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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 release250 mgOralErfa Canada 2012 Inc1985-12-31Not applicableCanada
Procan SRTablet, extended release500 mgOralErfa Canada 2012 Inc1985-12-312015-06-05Canada
Procan SRTablet, extended release750 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 release500 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
614-39-1
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 KeyREQCZEXYDRLIBE-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
Pharmacology
IndicationFor the treatment of life-threatening ventricular arrhythmias.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium channel protein type 5 subunit alphaProteinunknown
inhibitor
HumanQ14524 details
DNA (cytosine-5)-methyltransferase 1Proteinunknown
other
HumanP26358 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Procainamide can be increased when it is combined with Abiraterone.Approved
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
AmantadineAmantadine may increase the QTc-prolonging activities of Procainamide.Approved
AmiodaroneAmiodarone may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
AmitriptylineAmitriptyline may increase the QTc-prolonging activities of Procainamide.Approved
AmoxapineAmoxapine may increase the QTc-prolonging activities of Procainamide.Approved
AnagrelideAnagrelide may increase the QTc-prolonging activities of Procainamide.Approved
ApomorphineApomorphine may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
ArformoterolArformoterol may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
Arsenic trioxideProcainamide may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherProcainamide may increase the QTc-prolonging activities of Artemether.Approved
AsenapineProcainamide may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirAtazanavir may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
AtomoxetineAtomoxetine may increase the QTc-prolonging activities of Procainamide.Approved
Atracurium besylateProcainamide may increase the neuromuscular blocking activities of Atracurium besylate.Approved
AzithromycinAzithromycin may increase the QTc-prolonging activities of Procainamide.Approved
BedaquilineBedaquiline may increase the QTc-prolonging activities of Procainamide.Approved
BetaxololThe metabolism of Procainamide can be decreased when combined with Betaxolol.Approved
BortezomibBortezomib may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
BupropionThe metabolism of Procainamide can be decreased when combined with Bupropion.Approved
BuserelinBuserelin may increase the QTc-prolonging activities of Procainamide.Approved
CelecoxibThe metabolism of Procainamide can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibCeritinib may increase the QTc-prolonging activities of Procainamide.Approved
ChloroquineChloroquine may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
ChlorpromazineChlorpromazine may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
CholecalciferolThe metabolism of Procainamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe serum concentration of Procainamide can be increased when it is combined with Cimetidine.Approved
CinacalcetThe metabolism of Procainamide can be decreased when combined with Cinacalcet.Approved
CiprofloxacinCiprofloxacin may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
CisaprideCisapride may increase the QTc-prolonging activities of Procainamide.Approved, Investigational, Withdrawn
Cisatracurium besylateProcainamide may increase the neuromuscular blocking activities of Cisatracurium besylate.Approved
CitalopramCitalopram may increase the QTc-prolonging activities of Procainamide.Approved
ClarithromycinClarithromycin may increase the QTc-prolonging activities of Procainamide.Approved
ClemastineThe metabolism of Procainamide can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Procainamide can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineClomipramine may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
ClotrimazoleThe metabolism of Procainamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineClozapine may increase the QTc-prolonging activities of Procainamide.Approved
CobicistatThe serum concentration of Procainamide can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Procainamide can be decreased when combined with Cocaine.Approved, Illicit
CrizotinibCrizotinib may increase the QTc-prolonging activities of Procainamide.Approved
DabrafenibDabrafenib may increase the QTc-prolonging activities of Procainamide.Approved
DarifenacinThe metabolism of Procainamide can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Procainamide can be increased when it is combined with Darunavir.Approved
DasatinibDasatinib may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
DecamethoniumProcainamide may increase the neuromuscular blocking activities of Decamethonium.Approved
DegarelixDegarelix may increase the QTc-prolonging activities of Procainamide.Approved
