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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Procainamide
- Accession Number
- DB01035 (APRD00509)
- Type
- Small Molecule
- Groups
- Approved
- Description
A derivative of procaine with less CNS action. [PubChem]
- Structure
Structure for Procainamide (DB01035)
- 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 Procainamide Hydrochloride SI4064O0LX 614-39-1 ABTXGJFUQRCPNH-UHFFFAOYSA-N - 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 250 mg Oral Erfa Canada 2012 Inc 1985-12-31 Not applicable 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 500 mg Oral Erfa Canada 2012 Inc 1985-12-31 2015-06-05 Canada Procanbid Tablet, film coated, extended release 500 mg/1 Oral Monarch Pharmaceuticals, Inc. 1996-01-31 2008-11-11 US 
Procanbid Tablet, film coated, extended release 1000 mg/1 Oral Monarch Pharmaceuticals, Inc. 1996-01-31 2008-11-11 US Pronestyl Tablet, film coated 375 mg/1 Oral E.R. Squibb & Sons, L.L.C. 2006-01-01 2007-05-31 US - 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 100 mg/1mL Intramuscular; Intravenous Hospira, Inc. 2006-03-08 Not applicable US Procainamide Hydrochloride Capsule 250 mg/1 Oral Physicians Total Care, Inc. 1976-12-02 2004-12-31 US Procainamide Hydrochloride Injection 1000 mg/1 Intramuscular; Intravenous Medical Purchasing Solutions, Llc 2017-10-18 Not applicable US Procainamide Hydrochloride Injection 1000 mg/1 Intramuscular; Intravenous Nexus Pharmaceuticals Inc 2017-10-18 Not applicable US Procainamide Hydrochloride Injection, solution 100 mg/1mL Intramuscular; Intravenous Physicians Total Care, Inc. 1986-02-12 2011-06-30 US Procainamide Hydrochloride Capsule 250 mg/1 Oral IVAX Pharmaceuticals, Inc. 1980-01-07 2009-09-30 US Procainamide Hydrochloride Injection, solution 500 mg/1mL Intramuscular; Intravenous Cardinal Health 1986-02-12 2016-12-31 US - International/Other Brands
- Biocoryl / Procan / Procanbid / Procapan / Pronestyl
- Categories
- Acids, Carbocyclic
- Agents that produce neuromuscular block
- Amides
- Aminobenzoates
- Antiarrhythmic agents
- Antiarrhythmics, Class I
- Antiarrhythmics, Class Ia
- Benzamides and benzamide derivatives
- Benzene Derivatives
- Benzoates
- Cardiac Therapy
- Cardiovascular Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Substrates
- Highest Risk QTc-Prolonging Agents
- MATE 1 Substrates
- MATE 2 Substrates
- MATE substrates
- Membrane Transport Modulators
- Narrow Therapeutic Index Drugs
- Neuromuscular Agents
- OCT2 Inhibitors
- para-Aminobenzoates
- QTc Prolonging Agents
- Sodium Channel Blockers
- Voltage-Gated Sodium Channel Blockers
- 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 inhibitorHuman UDNA (cytosine-5)-methyltransferase 1 otherHuman UPotassium voltage-gated channel subfamily H member 2 inhibitorHuman - Absorption
75 to 95%
- Volume of distribution
- 2 L/kg
- Protein binding
15 to 20%
- Metabolism
Hepatic
- 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 Abiraterone The serum concentration of Procainamide can be increased when it is combined with Abiraterone. Acetaminophen Acetaminophen may decrease the excretion rate of Procainamide which could result in a higher serum level. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Procainamide. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Procainamide which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Procainamide which could result in a higher serum level. Adefovir Dipivoxil Adefovir Dipivoxil may decrease the excretion rate of Procainamide which could result in a higher serum level. Agmatine The serum concentration of Agmatine can be increased when it is combined with Procainamide. Alcuronium Procainamide may increase the neuromuscular blocking activities of Alcuronium. Alendronic acid The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Alendronic acid is combined with Procainamide. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Procainamide. - 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 / 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 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 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
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 oxides 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
- 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 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]
- 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 ...
- 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]
- 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 ...
- 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
- 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...
- 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]
- 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
- 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, 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]
- 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-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]
- 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]
- 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 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]
- 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...
- 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]
- Kind
- Protein
- Organism
- Human
- 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]
- Kind
- Protein
- Organism
- Human
- 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 October 16, 2018 08:33