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Identification
NameProcainamide
Accession NumberDB01035  (APRD00509)
TypeSmall Molecule
GroupsApproved
DescriptionA derivative of procaine with less CNS action. [PubChem]
Structure
Thumb
Synonyms
Biocoryl
p-Amino-N-(2-diethylaminoethyl)benzamide
p-Aminobenzoic diethylaminoethylamide
Procainamida
Procainamide
Procainamidum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Procainamide Hydrochloride Inj. USPsolution100 mgintramuscular; intravenousSandoz Canada Incorporated1995-12-31Not applicableCanada
Procainamide-250 Cap 250mgcapsule250 mgoralPro Doc Limitee1987-12-312000-07-31Canada
Procainamide-375 Cap 375mgcapsule375 mgoralPro Doc Limitee1987-12-312000-07-31Canada
Procainamide-500 Cap 500mgcapsule500 mgoralPro Doc Limitee1987-12-312000-07-31Canada
Procan SRtablet (extended-release)250 mgoralErfa Canada 2012 Inc1985-12-31Not applicableCanada
Procan SRtablet (extended-release)500 mgoralErfa Canada 2012 Inc1985-12-312015-06-05Canada
Procan SRtablet (extended-release)750 mgoralErfa Canada 2012 Inc1985-12-312015-06-05Canada
Pronestyl Cap 250mgcapsule250 mgoralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1955-12-312002-07-30Canada
Pronestyl Cap 375mgcapsule375 mgoralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1973-12-312002-07-30Canada
Pronestyl Cap 500mgcapsule500 mgoralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1976-12-312002-07-30Canada
Pronestyl Inj 100mg/mlliquid100 mgintramuscular; intravenousSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1955-12-312002-07-30Canada
Pronestyl-SR Tab 500mgtablet (extended-release)500 mgoralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1984-12-312005-08-01Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-procainamide Cap 250mgcapsule250 mgoralApotex Inc1986-12-31Not applicableCanada
Apo-procainamide Cap 375mgcapsule375 goralApotex Inc1986-12-31Not applicableCanada
Apo-procainamide Cap 500mgcapsule500 mgoralApotex Inc1986-12-31Not applicableCanada
Procainamide Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousHospira, Inc.1986-02-12Not applicableUs
Procainamide Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousMc Kesson Packaging Services Business Unit Of Mc Kesson Corporation2010-02-01Not applicableUs
Procainamide Hydrochlorideinjection, solution500 mg/mLintramuscular; intravenousHospira, Inc.1986-02-12Not applicableUs
Procainamide Hydrochlorideinjection, solution500 mg/mLintramuscular; intravenousCardinal Health1986-02-12Not applicableUs
Procainamide Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousCardinal Health2011-07-08Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BiocorylNot Available
ProcanNot Available
ProcanbidNot Available
ProcapanNot Available
PronestylNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Procainamide Hydrochloride
Thumb
  • InChI Key: ABTXGJFUQRCPNH-UHFFFAOYSA-N
  • Monoisotopic Mass: 271.145140048
  • Average Mass: 271.786
DBSALT000724
Categories
UNIIL39WTC366D
CAS number51-06-9
WeightAverage: 235.3253
Monoisotopic: 235.168462309
Chemical FormulaC13H21N3O
InChI KeyInChIKey=REQCZEXYDRLIBE-UHFFFAOYSA-N
InChI
InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)
IUPAC Name
4-amino-N-[2-(diethylamino)ethyl]benzamide
SMILES
CCN(CC)CCNC(=O)C1=CC=C(N)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids and derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids and derivatives
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Aminobenzamide
  • Substituted aniline
  • Benzoyl
  • Aniline
  • Primary aromatic amine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of life-threatening ventricular arrhythmias.
PharmacodynamicsProcainamide is an agent indicated for production of local or regional anesthesia and in the treatment of ventricular tachycardia occurring during cardiac manipulation, such as surgery or catheterization, or which may occur during acute myocardial infarction, digitalis toxicity, or other cardiac diseases. The mode of action of the antiarrhythmic effect of Procainamide appears to be similar to that of procaine and quinidine. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole. The sinoatrial node is, however, unaffected.