DelavirdineThe metabolism of Procainamide can be decreased when combined with Delavirdine.Approved
DesfluraneDesflurane may increase the QTc-prolonging activities of Procainamide.Approved
DesipramineDesipramine may increase the QTc-prolonging activities of Procainamide.Approved
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Procainamide.Approved
DisopyramideDisopyramide may increase the QTc-prolonging activities of Procainamide.Approved
DofetilideDofetilide may increase the QTc-prolonging activities of Procainamide.Approved
DolasetronDolasetron may increase the QTc-prolonging activities of Procainamide.Approved
Domoic AcidProcainamide may increase the neuromuscular blocking activities of Domoic Acid.Experimental
DomperidoneProcainamide may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
Doxacurium chlorideProcainamide may increase the neuromuscular blocking activities of Doxacurium chloride.Approved
DoxepinDoxepin may increase the QTc-prolonging activities of Procainamide.Approved
DronedaroneProcainamide may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolDroperidol may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
DuloxetineThe metabolism of Procainamide can be decreased when combined with Duloxetine.Approved
EliglustatProcainamide may increase the QTc-prolonging activities of Eliglustat.Approved
EribulinEribulin may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
ErythromycinErythromycin may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
EscitalopramProcainamide may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
EzogabineEzogabine may increase the QTc-prolonging activities of Procainamide.Approved
FamotidineFamotidine may increase the QTc-prolonging activities of Procainamide.Approved
FelbamateFelbamate may increase the QTc-prolonging activities of Procainamide.Approved
FingolimodFingolimod may increase the arrhythmogenic activities of Procainamide.Approved, Investigational
FlecainideFlecainide may increase the QTc-prolonging activities of Procainamide.Approved, Withdrawn
FluconazoleFluconazole may increase the QTc-prolonging activities of Procainamide.Approved
FluoxetineFluoxetine may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
FlupentixolFlupentixol may increase the QTc-prolonging activities of Procainamide.Approved, Withdrawn
FluvoxamineThe metabolism of Procainamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolFormoterol may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
FoscarnetFoscarnet may increase the QTc-prolonging activities of Procainamide.Approved
Gadobenic acidGadobenic acid may increase the QTc-prolonging activities of Procainamide.Approved
GalantamineGalantamine may increase the QTc-prolonging activities of Procainamide.Approved
Gallamine TriethiodideProcainamide may increase the neuromuscular blocking activities of Gallamine Triethiodide.Approved
GemifloxacinGemifloxacin may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
GoserelinGoserelin may increase the QTc-prolonging activities of Procainamide.Approved
GranisetronGranisetron may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
HaloperidolHaloperidol may increase the QTc-prolonging activities of Procainamide.Approved
HistrelinHistrelin may increase the QTc-prolonging activities of Procainamide.Approved
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Procainamide.Approved
IbandronateIbandronate may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
IbutilideIbutilide may increase the QTc-prolonging activities of Procainamide.Approved
IloperidoneProcainamide may increase the QTc-prolonging activities of Iloperidone.Approved
ImipramineImipramine may increase the QTc-prolonging activities of Procainamide.Approved
IndacaterolIndacaterol may increase the QTc-prolonging activities of Procainamide.Approved
IndapamideIndapamide may increase the QTc-prolonging activities of Procainamide.Approved
IndinavirThe metabolism of Procainamide can be decreased when combined with Indinavir.Approved
IsofluraneIsoflurane may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
IsoniazidThe metabolism of Procainamide can be decreased when combined with Isoniazid.Approved
IsradipineIsradipine may increase the QTc-prolonging activities of Procainamide.Approved
ItraconazoleItraconazole may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
IvabradineIvabradine may increase the QTc-prolonging activities of Procainamide.Approved
KetoconazoleKetoconazole may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
LamotrigineThe serum concentration of Procainamide can be increased when it is combined with Lamotrigine.Approved, Investigational
LapatinibLapatinib may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
LenvatinibLenvatinib may increase the QTc-prolonging activities of Procainamide.Approved
LeuprolideLeuprolide may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
LevofloxacinLevofloxacin may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
LithiumLithium may increase the QTc-prolonging activities of Procainamide.Approved
