Procainamide - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (3)Enzymes (2)Transporters (5)

Targets (3)Enzymes (2)Transporters (5)Biointeractions (10)

Identification

Name

Procainamide

Accession Number

DB01035 (APRD00509)

Type

Small Molecule

Groups

Approved

Description

A derivative of procaine with less CNS action. [PubChem]

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Biocoryl

p-Amino-N-(2-diethylaminoethyl)benzamide

p-Aminobenzoic diethylaminoethylamide

Procainamida

Procainamide

Procainamidum

External IDs

NSC-27461

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Procainamide Hydrochloride	SI4064O0LX	614-39-1	ABTXGJFUQRCPNH-UHFFFAOYSA-N	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Procainamide Hydrochloride Inj. USP	Solution	100 mg	Intramuscular; Intravenous	Sandoz Canada Incorporated	1995-12-31	Not applicable	Canada
Procainamide-250 Cap 250mg	Capsule	250 mg	Oral	Pro Doc Limitee	1987-12-31	2000-07-31	Canada
Procainamide-375 Cap 375mg	Capsule	375 mg	Oral	Pro Doc Limitee	1987-12-31	2000-07-31	Canada
Procainamide-500 Cap 500mg	Capsule	500 mg	Oral	Pro Doc Limitee	1987-12-31	2000-07-31	Canada
Procan SR	Tablet, extended release	750 mg	Oral	Erfa Canada 2012 Inc	1985-12-31	2015-06-05	Canada
Procan SR	Tablet, extended release	250 mg	Oral	Erfa Canada 2012 Inc	1985-12-31	Not applicable	Canada
Procan SR	Tablet, extended release	500 mg	Oral	Erfa Canada 2012 Inc	1985-12-31	2015-06-05	Canada
Pronestyl Cap 250mg	Capsule	250 mg	Oral	Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.	1955-12-31	2002-07-30	Canada
Pronestyl Cap 375mg	Capsule	375 mg	Oral	Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.	1973-12-31	2002-07-30	Canada
Pronestyl Cap 500mg	Capsule	500 mg	Oral	Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.	1976-12-31	2002-07-30	Canada
Pronestyl Inj 100mg/ml	Liquid	100 mg	Intramuscular; Intravenous	Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.	1955-12-31	2002-07-30	Canada
Pronestyl-SR Tab 500mg	Tablet, extended release	500 mg	Oral	Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.	1984-12-31	2005-08-01	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-procainamide Cap 250mg	Capsule	250 mg	Oral	Apotex Corporation	1986-12-31	Not applicable	Canada
Apo-procainamide Cap 375mg	Capsule	375 g	Oral	Apotex Corporation	1986-12-31	Not applicable	Canada
Apo-procainamide Cap 500mg	Capsule	500 mg	Oral	Apotex Corporation	1986-12-31	Not applicable	Canada
Procainamide Hydrochloride	Injection, solution	500 mg/mL	Intramuscular; Intravenous	Cardinal Health	1986-02-12	Not applicable	US
Procainamide Hydrochloride	Injection, solution	500 mg/mL	Intramuscular; Intravenous	Hospira, Inc.	1986-02-12	Not applicable	US
Procainamide Hydrochloride	Injection	100 mg/mL	Intramuscular; Intravenous	International Medication Systems, Limited	2016-12-21	Not applicable	US
Procainamide Hydrochloride	Injection, solution	100 mg/mL	Intramuscular; Intravenous	Cardinal Health	2011-07-08	Not applicable	US
Procainamide Hydrochloride	Injection, solution	100 mg/mL	Intramuscular; Intravenous	Hospira, Inc.	1986-02-12	Not applicable	US
Procainamide Hydrochloride	Injection, solution	100 mg/mL	Intramuscular; Intravenous	Mc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation	2010-02-01	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Biocoryl	Not Available
Procan	Not Available
Procanbid	Not Available
Procapan	Not Available
Pronestyl	Not Available

Brand mixtures

Not Available

Categories

UNII

L39WTC366D

CAS number

51-06-9

Weight

Average: 235.3253
Monoisotopic: 235.168462309

Chemical Formula

C₁₃H₂₁N₃O

InChI Key

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

Pharmacology

Indication

For the treatment of life-threatening ventricular arrhythmias.

