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
Procainamide-250 Cap 250mg	Capsule	250 mg	Oral	Pro Doc Limitee	1987-12-31	2000-07-31
Procainamide-375 Cap 375mg	Capsule	375 mg	Oral	Pro Doc Limitee	1987-12-31	2000-07-31
Procainamide-500 Cap 500mg	Capsule	500 mg	Oral	Pro Doc Limitee	1987-12-31	2000-07-31
Procan SR	Tablet, extended release	500 mg	Oral	Erfa Canada 2012 Inc	1985-12-31	2015-06-05
Procan SR	Tablet, extended release	750 mg	Oral	Erfa Canada 2012 Inc	1985-12-31	2015-06-05
Procan SR	Tablet, extended release	250 mg	Oral	Erfa Canada 2012 Inc	1985-12-31	Not applicable
Procanbid	Tablet, film coated, extended release	500 mg/1	Oral	Monarch Pharmaceuticals, Inc.	1996-01-31	2008-11-11
Procanbid	Tablet, film coated, extended release	1000 mg/1	Oral	Monarch Pharmaceuticals, Inc.	1996-01-31	2008-11-11
Pronestyl	Capsule, gelatin coated	500 mg/1	Oral	E.R. Squibb & Sons, L.L.C.	1994-01-01	2007-04-01

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
Apo-procainamide Cap 375mg	Capsule	375 g	Oral	Apotex Corporation	1986-12-31	Not applicable
Apo-procainamide Cap 500mg	Capsule	500 mg	Oral	Apotex Corporation	1986-12-31	Not applicable
Procainamide Hydrochloride	Injection, solution	100 mg/1mL	Intramuscular; Intravenous	Physicians Total Care, Inc.	1986-02-12	2011-06-30
Procainamide Hydrochloride	Injection, solution	500 mg/1mL	Intramuscular; Intravenous	Cardinal Health	1986-02-12	2016-12-31
Procainamide Hydrochloride	Capsule	375 mg/1	Oral	IVAX Pharmaceuticals, Inc.	1980-01-07	2004-02-27
Procainamide Hydrochloride	Injection	1000 mg/1	Intramuscular; Intravenous	Medical Purchasing Solutions, Llc	2017-10-18	Not applicable
Procainamide Hydrochloride	Capsule	500 mg/1	Oral	Physicians Total Care, Inc.	1977-06-14	2004-12-31
Procainamide Hydrochloride	Injection	100 mg/1mL	Intramuscular; Intravenous	International Medication Systems, Limited	2016-12-21	Not applicable
Procainamide Hydrochloride	Injection, solution	500 mg/1mL	Intramuscular; Intravenous	Hospira, Inc.	2005-08-29	Not applicable

International/Other Brands

Biocoryl / Procan / Procanbid / Procapan / Pronestyl

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.

Associated Conditions

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	Actions	Organism
USodium channel protein type 5 subunit alpha	inhibitor	Humans
UDNA (cytosine-5)-methyltransferase 1	other	Humans
UPotassium voltage-gated channel subfamily H member 2	inhibitor	Humans

Absorption

75 to 95%

Volume of distribution

2 L/kg

Protein binding

15 to 20%

Metabolism

Hepatic

Procainamide
N-Acetyl-3-hydroxyprocainamide

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
Procainamide (Antiarrhythmic) Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
4-Methoxyamphetamine	The metabolism of Procainamide can be decreased when combined with 4-Methoxyamphetamine.
Abacavir	Abacavir may decrease the excretion rate of Procainamide which could result in a higher serum level.
Abatacept	The metabolism of Procainamide can be increased when combined with Abatacept.
Abemaciclib	The excretion of Procainamide can be decreased when combined with Abemaciclib.
Abexinostat	The risk or severity of QTc prolongation can be increased when Abexinostat is combined with Procainamide.
Abiraterone	The metabolism of Procainamide can be decreased when combined with Abiraterone.
Acarbose	Acarbose may decrease the excretion rate of Procainamide which could result in a higher serum level.
Acebutolol	The metabolism of Procainamide can be decreased when combined with Acebutolol.
Aceclofenac	Aceclofenac may decrease the excretion rate of Procainamide which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Procainamide which could result in a higher serum level.

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

Human Metabolome Database: HMDB0015169
KEGG Compound: C07401
PubChem Compound: 4913
PubChem Substance: 46507313
ChemSpider: 4744
BindingDB: 39344
ChEBI: 8428
ChEMBL: CHEMBL640
Therapeutic Targets Database: DAP000516
PharmGKB: PA451108
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Procainamide