LopinavirProcainamide may increase the QTc-prolonging activities of Lopinavir.Approved
LorcaserinThe metabolism of Procainamide can be decreased when combined with Lorcaserin.Approved
LumefantrineProcainamide may increase the QTc-prolonging activities of Lumefantrine.Approved
LurasidoneLurasidone may increase the QTc-prolonging activities of Procainamide.Approved
MaprotilineMaprotiline may increase the QTc-prolonging activities of Procainamide.Approved
MefloquineMefloquine may increase the QTc-prolonging activities of Procainamide.Approved
MethadoneMethadone may increase the QTc-prolonging activities of Procainamide.Approved
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Procainamide.Approved
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
MetocurineProcainamide may increase the neuromuscular blocking activities of Metocurine.Approved
Metocurine IodideProcainamide may increase the neuromuscular blocking activities of Metocurine Iodide.Withdrawn
MetoprololThe metabolism of Procainamide can be decreased when combined with Metoprolol.Approved, Investigational
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Procainamide.Approved
MifepristoneMifepristone may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
MirabegronMirabegron may increase the QTc-prolonging activities of Procainamide.Approved
MirtazapineMirtazapine may increase the QTc-prolonging activities of Procainamide.Approved
MivacuriumProcainamide may increase the neuromuscular blocking activities of Mivacurium.Approved
MoexiprilMoexipril may increase the QTc-prolonging activities of Procainamide.Approved
MoxifloxacinMoxifloxacin may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
NelfinavirNelfinavir may increase the QTc-prolonging activities of Procainamide.Approved
NeosaxitoxinProcainamide may increase the neuromuscular blocking activities of Neosaxitoxin.Investigational
NevirapineThe metabolism of Procainamide can be decreased when combined with Nevirapine.Approved
NicardipineNicardipine may increase the QTc-prolonging activities of Procainamide.Approved
NilotinibProcainamide may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Procainamide.Approved
NortriptylineNortriptyline may increase the QTc-prolonging activities of Procainamide.Approved
OctreotideOctreotide may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
OfloxacinOfloxacin may increase the QTc-prolonging activities of Procainamide.Approved
OlanzapineOlanzapine may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
OlodaterolOlodaterol may increase the QTc-prolonging activities of Procainamide.Approved
OndansetronOndansetron may increase the QTc-prolonging activities of Procainamide.Approved
OxytocinOxytocin may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
PaliperidoneProcainamide may increase the QTc-prolonging activities of Paliperidone.Approved
PancuroniumProcainamide may increase the neuromuscular blocking activities of Pancuronium.Approved
PanobinostatThe serum concentration of Procainamide can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineParoxetine may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
PasireotidePasireotide may increase the QTc-prolonging activities of Procainamide.Approved
PazopanibPazopanib may increase the QTc-prolonging activities of Procainamide.Approved
Peginterferon alfa-2bThe serum concentration of Procainamide can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentamidinePentamidine may increase the QTc-prolonging activities of Procainamide.Approved
PerflutrenPerflutren may increase the QTc-prolonging activities of Procainamide.Approved
PimozideProcainamide may increase the QTc-prolonging activities of Pimozide.Approved
PipecuroniumProcainamide may increase the neuromuscular blocking activities of Pipecuronium.Approved
PosaconazolePosaconazole may increase the QTc-prolonging activities of Procainamide.Approved, Investigational, Vet Approved
PrimaquinePrimaquine may increase the QTc-prolonging activities of Procainamide.Approved
PromazinePromazine may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
PromethazinePromethazine may increase the QTc-prolonging activities of Procainamide.Approved
PropafenonePropafenone may increase the arrhythmogenic activities of Procainamide.Approved
PropofolPropofol may increase the QTc-prolonging activities of Procainamide.Approved, Investigational, Vet Approved
ProtriptylineProtriptyline may increase the QTc-prolonging activities of Procainamide.Approved
PyrantelProcainamide may increase the neuromuscular blocking activities of Pyrantel.Approved, Vet Approved
QuetiapineProcainamide may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineQuinidine may increase the QTc-prolonging activities of Procainamide.Approved
QuinineQuinine may increase the QTc-prolonging activities of Procainamide.Approved
RanitidineThe serum concentration of Procainamide can be increased when it is combined with Ranitidine.Approved
RanolazineRanolazine may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