Structured Indications

Pharmacodynamics

Procainamide 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 action

Procainamide 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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Sodium channel protein type 5 subunit alpha	Protein	unknown	inhibitor	Human	Q14524	details
DNA (cytosine-5)-methyltransferase 1	Protein	unknown	other	Human	P26358	details
Potassium voltage-gated channel subfamily H member 2	Protein	unknown	inhibitor	Human	Q12809	details

Absorption

75 to 95%

Volume of distribution

2 L/kg

Protein binding

15 to 20%

Metabolism

Hepatic

Substrate	Enzymes	Product
Procainamide	Cytochrome P450 2D6	N-Acetyl-3-hydroxyprocainamide	Details

Route of elimination

Trace 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

Clearance

Not Available

Toxicity

LD₅₀=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

Pathway	Category	SMPDB ID
Procainamide (Antiarrhythmic) Action Pathway	Drug action	SMP00324

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Abiraterone	The serum concentration of Procainamide can be increased when it is combined with Abiraterone.	Approved
Alfuzosin	Alfuzosin may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Amantadine	Amantadine may increase the QTc-prolonging activities of Procainamide.	Approved
Amiodarone	Amiodarone may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Amitriptyline	Amitriptyline may increase the QTc-prolonging activities of Procainamide.	Approved
Amoxapine	Amoxapine may increase the QTc-prolonging activities of Procainamide.	Approved
Anagrelide	Anagrelide may increase the QTc-prolonging activities of Procainamide.	Approved
Apomorphine	Apomorphine may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Arformoterol	Arformoterol may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Aripiprazole	Aripiprazole may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Arsenic trioxide	Procainamide may increase the QTc-prolonging activities of Arsenic trioxide.	Approved, Investigational
Artemether	Procainamide may increase the QTc-prolonging activities of Artemether.	Approved
Asenapine	Procainamide may increase the QTc-prolonging activities of Asenapine.	Approved
Atazanavir	Atazanavir may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Atomoxetine	Atomoxetine may increase the QTc-prolonging activities of Procainamide.	Approved
Atracurium besylate	Procainamide may increase the neuromuscular blocking activities of Atracurium besylate.	Approved
Azithromycin	Azithromycin may increase the QTc-prolonging activities of Procainamide.	Approved
Bedaquiline	Bedaquiline may increase the QTc-prolonging activities of Procainamide.	Approved
Betaxolol	The metabolism of Procainamide can be decreased when combined with Betaxolol.	Approved
Bortezomib	Bortezomib may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Bupropion	The metabolism of Procainamide can be decreased when combined with Bupropion.	Approved
Buserelin	Buserelin may increase the QTc-prolonging activities of Procainamide.	Approved
Celecoxib	The metabolism of Procainamide can be decreased when combined with Celecoxib.	Approved, Investigational
Ceritinib	Ceritinib may increase the QTc-prolonging activities of Procainamide.	Approved
Chloroquine	Chloroquine may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Chlorpromazine	Chlorpromazine may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Cholecalciferol	The metabolism of Procainamide can be decreased when combined with Cholecalciferol.	Approved, Nutraceutical
Cimetidine	The serum concentration of Procainamide can be increased when it is combined with Cimetidine.	Approved
Cinacalcet	The metabolism of Procainamide can be decreased when combined with Cinacalcet.	Approved
Ciprofloxacin	Ciprofloxacin may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Cisapride	Cisapride may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational, Withdrawn
Cisatracurium besylate	Procainamide may increase the neuromuscular blocking activities of Cisatracurium besylate.	Approved
Citalopram	Citalopram may increase the QTc-prolonging activities of Procainamide.	Approved
Clarithromycin	Clarithromycin may increase the QTc-prolonging activities of Procainamide.	Approved
Clemastine	The metabolism of Procainamide can be decreased when combined with Clemastine.	Approved
Clobazam	The metabolism of Procainamide can be decreased when combined with Clobazam.	Approved, Illicit
Clomipramine	Clomipramine may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Clotrimazole	The metabolism of Procainamide can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Clozapine	Clozapine may increase the QTc-prolonging activities of Procainamide.	Approved
Cobicistat	The serum concentration of Procainamide can be increased when it is combined with Cobicistat.	Approved
Cocaine	The metabolism of Procainamide can be decreased when combined with Cocaine.	Approved, Illicit
Crizotinib	Crizotinib may increase the QTc-prolonging activities of Procainamide.	Approved
Dabrafenib	Dabrafenib may increase the QTc-prolonging activities of Procainamide.	Approved
Darifenacin	The metabolism of Procainamide can be decreased when combined with Darifenacin.	Approved, Investigational
Darunavir	The serum concentration of Procainamide can be increased when it is combined with Darunavir.	Approved
