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Identification
NamePropafenone
Accession NumberDB01182  (APRD00261)
TypeSmall Molecule
GroupsApproved
Description

An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity. The drug is generally well tolerated. [PubChem]

Structure
Thumb
Synonyms
1-(2-(2-Hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-1-propanone
2-(2'-Hydroxy-3'-propylaminopropoxy)-omega-phenylpropiophenone
Propafenona
Propafenonum
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mylan-propafenonetablet300 mgoralMylan Pharmaceuticals Ulc2002-03-08Not applicableCanada
Mylan-propafenonetablet150 mgoralMylan Pharmaceuticals Ulc2002-03-08Not applicableCanada
Nu-propafenonetablet150 mgoralNu Pharm IncNot applicableNot applicableCanada
PMS-propafenonetablet150 mgoralPharmascience Inc2001-04-09Not applicableCanada
PMS-propafenonetablet300 mgoralPharmascience Inc2008-02-22Not applicableCanada
PMS-propafenonetablet150 mgoralPharmascience Inc2008-02-22Not applicableCanada
PMS-propafenonetablet300 mgoralPharmascience Inc2001-04-09Not applicableCanada
Propafenonetablet150 mgoralSanis Health Inc2010-02-16Not applicableCanada
Propafenonetablet300 mgoralSanis Health Inc2010-02-16Not applicableCanada
Propafenone Hydrochloride SRcapsule, extended release425 mg/1oralPrasco Laboratories2014-10-222016-04-05Us
Propafenone Hydrochloride SRcapsule, extended release325 mg/1oralPrasco Laboratories2014-10-222016-04-05Us
Propafenone Hydrochloride SRcapsule, extended release225 mg/1oralPrasco Laboratories2014-10-222016-04-05Us
Propafenone-150tablet150 mgoralPro Doc Limitee2008-03-07Not applicableCanada
Propafenone-300tablet300 mgoralPro Doc Limitee2009-05-26Not applicableCanada
Rythmoltablet, film coated150 mg/1oralGlaxo Smith Kline Llc2010-01-042016-04-23Us
Rythmoltablet300 mgoralBgp Pharma Ulc1988-12-31Not applicableCanada
Rythmoltablet150 mgoralBgp Pharma Ulc1988-12-31Not applicableCanada
Rythmoltablet, film coated225 mg/1oralGlaxo Smith Kline Llc2010-01-042016-04-23Us
Rythmol SRcapsule, extended release425 mg/1oralGlaxo Smith Kline Llc2011-03-172016-04-23Us
Rythmol SRcapsule, extended release325 mg/1oralGlaxo Smith Kline Llc2011-03-172016-04-23Us
Rythmol SRcapsule, extended release225 mg/1oralGlaxo Smith Kline Llc2011-03-172016-04-23Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-propafenonetablet300 mgoralApotex Inc2001-02-22Not applicableCanada
Apo-propafenonetablet150 mgoralApotex Inc2001-02-22Not applicableCanada
Propafenonecapsule, extended release325 mg/1oralRebel Distributors Corp2011-01-032016-04-05Us
Propafenone HCltablet, film coated150 mg/1oralActavis Pharma, Inc.2000-10-242016-04-23Us
Propafenone HCltablet, film coated225 mg/1oralAvera Mc Kennan Hospital2015-10-012016-04-05Us
Propafenone HCltablet, film coated150 mg/1oralAmerican Health Packaging2012-05-012016-04-05Us
Propafenone HCltablet, film coated225 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2012-09-102016-04-05Us
Propafenone HCltablet, film coated150 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2012-09-102016-04-05Us
Propafenone HCltablet, film coated225 mg/1oralActavis Pharma, Inc.2000-10-242016-04-23Us
Propafenone Hydrochloridecapsule, extended release425 mg/1oralGolden State Medical Supply, Inc.2015-09-152016-04-05Us
Propafenone Hydrochloridetablet, film coated225 mg/1oralMutual Pharmaceutical Co., Inc.2001-11-292016-04-05Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2002-10-172016-04-23Us
Propafenone Hydrochloridecapsule, extended release325 mg/1oralGolden State Medical Supply, Inc.2015-09-152016-04-05Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralbryant ranch prepack2002-10-172016-04-05Us
Propafenone Hydrochloridetablet, film coated300 mg/1oralMutual Pharmaceutical Co., Inc.2001-11-292016-04-05Us
Propafenone Hydrochloridetablet, film coated300 mg/1oralQualitest Pharmaceuticals2002-10-172016-04-23Us