RapacuroniumProcainamide may increase the neuromuscular blocking activities of Rapacuronium.Withdrawn
RilpivirineRilpivirine may increase the QTc-prolonging activities of Procainamide.Approved
RisperidoneRisperidone may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
RitonavirRitonavir may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
RocuroniumProcainamide may increase the neuromuscular blocking activities of Rocuronium.Approved
RolapitantThe metabolism of Procainamide can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Procainamide can be decreased when combined with Ropinirole.Approved, Investigational
SalbutamolSalbutamol may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
SalmeterolSalmeterol may increase the QTc-prolonging activities of Procainamide.Approved
SaquinavirSaquinavir may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
SertralineSertraline may increase the QTc-prolonging activities of Procainamide.Approved
SevofluraneSevoflurane may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
SolifenacinSolifenacin may increase the QTc-prolonging activities of Procainamide.Approved
SorafenibSorafenib may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
SotalolSotalol may increase the QTc-prolonging activities of Procainamide.Approved
StiripentolThe metabolism of Procainamide can be decreased when combined with Stiripentol.Approved
SuccinylcholineProcainamide may increase the neuromuscular blocking activities of Succinylcholine.Approved
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Procainamide.Approved
SulfisoxazoleSulfisoxazole may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
SulpirideThe risk or severity of adverse effects can be increased when Procainamide is combined with Sulpiride.Approved
SunitinibSunitinib may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
TamoxifenTamoxifen may increase the QTc-prolonging activities of Procainamide.Approved
TelavancinTelavancin may increase the QTc-prolonging activities of Procainamide.Approved
TelithromycinTelithromycin may increase the QTc-prolonging activities of Procainamide.Approved
TerbinafineThe metabolism of Procainamide can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerbutalineTerbutaline may increase the QTc-prolonging activities of Procainamide.Approved
TetrabenazineProcainamide may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThioridazineThioridazine may increase the QTc-prolonging activities of Procainamide.Approved
ThiothixeneThiothixene may increase the QTc-prolonging activities of Procainamide.Approved
TiclopidineThe metabolism of Procainamide can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Procainamide can be decreased when combined with Tipranavir.Approved, Investigational
TizanidineTizanidine may increase the QTc-prolonging activities of Procainamide.Approved
TolterodineTolterodine may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
ToremifeneToremifene may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
TranylcypromineThe metabolism of Procainamide can be decreased when combined with Tranylcypromine.Approved
TrazodoneTrazodone may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
TreprostinilTreprostinil may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
TrimethoprimThe serum concentration of the active metabolites of Procainamide can be increased when Procainamide is used in combination with Trimethoprim.Approved, Vet Approved
TrimipramineTrimipramine may increase the QTc-prolonging activities of Procainamide.Approved
TriptorelinTriptorelin may increase the QTc-prolonging activities of Procainamide.Approved, Vet Approved
TubocurarineProcainamide may increase the neuromuscular blocking activities of Tubocurarine.Approved
VandetanibProcainamide may increase the QTc-prolonging activities of Vandetanib.Approved
VardenafilVardenafil may increase the QTc-prolonging activities of Procainamide.Approved
VecuroniumProcainamide may increase the neuromuscular blocking activities of Vecuronium.Approved
VemurafenibProcainamide may increase the QTc-prolonging activities of Vemurafenib.Approved
VenlafaxineVenlafaxine may increase the QTc-prolonging activities of Procainamide.Approved
VilanterolVilanterol may increase the QTc-prolonging activities of Procainamide.Approved
VoriconazoleVoriconazole may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
VorinostatVorinostat may increase the QTc-prolonging activities of Procainamide.Approved, Investigational
ZiprasidoneZiprasidone may increase the QTc-prolonging activities of Procainamide.Approved
ZuclopenthixolProcainamide may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.
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)
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 releaseOral250 mg
Tablet, extended releaseOral500 mg
Tablet, extended releaseOral750 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
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

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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:11