Dasatinib	Dasatinib may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Decamethonium	Procainamide may increase the neuromuscular blocking activities of Decamethonium.	Approved
Degarelix	Degarelix may increase the QTc-prolonging activities of Procainamide.	Approved
Delavirdine	The metabolism of Procainamide can be decreased when combined with Delavirdine.	Approved
Desflurane	Desflurane may increase the QTc-prolonging activities of Procainamide.	Approved
Desipramine	Desipramine may increase the QTc-prolonging activities of Procainamide.	Approved
Diphenhydramine	Diphenhydramine may increase the QTc-prolonging activities of Procainamide.	Approved
Disopyramide	Disopyramide may increase the QTc-prolonging activities of Procainamide.	Approved
Dofetilide	Dofetilide may increase the QTc-prolonging activities of Procainamide.	Approved
Dolasetron	Dolasetron may increase the QTc-prolonging activities of Procainamide.	Approved
Domoic Acid	Procainamide may increase the neuromuscular blocking activities of Domoic Acid.	Experimental
Domperidone	Procainamide may increase the QTc-prolonging activities of Domperidone.	Approved, Investigational, Vet Approved
Doxacurium chloride	Procainamide may increase the neuromuscular blocking activities of Doxacurium chloride.	Approved
Doxepin	Doxepin may increase the QTc-prolonging activities of Procainamide.	Approved
Dronedarone	Procainamide may increase the QTc-prolonging activities of Dronedarone.	Approved
Droperidol	Droperidol may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Duloxetine	The metabolism of Procainamide can be decreased when combined with Duloxetine.	Approved
Eliglustat	Procainamide may increase the QTc-prolonging activities of Eliglustat.	Approved
Eribulin	Eribulin may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Erythromycin	Erythromycin may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Escitalopram	Procainamide may increase the QTc-prolonging activities of Escitalopram.	Approved, Investigational
Ezogabine	Ezogabine may increase the QTc-prolonging activities of Procainamide.	Approved
Famotidine	Famotidine may increase the QTc-prolonging activities of Procainamide.	Approved
Felbamate	Felbamate may increase the QTc-prolonging activities of Procainamide.	Approved
Fingolimod	Fingolimod may increase the arrhythmogenic activities of Procainamide.	Approved, Investigational
Flecainide	Flecainide may increase the QTc-prolonging activities of Procainamide.	Approved, Withdrawn
Fluconazole	Fluconazole may increase the QTc-prolonging activities of Procainamide.	Approved
Fluoxetine	Fluoxetine may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Flupentixol	Flupentixol may increase the QTc-prolonging activities of Procainamide.	Approved, Withdrawn
Fluvoxamine	The metabolism of Procainamide can be decreased when combined with Fluvoxamine.	Approved, Investigational
Formoterol	Formoterol may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Foscarnet	Foscarnet may increase the QTc-prolonging activities of Procainamide.	Approved
Gadobenic acid	Gadobenic acid may increase the QTc-prolonging activities of Procainamide.	Approved
Galantamine	Galantamine may increase the QTc-prolonging activities of Procainamide.	Approved
Gallamine Triethiodide	Procainamide may increase the neuromuscular blocking activities of Gallamine Triethiodide.	Approved
Gemifloxacin	Gemifloxacin may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Goserelin	Goserelin may increase the QTc-prolonging activities of Procainamide.	Approved
Granisetron	Granisetron may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Haloperidol	Haloperidol may increase the QTc-prolonging activities of Procainamide.	Approved
Histrelin	Histrelin may increase the QTc-prolonging activities of Procainamide.	Approved
Hydroxyzine	Hydroxyzine may increase the QTc-prolonging activities of Procainamide.	Approved
Ibandronate	Ibandronate may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Ibutilide	Ibutilide may increase the QTc-prolonging activities of Procainamide.	Approved
Iloperidone	Procainamide may increase the QTc-prolonging activities of Iloperidone.	Approved
Imipramine	Imipramine may increase the QTc-prolonging activities of Procainamide.	Approved
Indacaterol	Indacaterol may increase the QTc-prolonging activities of Procainamide.	Approved
Indapamide	Indapamide may increase the QTc-prolonging activities of Procainamide.	Approved
Indinavir	The metabolism of Procainamide can be decreased when combined with Indinavir.	Approved
Isoflurane	Isoflurane may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Isoniazid	The metabolism of Procainamide can be decreased when combined with Isoniazid.	Approved
Isradipine	Isradipine may increase the QTc-prolonging activities of Procainamide.	Approved
Itraconazole	Itraconazole may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Ivabradine	Ivabradine may increase the QTc-prolonging activities of Procainamide.	Approved
Ketoconazole	Ketoconazole may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Lamotrigine	The serum concentration of Procainamide can be increased when it is combined with Lamotrigine.	Approved, Investigational
Lapatinib	Lapatinib may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Lenvatinib	Lenvatinib may increase the QTc-prolonging activities of Procainamide.	Approved