Propafenone Hydrochloridecapsule, extended release225 mg/1oralGolden State Medical Supply, Inc.2015-09-152016-04-05Us
Propafenone Hydrochloridetablet, coated300 mg/1oralANI Pharmaceuticals, Inc.2015-03-312016-04-05Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralMutual Pharmaceutical Co., Inc.2001-11-292016-04-05Us
Propafenone Hydrochloridetablet, coated225 mg/1oralANI Pharmaceuticals, Inc.2015-03-312016-04-05Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralMylan Institutional Inc.2003-02-012016-04-05Us
Propafenone Hydrochloridetablet, film coated225 mg/1oralQualitest Pharmaceuticals2002-10-172016-04-23Us
Propafenone Hydrochloridecapsule, extended release325 mg/1oralAmerican Health Packaging2015-03-312016-04-05Us
Propafenone Hydrochloridetablet, coated150 mg/1oralANI Pharmaceuticals, Inc.2015-03-312016-04-05Us
Propafenone Hydrochloridecapsule, extended release425 mg/1oralAv Kare, Inc.2016-01-212016-04-05Us
Propafenone Hydrochloridecapsule, extended release425 mg/1oralPar Pharmaceutical, Inc.2011-01-032016-04-05Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralQualitest Pharmaceuticals2002-10-172016-04-23Us
Propafenone Hydrochloridecapsule, extended release225 mg/1oralAmerican Health Packaging2014-10-202016-12-31Us
Propafenone Hydrochloridecapsule, extended release225 1/1oralAmerican Health Packaging2015-10-012016-04-05Us
Propafenone Hydrochloridecapsule, extended release325 mg/1oralAv Kare, Inc.2016-01-212016-04-05Us
Propafenone Hydrochloridecapsule, extended release325 mg/1oralPar Pharmaceutical, Inc.2011-01-032016-04-05Us
Propafenone Hydrochloridecapsule, extended release425 mg/1oralActavis Pharma, Inc.2015-10-152016-04-23Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralCardinal Health2011-05-202016-04-05Us
Propafenone Hydrochloridecapsule, extended release225 mg/1oralAv Kare, Inc.2016-01-212016-04-05Us
Propafenone Hydrochloridecapsule, extended release225 1/1oralPar Pharmaceutical, Inc.2011-01-032016-04-05Us
Propafenone Hydrochloridecapsule, extended release325 mg/1oralActavis Pharma, Inc.2015-10-152016-04-23Us
Propafenone Hydrochloridetablet, film coated225 mg/1oralPhysicians Total Care, Inc.2008-10-092016-04-05Us
Propafenone Hydrochloridecapsule, extended release225 mg/1oralPar Pharmaceutical, Inc.2011-01-032016-04-05Us
Propafenone Hydrochloridecapsule, extended release225 mg/1oralActavis Pharma, Inc.2015-10-152016-04-23Us
Propafenone Hydrochloridetablet, film coated150 mg/1oralPhysicians Total Care, Inc.2005-05-182016-04-05Us
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Propafenone hydrochloride
34183-22-7
Thumb
  • InChI Key: XWIHRGFIPXWGEF-UHFFFAOYNA-N
  • Monoisotopic Mass: 377.175771474
  • Average Mass: 377.905
DBSALT000148
Categories
UNII68IQX3T69U
CAS number54063-53-5
WeightAverage: 341.444
Monoisotopic: 341.199093735
Chemical FormulaC21H27NO3
InChI KeyInChIKey=JWHAUXFOSRPERK-UHFFFAOYSA-N
InChI
InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3
IUPAC Name
1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one
SMILES
CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chalcones and dihydrochalcones. These are organic compounds containing 1,3-Diphenylpropenone (benzylideneacetophenone), ArCH=CH(=O)Ar,or its derivatives formed by substitution.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct ParentChalcones and dihydrochalcones
Alternative Parents
Substituents
  • Chalcone or dihydrochalcone
  • Butyrophenone
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Ketone
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed to prolong the time to recurrence of paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms in patients without structural heart disease. Also used for the treatment of life-threatening documented ventricular arrhythmias, such as sustained ventricular tachycardia.