Mechanism of actionProcainamide is sodium channel blocker. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses thereby effecting local anesthetic action.
Related Articles
Absorption75 to 95%
Volume of distribution
  • 2 L/kg
Protein binding15 to 20%
Metabolism

Hepatic

SubstrateEnzymesProduct
Procainamide
N-Acetyl-3-hydroxyprocainamideDetails
Route of eliminationTrace amounts may be excreted in the urine as free and conjugated p-aminobenzoic acid, 30 to 60 percent as unchanged PA, and 6 to 52 percent as the NAPA derivative.
Half life~2.5-4.5 hours
ClearanceNot Available
ToxicityLD50=95 mg/kg (rat, IV); LD50=312 mg/kg (mouse, oral); LD50=103 mg/kg (mouse, IV); LD50=250 mg/kg (rabbit, IV)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Procainamide (Antiarrhythmic) Action PathwayDrug actionSMP00324
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9561
Blood Brain Barrier+0.9675
Caco-2 permeable+0.666
P-glycoprotein substrateSubstrate0.7739
P-glycoprotein inhibitor INon-inhibitor0.9452
P-glycoprotein inhibitor IINon-inhibitor0.9654
Renal organic cation transporterNon-inhibitor0.7526
CYP450 2C9 substrateNon-substrate0.8624
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.6306
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9384
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9606
CYP450 3A4 inhibitorNon-inhibitor0.9238
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8833
Ames testNon AMES toxic0.7822
CarcinogenicityNon-carcinogens0.5352
BiodegradationNot ready biodegradable0.9855
Rat acute toxicity2.1133 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9454
hERG inhibition (predictor II)Non-inhibitor0.648
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg
Capsuleoral375 g
Capsuleoral500 mg
Injection, solutionintramuscular; intravenous100 mg/mL
Injection, solutionintramuscular; intravenous500 mg/mL
Solutionintramuscular; intravenous100 mg
Tablet (extended-release)oral250 mg
Tablet (extended-release)oral500 mg
Tablet (extended-release)oral750 mg
Capsuleoral375 mg
Liquidintramuscular; intravenous100 mg
Prices
Unit descriptionCostUnit
Procainamide 500 mg/ml vial6.45USD ml
Procainamide 100 mg/ml vial1.29USD ml
Procan Sr 750 mg Sustained-Release Tablet0.91USD tablet
Procan Sr 500 mg Sustained-Release Tablet0.56USD tablet
Procan Sr 250 mg Sustained-Release Tablet0.4USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5656296 No1994-08-122014-08-12Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point165-169 °CNot Available
water solubility5050 mg/LNot Available
logP0.88HANSCH,C ET AL. (1995)
pKa9.32SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility3.02 mg/mLALOGPS
logP1.42ALOGPS
logP0.95ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)15.75ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.36 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.25 m3·mol-1ChemAxon
Polarizability27.69 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Victor Chu, Zhu Teng, Steve Goss, Ronald Edwards, Kelle Garvey, Timothy Gorzynski, William Bedzyk, “Synthesis and application of procainamide analogs for use in an immunoassay.” U.S. Patent US20050227288, issued October 13, 2005.

US20050227288
General ReferencesNot Available
External Links
ATC CodesC01BA02
AHFS Codes
  • 24:04.04.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe metabolism of Procainamide can be decreased when combined with Abiraterone.
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Procainamide.
AmantadineAmantadine may increase the QTc-prolonging activities of Procainamide.
AmiodaroneAmiodarone may increase the QTc-prolonging activities of Procainamide.
AmitriptylineAmitriptyline may increase the QTc-prolonging activities of Procainamide.
AmoxapineAmoxapine may increase the QTc-prolonging activities of Procainamide.
AnagrelideAnagrelide may increase the QTc-prolonging activities of Procainamide.