Leuprolide	Leuprolide may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Levofloxacin	Levofloxacin may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Lithium	Lithium may increase the QTc-prolonging activities of Procainamide.	Approved
Lopinavir	Procainamide may increase the QTc-prolonging activities of Lopinavir.	Approved
Lorcaserin	The metabolism of Procainamide can be decreased when combined with Lorcaserin.	Approved
Lumefantrine	Procainamide may increase the QTc-prolonging activities of Lumefantrine.	Approved
Lurasidone	Lurasidone may increase the QTc-prolonging activities of Procainamide.	Approved
Maprotiline	Maprotiline may increase the QTc-prolonging activities of Procainamide.	Approved
Mefloquine	Mefloquine may increase the QTc-prolonging activities of Procainamide.	Approved
Methadone	Methadone may increase the QTc-prolonging activities of Procainamide.	Approved
Methotrimeprazine	Methotrimeprazine may increase the QTc-prolonging activities of Procainamide.	Approved
Metoclopramide	Metoclopramide may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Metocurine	Procainamide may increase the neuromuscular blocking activities of Metocurine.	Approved
Metocurine Iodide	Procainamide may increase the neuromuscular blocking activities of Metocurine Iodide.	Withdrawn
Metoprolol	The metabolism of Procainamide can be decreased when combined with Metoprolol.	Approved, Investigational
Metronidazole	Metronidazole may increase the QTc-prolonging activities of Procainamide.	Approved
Mifepristone	Mifepristone may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Mirabegron	Mirabegron may increase the QTc-prolonging activities of Procainamide.	Approved
Mirtazapine	Mirtazapine may increase the QTc-prolonging activities of Procainamide.	Approved
Mivacurium	Procainamide may increase the neuromuscular blocking activities of Mivacurium.	Approved
Moexipril	Moexipril may increase the QTc-prolonging activities of Procainamide.	Approved
Moxifloxacin	Moxifloxacin may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Nelfinavir	Nelfinavir may increase the QTc-prolonging activities of Procainamide.	Approved
Neosaxitoxin	Procainamide may increase the neuromuscular blocking activities of Neosaxitoxin.	Investigational
Nevirapine	The metabolism of Procainamide can be decreased when combined with Nevirapine.	Approved
Nicardipine	Nicardipine may increase the QTc-prolonging activities of Procainamide.	Approved
Nilotinib	Procainamide may increase the QTc-prolonging activities of Nilotinib.	Approved, Investigational
Norfloxacin	Norfloxacin may increase the QTc-prolonging activities of Procainamide.	Approved
Nortriptyline	Nortriptyline may increase the QTc-prolonging activities of Procainamide.	Approved
Octreotide	Octreotide may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Ofloxacin	Ofloxacin may increase the QTc-prolonging activities of Procainamide.	Approved
Olanzapine	Olanzapine may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Olodaterol	Olodaterol may increase the QTc-prolonging activities of Procainamide.	Approved
Ondansetron	Ondansetron may increase the QTc-prolonging activities of Procainamide.	Approved
Oxytocin	Oxytocin may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Paliperidone	Procainamide may increase the QTc-prolonging activities of Paliperidone.	Approved
Pancuronium	Procainamide may increase the neuromuscular blocking activities of Pancuronium.	Approved
Panobinostat	The serum concentration of Procainamide can be increased when it is combined with Panobinostat.	Approved, Investigational
Paroxetine	Paroxetine may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Pasireotide	Pasireotide may increase the QTc-prolonging activities of Procainamide.	Approved
Pazopanib	Pazopanib may increase the QTc-prolonging activities of Procainamide.	Approved
Peginterferon alfa-2b	The serum concentration of Procainamide can be decreased when it is combined with Peginterferon alfa-2b.	Approved
Pentamidine	Pentamidine may increase the QTc-prolonging activities of Procainamide.	Approved
Perflutren	Perflutren may increase the QTc-prolonging activities of Procainamide.	Approved
Pimozide	Procainamide may increase the QTc-prolonging activities of Pimozide.	Approved
Pipecuronium	Procainamide may increase the neuromuscular blocking activities of Pipecuronium.	Approved
Posaconazole	Posaconazole may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational, Vet Approved
Primaquine	Primaquine may increase the QTc-prolonging activities of Procainamide.	Approved
Promazine	Promazine may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Promethazine	Promethazine may increase the QTc-prolonging activities of Procainamide.	Approved
Propafenone	Propafenone may increase the arrhythmogenic activities of Procainamide.	Approved
Propofol	Propofol may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational, Vet Approved
Protriptyline	Protriptyline may increase the QTc-prolonging activities of Procainamide.	Approved
Quetiapine	Procainamide may increase the QTc-prolonging activities of Quetiapine.	Approved
Quinidine	Quinidine may increase the QTc-prolonging activities of Procainamide.	Approved
Quinine	Quinine may increase the QTc-prolonging activities of Procainamide.	Approved
Ranitidine	The serum concentration of Procainamide can be increased when it is combined with Ranitidine.	Approved