PharmacodynamicsPropafenone is a Class 1C antiarrhythmic drug with local anesthetic effects, and a direct stabilizing action on myocardial membranes. It is used in the treatment of atrial and ventricular arrhythmias. It works by slowing the influx of sodium ions into the cardiac muscle cells, causing a decrease in excitablity of the cells. Propafenone has local anesthetic activity approximately equal to procaine.
Mechanism of actionThe electrophysiological effect of propafenone manifests itself in a reduction of upstroke velocity (Phase 0) of the monophasic action potential. In Purkinje fibers, and to a lesser extent myocardial fibers, propafenone reduces the fast inward current carried by sodium ions, which is responsible for the drugs antiarrhythmic actions. Diastolic excitability threshold is increased and effective refractory period prolonged. Propafenone reduces spontaneous automaticity and depresses triggered activity. At very high concentrations in vitro, propafenone can inhibit the slow inward current carried by calcium but this calcium antagonist effect probably does not contribute to antiarrhythmic efficacy.
Related Articles
AbsorptionNearly completely absorbed following oral administration (90%). Systemic bioavailability ranges from 5 to 50%, due to significant first-pass metabolism. This wide range in systemic bioavailability is related to two factors: presence of food (food increases bioavailability) and dosage (bioavailability is 3.4% for a 150-mg tablet compared to 10.6% for a 300-mg tablet).
Volume of distribution
  • 252 L
Protein binding97%
Metabolism

Metabolized primarily in the liver where it is rapidly and extensively metabolized to two active metabolites, 5-hydroxypropafenone and N-depropylpropafenone. These metabolites have antiarrhythmic activity comparable to propafenone but are present in concentrations less than 25% of propafenone concentrations.

SubstrateEnzymesProduct
Propafenone
N-desalkylpropafenoneDetails
Propafenone
5-hydroxypropafenoneDetails
Propafenone
Not Available
N-depropylpropafenoneDetails
Route of eliminationApproximately 50% of propafenone metabolites are excreted in the urine following administration of immediate release tablets.
Half life2-10 hours
ClearanceNot Available
ToxicitySymptoms of propafenone overdose (usually most severe within the first 3 hours) may include convulsions (rarely), heartbeat irregularities, low blood pressure, and sleepiness.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.996
Blood Brain Barrier-0.958
Caco-2 permeable-0.5433
P-glycoprotein substrateSubstrate0.8548
P-glycoprotein inhibitor IInhibitor0.8565
P-glycoprotein inhibitor IIInhibitor0.874
Renal organic cation transporterNon-inhibitor0.7204
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.5499
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.7066
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8931
Ames testNon AMES toxic0.8446
CarcinogenicityNon-carcinogens0.8879
BiodegradationNot ready biodegradable0.803
Rat acute toxicity2.3795 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5383
hERG inhibition (predictor II)Inhibitor0.8915
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral150 mg
Tabletoral300 mg
Capsule, extended releaseoral225 1/1
Tablet, coatedoral150 mg/1
Tablet, coatedoral225 mg/1
Tablet, coatedoral300 mg/1
Tablet, film coatedoral300 mg/1
Tablet, film coatedoral150 mg/1
Tablet, film coatedoral225 mg/1
Capsule, extended releaseoral225 mg/1
Capsule, extended releaseoral325 mg/1
Capsule, extended releaseoral425 mg/1
Prices
Unit descriptionCostUnit
Rythmol SR 325 mg 12 Hour Capsule8.9USD capsule
Rythmol SR 425 mg 12 Hour Capsule8.9USD capsule
Rythmol sr 325 mg capsule8.56USD capsule
Rythmol sr 425 mg capsule8.56USD capsule
Rythmol SR 225 mg 12 Hour Capsule7.02USD capsule
Rythmol sr 225 mg capsule6.75USD capsule
Rythmol 225 mg tablet6.2USD tablet
Rythmol 300 mg tablet5.05USD tablet