ApomorphineApomorphine may increase the QTc-prolonging activities of Procainamide.
ArformoterolArformoterol may increase the QTc-prolonging activities of Procainamide.
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Procainamide.
Arsenic trioxideProcainamide may increase the QTc-prolonging activities of Arsenic trioxide.
ArtemetherProcainamide may increase the QTc-prolonging activities of Artemether.
AsenapineProcainamide may increase the QTc-prolonging activities of Asenapine.
AtazanavirAtazanavir may increase the QTc-prolonging activities of Procainamide.
AtomoxetineThe metabolism of Procainamide can be decreased when combined with Atomoxetine.
AzithromycinAzithromycin may increase the QTc-prolonging activities of Procainamide.
BedaquilineBedaquiline may increase the QTc-prolonging activities of Procainamide.
BetaxololThe metabolism of Procainamide can be decreased when combined with Betaxolol.
BortezomibBortezomib may increase the QTc-prolonging activities of Procainamide.
BupropionThe metabolism of Procainamide can be decreased when combined with Bupropion.
BuserelinBuserelin may increase the QTc-prolonging activities of Procainamide.
CelecoxibThe metabolism of Procainamide can be decreased when combined with Celecoxib.
CeritinibCeritinib may increase the QTc-prolonging activities of Procainamide.
ChloroquineChloroquine may increase the QTc-prolonging activities of Procainamide.
ChlorpromazineChlorpromazine may increase the QTc-prolonging activities of Procainamide.
CholecalciferolThe metabolism of Procainamide can be decreased when combined with Cholecalciferol.
CimetidineThe metabolism of Procainamide can be decreased when combined with Cimetidine.
CinacalcetThe metabolism of Procainamide can be decreased when combined with Cinacalcet.
CiprofloxacinCiprofloxacin may increase the QTc-prolonging activities of Procainamide.
CisaprideCisapride may increase the QTc-prolonging activities of Procainamide.
CitalopramCitalopram may increase the QTc-prolonging activities of Procainamide.
ClarithromycinClarithromycin may increase the QTc-prolonging activities of Procainamide.
ClemastineThe metabolism of Procainamide can be decreased when combined with Clemastine.
ClobazamThe metabolism of Procainamide can be decreased when combined with Clobazam.
ClomipramineThe metabolism of Procainamide can be decreased when combined with Clomipramine.
ClotrimazoleThe metabolism of Procainamide can be decreased when combined with Clotrimazole.
ClozapineClozapine may increase the QTc-prolonging activities of Procainamide.
CobicistatThe serum concentration of Procainamide can be increased when it is combined with Cobicistat.
CocaineThe metabolism of Procainamide can be decreased when combined with Cocaine.
CrizotinibCrizotinib may increase the QTc-prolonging activities of Procainamide.
DabrafenibDabrafenib may increase the QTc-prolonging activities of Procainamide.
DarifenacinThe metabolism of Procainamide can be decreased when combined with Darifenacin.
DarunavirThe serum concentration of Procainamide can be increased when it is combined with Darunavir.
DasatinibDasatinib may increase the QTc-prolonging activities of Procainamide.
DegarelixDegarelix may increase the QTc-prolonging activities of Procainamide.
DelavirdineThe metabolism of Procainamide can be decreased when combined with Delavirdine.
DesfluraneDesflurane may increase the QTc-prolonging activities of Procainamide.
DesipramineThe metabolism of Procainamide can be decreased when combined with Desipramine.
DiphenhydramineThe metabolism of Procainamide can be decreased when combined with Diphenhydramine.
DisopyramideDisopyramide may increase the QTc-prolonging activities of Procainamide.
DofetilideDofetilide may increase the QTc-prolonging activities of Procainamide.
DolasetronDolasetron may increase the QTc-prolonging activities of Procainamide.
DomperidoneProcainamide may increase the QTc-prolonging activities of Domperidone.
DoxepinDoxepin may increase the QTc-prolonging activities of Procainamide.