Ranolazine	Ranolazine may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Rapacuronium	Procainamide may increase the neuromuscular blocking activities of Rapacuronium.	Withdrawn
Rilpivirine	Rilpivirine may increase the QTc-prolonging activities of Procainamide.	Approved
Risperidone	Risperidone may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Ritonavir	Ritonavir may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Rocuronium	Procainamide may increase the neuromuscular blocking activities of Rocuronium.	Approved
Rolapitant	The metabolism of Procainamide can be decreased when combined with Rolapitant.	Approved
Ropinirole	The metabolism of Procainamide can be decreased when combined with Ropinirole.	Approved, Investigational
Salbutamol	Salbutamol may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Salmeterol	Salmeterol may increase the QTc-prolonging activities of Procainamide.	Approved
Saquinavir	Saquinavir may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Sertraline	Sertraline may increase the QTc-prolonging activities of Procainamide.	Approved
Sevoflurane	Sevoflurane may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Solifenacin	Solifenacin may increase the QTc-prolonging activities of Procainamide.	Approved
Sorafenib	Sorafenib may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Sotalol	Sotalol may increase the QTc-prolonging activities of Procainamide.	Approved
Stiripentol	The metabolism of Procainamide can be decreased when combined with Stiripentol.	Approved
Succinylcholine	Procainamide may increase the neuromuscular blocking activities of Succinylcholine.	Approved
Sulfamethoxazole	Sulfamethoxazole may increase the QTc-prolonging activities of Procainamide.	Approved
Sulfisoxazole	Sulfisoxazole may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Sulpiride	The risk or severity of adverse effects can be increased when Procainamide is combined with Sulpiride.	Approved
Sunitinib	Sunitinib may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Tamoxifen	Tamoxifen may increase the QTc-prolonging activities of Procainamide.	Approved
Telavancin	Telavancin may increase the QTc-prolonging activities of Procainamide.	Approved
Telithromycin	Telithromycin may increase the QTc-prolonging activities of Procainamide.	Approved
Terbinafine	The metabolism of Procainamide can be decreased when combined with Terbinafine.	Approved, Investigational, Vet Approved
Terbutaline	Terbutaline may increase the QTc-prolonging activities of Procainamide.	Approved
Tetrabenazine	Procainamide may increase the QTc-prolonging activities of Tetrabenazine.	Approved
Thioridazine	Thioridazine may increase the QTc-prolonging activities of Procainamide.	Withdrawn
Thiothixene	Thiothixene may increase the QTc-prolonging activities of Procainamide.	Approved
Ticlopidine	The metabolism of Procainamide can be decreased when combined with Ticlopidine.	Approved
Tipranavir	The metabolism of Procainamide can be decreased when combined with Tipranavir.	Approved, Investigational
Tizanidine	Tizanidine may increase the QTc-prolonging activities of Procainamide.	Approved
Tolterodine	Tolterodine may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Toremifene	Toremifene may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Tranylcypromine	The metabolism of Procainamide can be decreased when combined with Tranylcypromine.	Approved
Trazodone	Trazodone may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Treprostinil	Treprostinil may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Trimethoprim	The serum concentration of the active metabolites of Procainamide can be increased when Procainamide is used in combination with Trimethoprim.	Approved, Vet Approved
Trimipramine	Trimipramine may increase the QTc-prolonging activities of Procainamide.	Approved
Triptorelin	Triptorelin may increase the QTc-prolonging activities of Procainamide.	Approved, Vet Approved
Tubocurarine	Procainamide may increase the neuromuscular blocking activities of Tubocurarine.	Approved
Vandetanib	Procainamide may increase the QTc-prolonging activities of Vandetanib.	Approved
Vardenafil	Vardenafil may increase the QTc-prolonging activities of Procainamide.	Approved
Vecuronium	Procainamide may increase the neuromuscular blocking activities of Vecuronium.	Approved
Vemurafenib	Procainamide may increase the QTc-prolonging activities of Vemurafenib.	Approved
Venlafaxine	Venlafaxine may increase the QTc-prolonging activities of Procainamide.	Approved
Vilanterol	Vilanterol may increase the QTc-prolonging activities of Procainamide.	Approved
Voriconazole	Voriconazole may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Vorinostat	Vorinostat may increase the QTc-prolonging activities of Procainamide.	Approved, Investigational
Ziprasidone	Ziprasidone may increase the QTc-prolonging activities of Procainamide.	Approved
Zuclopenthixol	Procainamide 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 References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15169
KEGG Compound	C07401
PubChem Compound	4913
PubChem Substance	46507313
ChemSpider	4744
BindingDB	39344
ChEBI	8428
ChEMBL	CHEMBL640
Therapeutic Targets Database	DAP000516
PharmGKB	PA451108
Drug Product Database	9702
RxList	http://www.rxlist.com/cgi/generic3/procain.htm
Drugs.com	http://www.drugs.com/cdi/procainamide.html
Wikipedia	Procainamide