Rythmol 150 mg tablet3.95USD tablet
Propafenone hcl 300 mg tablet3.03USD tablet
Propafenone hcl 225 mg tablet2.38USD tablet
Rythmol 300 mg Tablet2.09USD tablet
Propafenone hcl 150 mg tablet1.64USD tablet
Rythmol 150 mg Tablet1.18USD tablet
Apo-Propafenone 300 mg Tablet0.79USD tablet
Pms-Propafenone 300 mg Tablet0.79USD tablet
Apo-Propafenone 150 mg Tablet0.45USD tablet
Pms-Propafenone 150 mg Tablet0.45USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5681588 No1994-10-282014-10-28Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySlightly solubleNot Available
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00758 mg/mLALOGPS
logP3.1ALOGPS
logP3.54ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity100.21 m3·mol-1ChemAxon
Polarizability39.75 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Helmut Lietz, “Preparation of propafenone.” U.S. Patent US4474986, issued May, 1974.

US4474986
General ReferencesNot Available
External Links
ATC CodesC01BC03
AHFS Codes
  • 24:04.04.12
PDB EntriesNot Available
FDA labelDownload (91.1 KB)
MSDSDownload (73.7 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Abiraterone can be increased when it is combined with Propafenone.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Propafenone.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Propafenone.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Propafenone.
AmiodaroneThe risk or severity of adverse effects can be increased when Amiodarone is combined with Propafenone.
AprepitantThe serum concentration of Propafenone can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Propafenone.
AtazanavirThe serum concentration of Propafenone can be increased when it is combined with Atazanavir.
BetaxololThe serum concentration of Betaxolol can be increased when it is combined with Propafenone.
BisoprololThe serum concentration of Bisoprolol can be increased when it is combined with Propafenone.
BoceprevirThe serum concentration of Propafenone can be increased when it is combined with Boceprevir.
BretyliumBretylium may increase the bradycardic activities of Propafenone.
BupropionThe serum concentration of Propafenone can be increased when it is combined with Bupropion.
CarbamazepineThe serum concentration of Propafenone can be decreased when it is combined with Carbamazepine.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Propafenone.
CelecoxibThe serum concentration of Celecoxib can be increased when it is combined with Propafenone.
CeritinibPropafenone may increase the bradycardic activities of Ceritinib.
CimetidineThe serum concentration of Propafenone can be increased when it is combined with Cimetidine.
CinacalcetThe serum concentration of Propafenone can be increased when it is combined with Cinacalcet.
CitalopramPropafenone may increase the QTc-prolonging activities of Citalopram.
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Propafenone.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Propafenone.
CobicistatThe serum concentration of Propafenone can be increased when it is combined with Cobicistat.
CocaineThe serum concentration of Propafenone can be increased when it is combined with Cocaine.
ConivaptanThe serum concentration of Propafenone can be increased when it is combined with Conivaptan.
DarifenacinThe serum concentration of Darifenacin can be increased when it is combined with Propafenone.
DarunavirThe serum concentration of Propafenone can be increased when it is combined with Darunavir.
DelavirdineThe serum concentration of Propafenone can be increased when it is combined with Delavirdine.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Propafenone.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Propafenone.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Propafenone.
DiltiazemThe serum concentration of Propafenone can be increased when it is combined with Diltiazem.