DronedaroneProcainamide may increase the QTc-prolonging activities of Dronedarone.
DroperidolDroperidol may increase the QTc-prolonging activities of Procainamide.
DuloxetineThe metabolism of Procainamide can be decreased when combined with Duloxetine.
EliglustatProcainamide may increase the QTc-prolonging activities of Eliglustat.
EribulinEribulin may increase the QTc-prolonging activities of Procainamide.
ErythromycinErythromycin may increase the QTc-prolonging activities of Procainamide.
EscitalopramProcainamide may increase the QTc-prolonging activities of Escitalopram.
EzogabineEzogabine may increase the QTc-prolonging activities of Procainamide.
FamotidineFamotidine may increase the QTc-prolonging activities of Procainamide.
FelbamateFelbamate may increase the QTc-prolonging activities of Procainamide.
FingolimodFingolimod may increase the arrhythmogenic activities of Procainamide.
FlecainideFlecainide may increase the QTc-prolonging activities of Procainamide.
FluconazoleFluconazole may increase the QTc-prolonging activities of Procainamide.
FluoxetineFluoxetine may increase the QTc-prolonging activities of Procainamide.
FlupentixolFlupentixol may increase the QTc-prolonging activities of Procainamide.
FluvoxamineThe metabolism of Procainamide can be decreased when combined with Fluvoxamine.
FormoterolFormoterol may increase the QTc-prolonging activities of Procainamide.
FoscarnetFoscarnet may increase the QTc-prolonging activities of Procainamide.
Gadobenic acidGadobenic acid may increase the QTc-prolonging activities of Procainamide.
GalantamineGalantamine may increase the QTc-prolonging activities of Procainamide.
GemifloxacinGemifloxacin may increase the QTc-prolonging activities of Procainamide.
GoserelinGoserelin may increase the QTc-prolonging activities of Procainamide.
GranisetronGranisetron may increase the QTc-prolonging activities of Procainamide.
HaloperidolHaloperidol may increase the QTc-prolonging activities of Procainamide.
HistrelinHistrelin may increase the QTc-prolonging activities of Procainamide.
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Procainamide.
IbandronateIbandronate may increase the QTc-prolonging activities of Procainamide.
IbutilideIbutilide may increase the QTc-prolonging activities of Procainamide.
IloperidoneProcainamide may increase the QTc-prolonging activities of Iloperidone.
ImipramineThe metabolism of Procainamide can be decreased when combined with Imipramine.
IndacaterolIndacaterol may increase the QTc-prolonging activities of Procainamide.
IndapamideIndapamide may increase the QTc-prolonging activities of Procainamide.
IndinavirThe metabolism of Procainamide can be decreased when combined with Indinavir.
IsofluraneIsoflurane may increase the QTc-prolonging activities of Procainamide.
IsoniazidThe metabolism of Procainamide can be decreased when combined with Isoniazid.
IsradipineIsradipine may increase the QTc-prolonging activities of Procainamide.
ItraconazoleItraconazole may increase the QTc-prolonging activities of Procainamide.
IvabradineIvabradine may increase the QTc-prolonging activities of Procainamide.
KetoconazoleThe metabolism of Procainamide can be decreased when combined with Ketoconazole.
LamotrigineThe serum concentration of Procainamide can be increased when it is combined with Lamotrigine.
LapatinibLapatinib may increase the QTc-prolonging activities of Procainamide.
LenvatinibLenvatinib may increase the QTc-prolonging activities of Procainamide.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Procainamide.
LevofloxacinLevofloxacin may increase the QTc-prolonging activities of Procainamide.
LithiumLithium may increase the QTc-prolonging activities of Procainamide.
LopinavirProcainamide may increase the QTc-prolonging activities of Lopinavir.
LorcaserinThe metabolism of Procainamide can be decreased when combined with Lorcaserin.
LumefantrineProcainamide may increase the QTc-prolonging activities of Lumefantrine.
LurasidoneLurasidone may increase the QTc-prolonging activities of Procainamide.