ATC Codes

C01BA02 — Procainamide

AHFS Codes

24:04.04.04

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (72 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Prevention	Arrythmias / Cardiovascular Disease (CVD) / Heart Arrest / Heart Diseases / Myocardial Infarction (MI) / Severe ventricular arrhythmias	1
3	Completed	Treatment	Arrythmias / Cardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Diseases / Severe ventricular arrhythmias / Ventricular Arrythmias / Ventricular Tachycardia (VT)	1
3	Completed	Treatment	Arrythmias / Cardiovascular Disease (CVD) / Heart Diseases / Nonvalvular Atrial Fibrillation	1
3	Completed	Treatment	Nonvalvular Atrial Fibrillation	1
3	Terminated	Treatment	Heart Failure, Unspecified / Nonvalvular Atrial Fibrillation	1
4	Completed	Treatment	Brugada Syndrome / Nonvalvular Atrial Fibrillation / Ventricular Tachycardia (VT)	1
Not Available	Not Yet Recruiting	Treatment	Arrythmias	1
Not Available	Unknown Status	Diagnostic	Nonvalvular Atrial Fibrillation	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

E.R. Squibb and Sons LLC
Hospira Inc.
Ivax Pharmaceuticals
Kaiser Foundation Hospital
Major Pharmaceuticals
Mckesson Corp.
Monarch Pharmacy
Murfreesboro Pharmaceutical Nursing Supply
Neuman Distributors Inc.
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
United Research Laboratories Inc.

Dosage forms

Form	Route	Strength
Capsule	Oral	250 mg
Capsule	Oral	375 g
Capsule	Oral	500 mg
Injection	Intramuscular; Intravenous	100 mg/mL
Injection, solution	Intramuscular; Intravenous	100 mg/mL
Injection, solution	Intramuscular; Intravenous	500 mg/mL
Solution	Intramuscular; Intravenous	100 mg
Tablet, extended release	Oral	250 mg
Tablet, extended release	Oral	500 mg
Tablet, extended release	Oral	750 mg
Capsule	Oral	375 mg
Liquid	Intramuscular; Intravenous	100 mg

