dosing highest levels of radioactivity were found in the lung; after oral application in the gastrointestinal tract."( Pharmacokinetics and metabolism of the antiarrhythmic agent [3H]-diprafenone in the rat.
Brunner, F; Kolmayr, U; Kukovetz, WR, 1989
)
0.51
" Within 20-30 min, both optical enantiomers caused a Vmax depression which occurred predominantly as a phasic blockade at a low dosage (10 mumol/l)."( Inhibitory effects of diprafenone stereoenantiomers on cardiac Na+ channels.
Fichtner, H; Kohlhardt, M, 1988
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aromatic compoundA cyclically conjugated molecular entity with a stability (due to delocalization) significantly greater than that of a hypothetical localized structure (e.g. Kekule structure) is said to possess aromatic character.
[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]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID29359Ionization constant (pKa)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID27167Delta logD (logD6.5 - logD7.4)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID28681Partition coefficient (logD6.5)2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID29812Oral bioavailability in human2000Journal of medicinal chemistry, Jun-29, Volume: 43, Issue:13
QSAR model for drug human oral bioavailability.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (45.45)18.7374
1990's15 (45.45)18.2507
2000's3 (9.09)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (14.71%)5.53%
Reviews1 (2.94%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other28 (82.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]