MaprotilineMaprotiline may increase the QTc-prolonging activities of Procainamide.
MefloquineMefloquine may increase the QTc-prolonging activities of Procainamide.
MethadoneMethadone may increase the QTc-prolonging activities of Procainamide.
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Procainamide.
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Procainamide.
MetoprololThe metabolism of Procainamide can be decreased when combined with Metoprolol.
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Procainamide.
MifepristoneMifepristone may increase the QTc-prolonging activities of Procainamide.
MirabegronThe metabolism of Procainamide can be decreased when combined with Mirabegron.
MirtazapineMirtazapine may increase the QTc-prolonging activities of Procainamide.
MoexiprilMoexipril may increase the QTc-prolonging activities of Procainamide.
MoxifloxacinMoxifloxacin may increase the QTc-prolonging activities of Procainamide.
NelfinavirNelfinavir may increase the QTc-prolonging activities of Procainamide.
NevirapineThe metabolism of Procainamide can be decreased when combined with Nevirapine.
NicardipineThe metabolism of Procainamide can be decreased when combined with Nicardipine.
NilotinibProcainamide may increase the QTc-prolonging activities of Nilotinib.
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Procainamide.
NortriptylineNortriptyline may increase the QTc-prolonging activities of Procainamide.
OctreotideOctreotide may increase the QTc-prolonging activities of Procainamide.
OfloxacinOfloxacin may increase the QTc-prolonging activities of Procainamide.
OlanzapineOlanzapine may increase the QTc-prolonging activities of Procainamide.
OlodaterolOlodaterol may increase the QTc-prolonging activities of Procainamide.
OndansetronOndansetron may increase the QTc-prolonging activities of Procainamide.
OxytocinOxytocin may increase the QTc-prolonging activities of Procainamide.
PaliperidoneProcainamide may increase the QTc-prolonging activities of Paliperidone.
PanobinostatPanobinostat may increase the QTc-prolonging activities of Procainamide.
ParoxetineParoxetine may increase the QTc-prolonging activities of Procainamide.
PasireotidePasireotide may increase the QTc-prolonging activities of Procainamide.
PazopanibPazopanib may increase the QTc-prolonging activities of Procainamide.
Peginterferon alfa-2bThe serum concentration of Procainamide can be decreased when it is combined with Peginterferon alfa-2b.
PentamidinePentamidine may increase the QTc-prolonging activities of Procainamide.
PerflutrenPerflutren may increase the QTc-prolonging activities of Procainamide.
PimozideProcainamide may increase the QTc-prolonging activities of Pimozide.
PosaconazolePosaconazole may increase the QTc-prolonging activities of Procainamide.
PrimaquinePrimaquine may increase the QTc-prolonging activities of Procainamide.
PromazinePromazine may increase the QTc-prolonging activities of Procainamide.
PromethazinePromethazine may increase the QTc-prolonging activities of Procainamide.
PropafenonePropafenone may increase the arrhythmogenic activities of Procainamide.
PropofolPropofol may increase the QTc-prolonging activities of Procainamide.
ProtriptylineProtriptyline may increase the QTc-prolonging activities of Procainamide.
QuetiapineProcainamide may increase the QTc-prolonging activities of Quetiapine.
QuinidineQuinidine may increase the QTc-prolonging activities of Procainamide.
QuinineQuinine may increase the QTc-prolonging activities of Procainamide.
RanitidineThe serum concentration of Procainamide can be increased when it is combined with Ranitidine.
RanolazineThe metabolism of Procainamide can be decreased when combined with Ranolazine.
RilpivirineRilpivirine may increase the QTc-prolonging activities of Procainamide.
RisperidoneRisperidone may increase the QTc-prolonging activities of Procainamide.
RitonavirRitonavir may increase the QTc-prolonging activities of Procainamide.
RolapitantThe metabolism of Procainamide can be decreased when combined with Rolapitant.
RopiniroleThe metabolism of Procainamide can be decreased when combined with Ropinirole.