DiphenhydramineThe serum concentration of Diphenhydramine can be increased when it is combined with Propafenone.
DisopyramidePropafenone may increase the arrhythmogenic activities of Disopyramide.
DofetilidePropafenone may increase the arrhythmogenic activities of Dofetilide.
DronedaronePropafenone may increase the arrhythmogenic activities of Dronedarone.
DuloxetineThe serum concentration of Duloxetine can be increased when it is combined with Propafenone.
EnzalutamideThe serum concentration of Propafenone can be decreased when it is combined with Enzalutamide.
EsmololThe serum concentration of Esmolol can be increased when it is combined with Propafenone.
EtravirineThe serum concentration of Propafenone can be decreased when it is combined with Etravirine.
FluconazoleThe serum concentration of Propafenone can be increased when it is combined with Fluconazole.
FluoxetinePropafenone may increase the QTc-prolonging activities of Fluoxetine.
FluvoxamineThe serum concentration of Propafenone can be increased when it is combined with Fluvoxamine.
FosamprenavirThe serum concentration of Propafenone can be increased when it is combined with Fosamprenavir.
FosphenytoinThe serum concentration of Propafenone can be decreased when it is combined with Fosphenytoin.
GoserelinGoserelin may increase the QTc-prolonging activities of Propafenone.
IbutilidePropafenone may increase the arrhythmogenic activities of Ibutilide.
IdelalisibThe serum concentration of Propafenone can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Propafenone can be increased when it is combined with Imatinib.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Propafenone.
IndinavirThe serum concentration of Propafenone can be increased when it is combined with Indinavir.
IsavuconazoniumThe serum concentration of Propafenone can be increased when it is combined with Isavuconazonium.
IsoniazidThe serum concentration of Isoniazid can be increased when it is combined with Propafenone.
ItraconazoleThe serum concentration of Propafenone can be increased when it is combined with Itraconazole.
IvabradineIvabradine may increase the QTc-prolonging activities of Propafenone.
KetoconazoleThe serum concentration of Propafenone can be increased when it is combined with Ketoconazole.
LabetalolThe serum concentration of Labetalol can be increased when it is combined with Propafenone.
LacosamidePropafenone may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Propafenone.
LorcaserinThe serum concentration of Lorcaserin can be increased when it is combined with Propafenone.
MethotrimeprazineThe serum concentration of Propafenone can be increased when it is combined with Methotrimeprazine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Propafenone.
MifepristoneMifepristone may increase the QTc-prolonging activities of Propafenone.
MirabegronThe serum concentration of Propafenone can be increased when it is combined with Mirabegron.
MitotaneThe serum concentration of Propafenone can be decreased when it is combined with Mitotane.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Propafenone.
NefazodoneThe serum concentration of Propafenone can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Propafenone can be increased when it is combined with Nelfinavir.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Propafenone.
OctreotideOctreotide may increase the bradycardic activities of Propafenone.
OrlistatThe serum concentration of Propafenone can be decreased when it is combined with Orlistat.
ParoxetineThe serum concentration of Propafenone can be increased when it is combined with Paroxetine.
PenbutololThe serum concentration of Penbutolol can be increased when it is combined with Propafenone.
PhenobarbitalThe serum concentration of Propafenone can be decreased when it is combined with Phenobarbital.
PhenytoinThe serum concentration of Propafenone can be decreased when it is combined with Phenytoin.
PindololThe serum concentration of Pindolol can be increased when it is combined with Propafenone.
PosaconazoleThe serum concentration of Propafenone can be increased when it is combined with Posaconazole.
PrimidoneThe serum concentration of Propafenone can be decreased when it is combined with Primidone.
ProcainamidePropafenone may increase the arrhythmogenic activities of Procainamide.
PropranololThe serum concentration of Propranolol can be increased when it is combined with Propafenone.
QuinidineQuinidine may increase the QTc-prolonging activities of Propafenone.