Prices

Unit description	Cost	Unit
Procainamide 500 mg/ml vial	6.45USD	ml
Procainamide 100 mg/ml vial	1.29USD	ml
Procan Sr 750 mg Sustained-Release Tablet	0.91USD	tablet
Procan Sr 500 mg Sustained-Release Tablet	0.56USD	tablet
Procan Sr 250 mg Sustained-Release Tablet	0.4USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5656296	No	1994-08-12	2014-08-12	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	165-169 °C	Not Available
water solubility	5050 mg/L	Not Available
logP	0.88	HANSCH,C ET AL. (1995)
pKa	9.32	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	3.02 mg/mL	ALOGPS
logP	1.42	ALOGPS
logP	0.95	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.75	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.25 m³·mol^-1	ChemAxon
Polarizability	27.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9561
Blood Brain Barrier	+	0.9675
Caco-2 permeable	+	0.666
P-glycoprotein substrate	Substrate	0.7739
P-glycoprotein inhibitor I	Non-inhibitor	0.9452
P-glycoprotein inhibitor II	Non-inhibitor	0.9654
Renal organic cation transporter	Non-inhibitor	0.7526
CYP450 2C9 substrate	Non-substrate	0.8624
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Non-substrate	0.6306
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9384
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9606
CYP450 3A4 inhibitor	Non-inhibitor	0.9238
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8833
Ames test	Non AMES toxic	0.7822
Carcinogenicity	Non-carcinogens	0.5352
Biodegradation	Not ready biodegradable	0.9855
Rat acute toxicity	2.1133 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9454
hERG inhibition (predictor II)	Non-inhibitor	0.648

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03dr-1940000000-b9d8d6702d2ec39984a3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Aminobenzamides

Alternative Parents

Benzamides / Benzoyl derivatives / Aniline and substituted anilines / Primary aromatic amines / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic oxides

Substituents

Aminobenzamide / Benzamide / Benzoyl / Aniline or substituted anilines / Primary aromatic amine / Carboxamide group / Amino acid or derivatives / Tertiary aliphatic amine / Tertiary amine / Secondary carboxylic acid amide

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzamides (CHEBI:8428 )

Targets

Details

1. Sodium channel protein type 5 subunit alpha

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
Uniprot Name:: Sodium channel protein type 5 subunit alpha
Molecular Weight:: 226937.475 Da

References

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 ]
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 ]
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 ]
Brugada J, Brugada R, Brugada P: [Brugada syndrome]. Arch Mal Coeur Vaiss. 1999 Jul;92(7):847-50. [PubMed:10443304 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Details

2. DNA (cytosine-5)-methyltransferase 1

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
Uniprot Name:: DNA (cytosine-5)-methyltransferase 1
Molecular Weight:: 183163.635 Da

References

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 ]
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 ]
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 ]
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 ]

Details

3. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Human
Pharmacological action: unknown
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
Uniprot Name:: Potassium voltage-gated channel subfamily H member 2
Molecular Weight:: 126653.52 Da

References

Chiu PJ, Marcoe KF, Bounds SE, Lin CH, Feng JJ, Lin A, Cheng FC, Crumb WJ, Mitchell R: Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels. J Pharmacol Sci. 2004 Jul;95(3):311-9. [PubMed:15272206 ]

Enzymes

Details

1. Cytochrome P450 2D6

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
Uniprot Name:: Cytochrome P450 2D6
Molecular Weight:: 55768.94 Da

References

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 ]
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 ]

Details

2. Cholinesterase

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
Uniprot Name:: Cholinesterase
Molecular Weight:: 68417.575 Da

References

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 ]
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

Details

1. Solute carrier family 22 member 2

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
Uniprot Name:: Solute carrier family 22 member 2
Molecular Weight:: 62579.99 Da

References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Details

2. Solute carrier family 22 member 1

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
Uniprot Name:: Solute carrier family 22 member 1
Molecular Weight:: 61153.345 Da

References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Details

3. Solute carrier family 22 member 3

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
Uniprot Name:: Solute carrier family 22 member 3
Molecular Weight:: 61279.485 Da

References

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 ]

Details

4. Solute carrier family 22 member 5

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
Uniprot Name:: Solute carrier family 22 member 5
Molecular Weight:: 62751.08 Da

References

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 ]
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 ]
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 ]
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 ]

Details

5. Solute carrier family 22 member 4

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
Uniprot Name:: Solute carrier family 22 member 4
Molecular Weight:: 62154.48 Da

References

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 ]
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 ]

Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:55

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Structure for DB01035 (Procainamide)

Targets

References

References

References

Enzymes

References

References

Transporters

References

References

References

References

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