SalbutamolSalbutamol may increase the QTc-prolonging activities of Procainamide.
SalmeterolSalmeterol may increase the QTc-prolonging activities of Procainamide.
SaquinavirSaquinavir may increase the QTc-prolonging activities of Procainamide.
SertralineThe metabolism of Procainamide can be decreased when combined with Sertraline.
SevofluraneSevoflurane may increase the QTc-prolonging activities of Procainamide.
SolifenacinSolifenacin may increase the QTc-prolonging activities of Procainamide.
SorafenibSorafenib may increase the QTc-prolonging activities of Procainamide.
SotalolSotalol may increase the QTc-prolonging activities of Procainamide.
StiripentolThe metabolism of Procainamide can be decreased when combined with Stiripentol.
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Procainamide.
SulfisoxazoleSulfisoxazole may increase the QTc-prolonging activities of Procainamide.
SulpirideThe risk or severity of adverse effects can be increased when Procainamide is combined with Sulpiride.
SunitinibSunitinib may increase the QTc-prolonging activities of Procainamide.
TamoxifenTamoxifen may increase the QTc-prolonging activities of Procainamide.
TelavancinTelavancin may increase the QTc-prolonging activities of Procainamide.
TelithromycinTelithromycin may increase the QTc-prolonging activities of Procainamide.
TerbinafineThe metabolism of Procainamide can be decreased when combined with Terbinafine.
TerbutalineTerbutaline may increase the QTc-prolonging activities of Procainamide.
TetrabenazineProcainamide may increase the QTc-prolonging activities of Tetrabenazine.
ThioridazineThioridazine may increase the QTc-prolonging activities of Procainamide.
ThiothixeneThiothixene may increase the QTc-prolonging activities of Procainamide.
TiclopidineThe metabolism of Procainamide can be decreased when combined with Ticlopidine.
TipranavirThe metabolism of Procainamide can be decreased when combined with Tipranavir.
TizanidineTizanidine may increase the QTc-prolonging activities of Procainamide.
TolterodineTolterodine may increase the QTc-prolonging activities of Procainamide.
ToremifeneToremifene may increase the QTc-prolonging activities of Procainamide.
TranylcypromineThe metabolism of Procainamide can be decreased when combined with Tranylcypromine.
TrazodoneTrazodone may increase the QTc-prolonging activities of Procainamide.
TreprostinilTreprostinil may increase the QTc-prolonging activities of Procainamide.
TrimethoprimThe serum concentration of the active metabolites of Procainamide can be increased when Procainamide is used in combination with Trimethoprim.
TrimipramineTrimipramine may increase the QTc-prolonging activities of Procainamide.
TriptorelinTriptorelin may increase the QTc-prolonging activities of Procainamide.
VandetanibProcainamide may increase the QTc-prolonging activities of Vandetanib.
VardenafilVardenafil may increase the QTc-prolonging activities of Procainamide.
VemurafenibProcainamide may increase the QTc-prolonging activities of Vemurafenib.
VenlafaxineThe metabolism of Procainamide can be decreased when combined with Venlafaxine.
VilanterolVilanterol may increase the QTc-prolonging activities of Procainamide.
VoriconazoleVoriconazole may increase the QTc-prolonging activities of Procainamide.
VorinostatVorinostat may increase the QTc-prolonging activities of Procainamide.
ZiprasidoneZiprasidone may increase the QTc-prolonging activities of Procainamide.