ATC Codes

C01BA02 — Procainamide

AHFS Codes

24:04.04.04 — Class IA Antiarrythmics

MSDS

Download (72 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Prevention	Arrythmias / Cardiovascular Disease (CVD) / Heart Arrest / Heart Diseases / Myocardial Infarction / Ventricular Fibrillation	1
3	Completed	Treatment	Arrhythmia of ventricular origin / Arrythmias / Cardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Diseases / Ventricular Fibrillation / 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	Completed	Diagnostic	Nonvalvular Atrial Fibrillation	1
Not Available	Withdrawn	Treatment	Arrythmias	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	375 g
Capsule	Oral	250 mg/1
Capsule	Oral	375 mg/1
Capsule	Oral	500 mg/1
Injection	Intramuscular; Intravenous	100 mg/1mL
Injection	Intramuscular; Intravenous	1000 mg/1
Injection, solution	Intramuscular; Intravenous	100 mg/1mL
Injection, solution	Intramuscular; Intravenous	500 mg/1mL
Solution	Intramuscular; Intravenous	100 mg
Capsule	Oral	250 mg
Tablet, extended release	Oral	250 mg
Tablet, extended release	Oral	500 mg
Tablet, extended release	Oral	750 mg
Tablet, film coated, extended release	Oral	1000 mg/1
Tablet, film coated, extended release	Oral	500 mg/1
Capsule, gelatin coated	Oral	250 mg/1
Capsule, gelatin coated	Oral	375 mg/1
Capsule, gelatin coated	Oral	500 mg/1
Tablet, film coated	Oral	250 mg/1
Tablet, film coated	Oral	375 mg/1
Tablet, film coated	Oral	500 mg/1
Capsule	Oral	375 mg
Capsule	Oral	500 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	1997-08-12	2014-08-12

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	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03dr-1940000000-b9d8d6702d2ec39984a3

Taxonomy

Description: This compound belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Benzene and substituted derivatives
Sub Class: Benzoic acids and derivatives
Direct Parent: Aminobenzamides
Alternative Parents: Benzamides / Benzoyl derivatives / Aniline and substituted anilines / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxidesHydrocarbon derivatives
show 1 more
Substituents: Aminobenzamide / Benzamide / Benzoyl / Aniline or substituted anilines / Amino acid or derivatives / Carboxamide group / Tertiary aliphatic amine / Tertiary amine / Secondary carboxylic acid amide / Carboxylic acid derivative
show 10 more
Molecular Framework: Aromatic homomonocyclic compounds
External Descriptors: benzamides (CHEBI:8428)

Targets

Details1. Sodium channel protein type 5 subunit alpha

Kind: Protein
Organism: Humans
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 pr...
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]

Details2. DNA (cytosine-5)-methyltransferase 1

Kind: Protein
Organism: Humans
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 ...
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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	138038.43	N/A	N/A	15911273 / 21185626

Details3. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Humans
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 ...
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

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
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...
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]

Details2. Cholinesterase

Kind: Protein
Organism: Humans
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

Details1. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
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, creat...
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]

Details2. Solute carrier family 22 member 1

Kind: Protein
Organism: Humans
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-methylnico...
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]

Details3. Solute carrier family 22 member 3

Kind: Protein
Organism: Humans
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]

Details4. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
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 cat...
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]

Details5. Solute carrier family 22 member 4

Kind: Protein
Organism: Humans
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...
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]

Details6. Multidrug and toxin extrusion protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Monovalent cation:proton antiporter activity
Specific Function: Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name: SLC47A1
Uniprot ID: Q96FL8
Uniprot Name: Multidrug and toxin extrusion protein 1
Molecular Weight: 61921.585 Da

References

Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]
Motohashi H, Inui K: Organic cation transporter OCTs (SLC22) and MATEs (SLC47) in the human kidney. AAPS J. 2013 Apr;15(2):581-8. doi: 10.1208/s12248-013-9465-7. Epub 2013 Feb 22. [PubMed:23435786]
Somogyi A, Muirhead M: Pharmacokinetic interactions of cimetidine 1987. Clin Pharmacokinet. 1987 May;12(5):321-66. doi: 10.2165/00003088-198712050-00002. [PubMed:3301148]
Ito S, Kusuhara H, Yokochi M, Toyoshima J, Inoue K, Yuasa H, Sugiyama Y: Competitive inhibition of the luminal efflux by multidrug and toxin extrusions, but not basolateral uptake by organic cation transporter 2, is the likely mechanism underlying the pharmacokinetic drug-drug interactions caused by cimetidine in the kidney. J Pharmacol Exp Ther. 2012 Feb;340(2):393-403. doi: 10.1124/jpet.111.184986. Epub 2011 Nov 9. [PubMed:22072731]

Details7. Multidrug and toxin extrusion protein 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Drug transmembrane transporter activity
Specific Function: Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name: SLC47A2
Uniprot ID: Q86VL8
Uniprot Name: Multidrug and toxin extrusion protein 2
Molecular Weight: 65083.915 Da

References

Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [PubMed:17509534]
Motohashi H, Inui K: Organic cation transporter OCTs (SLC22) and MATEs (SLC47) in the human kidney. AAPS J. 2013 Apr;15(2):581-8. doi: 10.1208/s12248-013-9465-7. Epub 2013 Feb 22. [PubMed:23435786]
Somogyi A, Muirhead M: Pharmacokinetic interactions of cimetidine 1987. Clin Pharmacokinet. 1987 May;12(5):321-66. doi: 10.2165/00003088-198712050-00002. [PubMed:3301148]
Ito S, Kusuhara H, Yokochi M, Toyoshima J, Inoue K, Yuasa H, Sugiyama Y: Competitive inhibition of the luminal efflux by multidrug and toxin extrusions, but not basolateral uptake by organic cation transporter 2, is the likely mechanism underlying the pharmacokinetic drug-drug interactions caused by cimetidine in the kidney. J Pharmacol Exp Ther. 2012 Feb;340(2):393-403. doi: 10.1124/jpet.111.184986. Epub 2011 Nov 9. [PubMed:22072731]

Drug created on June 13, 2005 07:24 / Updated on January 22, 2019 17:56

Procainamide

Identification

Structure for Procainamide (DB01035)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Enzymes

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Transporters

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