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QuickView for Procainamide (compound)

Summary
General Info

PubChem

PubChem Compound 4913

Name:	Procainamide
PubChem Compound ID:	4913
Description:	A derivative of PROCAINE with less CNS action. It also acts as a non-nucleoside inhibitor of DNA METHYLATION and has led to SYSTEMIC LUPUS ERYTHEMATOSUS.
Molecular formula:	C₁₃H₂₁N₃O
Molecular weight:	235.325 g/mol
Synonyms:	Novocaine amide; Bio2_000663; KBio3_001729; Spectrum3_000555; Procainamida [INN-Spanish]; Spectrum4_000487; Spectrum2_001295; Lopac-P-9391; Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-; NSC 27461. show more » Novocaine amide; Bio2_000663; KBio3_001729; Spectrum3_000555; Procainamida [INN-Spanish]; Spectrum4_000487; Spectrum2_001295; Lopac-P-9391; Benzamide, 4-amino-N-(2-(diethylamino)ethyl)-; NSC 27461; KBio2_006452; 51-06-9; p-Amino-N-(2-diethylaminoethyl)benzamide; Bio2_000183; DivK1c_000931; 614-39-1; Benzamide, 4-amino-N-[2- (diethylamino)ethyl]-; Novocainamid; EINECS 200-078-8; Procaine amide; CBDivE_003757; Novocamid; Biocoryl; Prestwick0_000337; Procamide; NINDS_000931; p-Aminobenzoic diethylaminoethylamide; NSC27461; KBioSS_000183; Procainamide; KBio1_000931; Benzamide, 4-amino-N-(2-(diethylamino)ethyl)- (9CI); HSDB 3170; Pronestyl; Procainamidum [INN-Latin]; Benzamide, p-amino-N-[2- (diethylamino)ethyl]-; CAS-614-39-1; KBio2_002751; KBio2_003884; Benzamide, p-amino-N-(2-(diethylamino)ethyl)-; Bio1_000880; 4-Amino-N-(2-(diethylamino)ethyl)benzamide; Spectrum_000836; BRN 2214285; Procapan (free base); Maybridge1_004389; KBioGR_000973; Benzamide, p-amino-N-[2-(diethylamino)ethyl]-; Benzamide, 4-amino-N-[2-(diethylamino)ethyl]-; SPBio_002294; KBio2_001316; Novocainamide; 2-Diethylaminoethylamid kyseliny p-aminobenzoove [Czech]; KBio2_005319; KBio3_000366; KBioGR_000183; KBioSS_001316; Bio1_001369; KBio3_000365; Prestwick1_000337; NCGC00015859-02; C07401; SPBio_001329; NCGC00015859-01; 4-14-00-01154 (Beilstein Handbook Reference); KBio2_000183; Bio1_000391 show less «

DrugBank

Identification

Name:	Procainamide
Name (isomeric):	DB01035
Drug Type:	small molecule
Description:	A derivative of PROCAINE with less CNS action. It also acts as a non-nucleoside inhibitor of DNA METHYLATION and has led to SYSTEMIC LUPUS ERYTHEMATOSUS.
Brand:	Procamide, Procaine Amide, Procan Sr, Procainamide Hcl, Procanbid, Promine, Procapan, Biocoryl, Procan, Pronestyl, Novocainamid, Novocaine Amide, Novocamid, Novocainamide, Pronestyl-Sr
Category:	Antiarrhythmic Agents, Anti-Arrhythmia Agents
CAS number:	51-06-9

Pharmacology

Indication:	For the treatment of life-threatening ventricular arrhythmias.
Pharmacology:	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 ef... show more » 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. show less «
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.
Absorption:	75 to 95%
Protein binding:	15 to 20%
Biotransformation:	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
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

Interactions

Food interaction:

Avoid alcohol.

Take with food to reduce irritation.

Drug interaction:

Ranitidine	The histamine H2-receptor antagonist, ranitidine, may increase the effect of procainamide.
Terbinafine	Terbinafine may reduce the metabolism and clearance of Procainamide. Consider alternate therapy or monitor for therapeutic/adverse effects of Procainamide if Terbinafine is initiated, discontinued or dose changed.
Quinidine barbiturate	Quinidine increases the effect of procainamide
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Donepezil	Possible antagonism of action

Ranitidine	The histamine H2-receptor antagonist, ranitidine, may increase the effect of procainamide.
Terbinafine	Terbinafine may reduce the metabolism and clearance of Procainamide. Consider alternate therapy or monitor for therapeutic/adverse effects of Procainamide if Terbinafine is initiated, discontinued or dose changed.
Quinidine barbiturate	Quinidine increases the effect of procainamide
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Donepezil	Possible antagonism of action
Trimethoprim	Trimethoprim may reduce the clearance of Procainamide. Alternative treatments should be considered. If Trimethoprim is initiated or the dose is increased, monitor for increased toxicity of Procainamide (e.g. QTc intervals, EKG, serum drug concentrations). If Trimethoprim is discontinued or the dose decreased, monitor for reduced effects of Procainamide.
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Ranolazine	Possible additive effect on QT prolongation
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.
Quinidine	Quinidine increases the effect of procainamide
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Ofloxacin	Ofloxacin may increase the effect of procainamide.
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Galantamine	Possible antagonism of action
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Dihydroquinidine barbiturate	Quinidine increases the effect of procainamide
Amiodarone	Amiodarone may increase serum levels and toxicity of procainamide.
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Levofloxacin	Levofloxacin may increase the effect of procainamide.
Cimetidine	The histamine H2-receptor antagonist, cimetidine, may increase the effect of procainamide.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Ciprofloxacin	Ciprofloxacin may increase the effect of procainamide.
Rivastigmine	Possible antagonism of action
Cisapride	Increased risk of cardiotoxicity and arrhythmias
Vardenafil	Increased risk of cardiotoxicity and arrhythmias
Voriconazole	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

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Targets

Sodium channel protein type 5 subunit alpha

DNA (cytosine-5)-methyltransferase 1

Enzymes

Cytochrome P450 2D6

Cholinesterase

Transporters

Solute carrier family 22 member 2

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-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity

UniProt ID:

O15244

Gene:

SLC22A2

Actions:

inhibitor

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.
View Article

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.
View Article

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.
View Article

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.
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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.
View Article

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.
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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.
View Article

Solute carrier family 22 member 1

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, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase

UniProt ID:

O15245

Gene:

SLC22A1

Actions:

inhibitor

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.
View Article

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.
View Article

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.
View Article

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.
View Article

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.
View Article

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.
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Solute carrier family 22 member 3

Organic cation/carnitine transporter 2

Organic cation/carnitine transporter 1