ZuclopenthixolProcainamide may increase the QTc-prolonging activities of Zuclopenthixol.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
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. Weiss R, Barmada MM, Nguyen T, Seibel JS, Cavlovich D, Kornblit CA, Angelilli A, Villanueva F, McNamara DM, London B: Clinical and molecular heterogeneity in the Brugada syndrome: a novel gene locus on chromosome 3. Circulation. 2002 Feb 12;105(6):707-13. [PubMed:11839626 ]
  2. Brugada R, Brugada J, Antzelevitch C, Kirsch GE, Potenza D, Towbin JA, Brugada P: Sodium channel blockers identify risk for sudden death in patients with ST-segment elevation and right bundle branch block but structurally normal hearts. Circulation. 2000 Feb 8;101(5):510-5. [PubMed:10662748 ]
  3. Chen SM, Kuo CT, Lin KH, Chiang FT: Brugada syndrome without mutation of the cardiac sodium channel gene in a Taiwanese patient. J Formos Med Assoc. 2000 Nov;99(11):860-2. [PubMed:11155778 ]
  4. Brugada J, Brugada R, Brugada P: [Brugada syndrome]. Arch Mal Coeur Vaiss. 1999 Jul;92(7):847-50. [PubMed:10443304 ]
  5. Brugada J, Brugada P, Brugada R: The syndrome of right bundle branch block ST segment elevation in V1 to V3 and sudden death--the Brugada syndrome. Europace. 1999 Jul;1(3):156-66. [PubMed:11225790 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other
General Function:
Zinc ion binding
Specific Function:
Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns ...
Gene Name:
DNMT1
Uniprot ID:
P26358
Molecular Weight:
183163.635 Da
References
  1. Oelke K, Lu Q, Richardson D, Wu A, Deng C, Hanash S, Richardson B: Overexpression of CD70 and overstimulation of IgG synthesis by lupus T cells and T cells treated with DNA methylation inhibitors. Arthritis Rheum. 2004 Jun;50(6):1850-60. [PubMed:15188362 ]
  2. Januchowski R, Jagodzinski PP: Effect of 5-azacytidine and procainamide on CD3-zeta chain expression in Jurkat T cells. Biomed Pharmacother. 2005 Apr;59(3):122-6. [PubMed:15795105 ]
  3. Lee BH, Yegnasubramanian S, Lin X, Nelson WG: Procainamide is a specific inhibitor of DNA methyltransferase 1. J Biol Chem. 2005 Dec 9;280(49):40749-56. Epub 2005 Oct 17. [PubMed:16230360 ]
  4. Scheinbart LS, Johnson MA, Gross LA, Edelstein SR, Richardson BC: Procainamide inhibits DNA methyltransferase in a human T cell line. J Rheumatol. 1991 Apr;18(4):530-4. [PubMed:2066944 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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. Lessard E, Hamelin BA, Labbe L, O'Hara G, Belanger PM, Turgeon J: Involvement of CYP2D6 activity in the N-oxidation of procainamide in man. Pharmacogenetics. 1999 Dec;9(6):683-96. [PubMed:10634131 ]
  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:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Bailey DN: Amitriptyline and procainamide inhibition of cocaine and cocaethylene degradation in human serum in vitro. J Anal Toxicol. 1999 Mar-Apr;23(2):99-102. [PubMed:10192412 ]
  2. Page JD, Wilson IB, Silman I: Butyrylcholinesterase: inhibition by arsenite, fluoride, and other ligands, cooperativity in binding. Mol Pharmacol. 1985 Apr;27(4):437-43. [PubMed:3982389 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
  2. Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [PubMed:9260930 ]
  3. Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
  4. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
  5. Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515 ]
  6. Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376 ]
  7. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]
  2. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
  3. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
  4. Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
  5. Green RM, Lo K, Sterritt C, Beier DR: Cloning and functional expression of a mouse liver organic cation transporter. Hepatology. 1999 May;29(5):1556-62. [PubMed:10216142 ]
  6. Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. [PubMed:9195965 ]
  7. Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515 ]
  8. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
  9. Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. [PubMed:7990927 ]
  10. Ishiguro N, Saito A, Yokoyama K, Morikawa M, Igarashi T, Tamai I: Transport of the dopamine D2 agonist pramipexole by rat organic cation transporters OCT1 and OCT2 in kidney. Drug Metab Dispos. 2005 Apr;33(4):495-9. Epub 2005 Jan 7. [PubMed:15640376 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [PubMed:10966924 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [PubMed:9618255 ]
  2. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]
  3. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]
  4. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
  2. Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23