RifabutinThe serum concentration of Propafenone can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Propafenone can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Propafenone can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Propafenone can be increased when it is combined with Ritonavir.
RolapitantThe serum concentration of Rolapitant can be increased when it is combined with Propafenone.
RuxolitinibRuxolitinib may increase the bradycardic activities of Propafenone.
SaquinavirSaquinavir may increase the arrhythmogenic activities of Propafenone.
SertralineSertraline may increase the QTc-prolonging activities of Propafenone.
SotalolPropafenone may increase the arrhythmogenic activities of Sotalol.
St. John's WortThe serum concentration of Propafenone can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Propafenone can be increased when it is combined with Stiripentol.
TelaprevirThe risk or severity of adverse effects can be increased when Telaprevir is combined with Propafenone.
TerbinafineThe serum concentration of Propafenone can be increased when it is combined with Terbinafine.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Propafenone.
TiclopidineThe serum concentration of Ticlopidine can be increased when it is combined with Propafenone.
TimololThe serum concentration of Timolol can be increased when it is combined with Propafenone.
TipranavirThe serum concentration of Propafenone can be increased when it is combined with Tipranavir.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Propafenone.
TofacitinibTofacitinib may increase the bradycardic activities of Propafenone.
TranylcypromineThe serum concentration of Tranylcypromine can be increased when it is combined with Propafenone.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Propafenone.
VerapamilThe serum concentration of Propafenone can be increased when it is combined with Verapamil.
VoriconazoleThe serum concentration of Propafenone can be increased when it is combined with Voriconazole.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Propafenone.
Food Interactions
  • Always take at the same time in regard to meals.
  • Grapefruit and grapefruit juice should be avoided throughout treatment. Grapefruit can increase serum levels of this product.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Mergenthaler J, Haverkamp W, Huttenhofer A, Skryabin BV, Musshoff U, Borggrefe M, Speckmann EJ, Breithardt G, Madeja M: Blocking effects of the antiarrhythmic drug propafenone on the HERG potassium channel. Naunyn Schmiedebergs Arch Pharmacol. 2001 Apr;363(4):472-80. [PubMed:11330342 ]
  2. Arias C, Gonzalez T, Moreno I, Caballero R, Delpon E, Tamargo J, Valenzuela C: Effects of propafenone and its main metabolite, 5-hydroxypropafenone, on HERG channels. Cardiovasc Res. 2003 Mar;57(3):660-9. [PubMed:12618228 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. [PubMed:8423765 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. [PubMed:8423765 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Schmid D, Ecker G, Kopp S, Hitzler M, Chiba P: Structure-activity relationship studies of propafenone analogs based on P-glycoprotein ATPase activity measurements. Biochem Pharmacol. 1999 Nov 1;58(9):1447-56. [PubMed:10513988 ]
  2. Bachmakov I, Rekersbrink S, Hofmann U, Eichelbaum M, Fromm MF: Characterisation of (R/S)-propafenone and its metabolites as substrates and inhibitors of P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2005 Mar;371(3):195-201. Epub 2005 Apr 15. [PubMed:15900513 ]
  3. Singh P, Paul K: Studies of interactions between uracil-based hybrid molecules and P-glycoprotein--search for multidrug resistance modulators. Bioorg Med Chem. 2006 Nov 1;14(21):7183-6. Epub 2006 Jul 14. [PubMed:16843673 ]
  4. Woodland C, Verjee Z, Giesbrecht E, Koren G, Ito S: The digoxin-propafenone interaction: characterization of a mechanism using renal tubular cell monolayers. J Pharmacol Exp Ther. 1997 Oct;283(1):39-45. [PubMed:9336306 ]
  5. Tmej C, Chiba P, Huber M, Richter E, Hitzler M, Schaper KJ, Ecker G: A combined Hansch/Free-Wilson approach as predictive tool in QSAR studies on propafenone-type modulators of multidrug resistance. Arch Pharm (Weinheim). 1998 Jul-Aug;331(7-8):233-40. [PubMed:9747179 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13