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MedKoo Cat#: 318572 | Name: Procainamide Hydrochloride
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Procainamide hydrochloride is the hydrochloride salt preparation of Procainamide, a potent blocker of Na+ channels. Procainamide demonstrates antiarrhythmic effects correlated with blockade of the Na+ channels. Procainamide hydrochloride is an inhibitor of DNA methyltransferase.

Chemical Structure

Procainamide Hydrochloride
Procainamide Hydrochloride
CAS# 614-39-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 318572

Name: Procainamide Hydrochloride

CAS#: 614-39-1 (HCl)

Chemical Formula: C13H22ClN3O

Exact Mass:

Molecular Weight: 271.79

Elemental Analysis: C, 57.45; H, 8.16; Cl, 13.04; N, 15.46; O, 5.89

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 450.00 2 Weeks
25g USD 850.00 2 Weeks
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Related CAS #
51-06-9 (free base); 614-39-1 (HCl)
Synonym
Procainamide Hydrochloride; Procainamide Hcl; Pronestyl; Procanbid; Procapan; Procaine Amide; Procamide; Procan; Procan SR; Procanbid; Pronestyl;
IUPAC/Chemical Name
4-amino-N-[2-(diethylamino)ethyl]benzamide;hydrochloride
InChi Key
ABTXGJFUQRCPNH-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H21N3O.ClH/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);1H
SMILES Code
CCN(CC)CCNC(=O)C1=CC=C(C=C1)N.Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Procainamide hydrochloride is the hydrochloride salt preparation of Procainamide, a potent blocker of Na+ channels.
In vitro activity:
Procaine, a local anesthetic drug, and procainamide, a drug for the treatment of cardiac arrhythmias, have been reported as inhibitors of DNA methylation, causing demethylation and reactivation of methylation-silenced genes such as RARbeta and GSTP1. This study demonstrates promoter demethylation of WIF-1; restoration of WIF-1 expression, and underexpression of cytosolic beta-catenin protein and TCF reporter activity, after procaine and procainamide treatment in H460 and A549 cell lines. The results provide the first evidence that procaine and procainamide reactivate WIF-1 in these cancer cells and downregulate the Wnt canonical pathway. Reference: Oncol Rep. 2009 Dec;22(6):1479-84. https://pubmed.ncbi.nlm.nih.gov/19885602/
In vivo activity:
Treatment of endotoxemic animals with procainamide not only inhibited the increased levels of DNMT1 and 5-methylcytosine but also ameliorated neutrophil infiltration and superoxide production in the lung. In addition, the anti-inflammatory gene, IL27RA, was down-regulated in the LPS group and up-regulated in the LPS + Procainamide group. Procainamide also diminished IL27RA methylation in the lung of endotoxemic rat. Moreover, both DNMT inhibitors procainamide and hydralazine improved hypotension, hypoglycemia, and multiple organ dysfunction of LPS-treated rats. This study suggests that the beneficial effects of procainamide could be attributed to the suppression of DNA methylation, neutrophil infiltration, superoxide production, and NO formation. Reference: PLoS One. 2016 Sep 23;11(9):e0163690. https://pubmed.ncbi.nlm.nih.gov/27661616/
Solvent mg/mL mM
Solubility
DMF 20.0 73.59
DMSO 39.3 144.72
Ethanol 16.0 58.87
PBS (pH 7.2) 10.0 36.79
Water 52.0 191.32
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 271.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Gao Z, Xu Z, Hung MS, Lin YC, Wang T, Gong M, Zhi X, Jablons DM, You L. Procaine and procainamide inhibit the Wnt canonical pathway by promoter demethylation of WIF-1 in lung cancer cells. Oncol Rep. 2009 Dec;22(6):1479-84. doi: 10.3892/or_00000590. PMID: 19885602. 2. 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. doi: 10.1074/jbc.M505593200. Epub 2005 Oct 17. PMID: 16230360; PMCID: PMC1989680. 3. Shih CC, Liao MH, Hsiao TS, Hii HP, Shen CH, Chen SJ, Ka SM, Chang YL, Wu CC. Procainamide Inhibits DNA Methylation and Alleviates Multiple Organ Dysfunction in Rats with Endotoxic Shock. PLoS One. 2016 Sep 23;11(9):e0163690. doi: 10.1371/journal.pone.0163690. PMID: 27661616; PMCID: PMC5035080. 4. Pang JX, Sun LS, Wang XY, Yang SQ, Shan CW. Effect of procainamide on pulmonary thromboembolism and platelet malondialdehyde in mice. Zhongguo Yao Li Xue Bao. 1996 Nov;17(6):500-2. PMID: 9863141.
In vitro protocol:
1. Gao Z, Xu Z, Hung MS, Lin YC, Wang T, Gong M, Zhi X, Jablons DM, You L. Procaine and procainamide inhibit the Wnt canonical pathway by promoter demethylation of WIF-1 in lung cancer cells. Oncol Rep. 2009 Dec;22(6):1479-84. doi: 10.3892/or_00000590. PMID: 19885602. 2. 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. doi: 10.1074/jbc.M505593200. Epub 2005 Oct 17. PMID: 16230360; PMCID: PMC1989680.
In vivo protocol:
1. Shih CC, Liao MH, Hsiao TS, Hii HP, Shen CH, Chen SJ, Ka SM, Chang YL, Wu CC. Procainamide Inhibits DNA Methylation and Alleviates Multiple Organ Dysfunction in Rats with Endotoxic Shock. PLoS One. 2016 Sep 23;11(9):e0163690. doi: 10.1371/journal.pone.0163690. PMID: 27661616; PMCID: PMC5035080. 2. Pang JX, Sun LS, Wang XY, Yang SQ, Shan CW. Effect of procainamide on pulmonary thromboembolism and platelet malondialdehyde in mice. Zhongguo Yao Li Xue Bao. 1996 Nov;17(6):500-2. PMID: 9863141.
1: Viale M, Fenoglio C, de Totero D, Prigione I, Cassano A, Vincenti A, Bocca P, Gangemi R, Mariggiò MA. Potentiation of cisplatin-induced antiproliferative and apoptotic activities by the antiarrhythmic drug procainamide hydrochloride. Pharmacol Rep. 2016 Feb 28;68(3):654-661. doi: 10.1016/j.pharep.2016.02.002. [Epub ahead of print] PubMed PMID: 27026293. 2: Wang K, Guan X, Chai S, Zou Q, Zhang X, Zhang J. A novel, molecularly imprinted polymer sensor made using an oligomeric methyl silsesquioxane-TiO2 composite sol on a glassy carbon electrode for the detection of procainamide hydrochloride. Biosens Bioelectron. 2015 Feb 15;64:94-101. doi: 10.1016/j.bios.2014.08.053. Epub 2014 Aug 27. PubMed PMID: 25194802. 3: Karakus G, Akin Polat Z, Sahin Yaglıoglu A, Karahan M, Yenidunya AF. Synthesis, characterization, and assessment of cytotoxic, antiproliferative, and antiangiogenic effects of a novel procainamide hydrochloride-poly(maleic anhydride-co-styrene) conjugate. J Biomater Sci Polym Ed. 2013;24(10):1260-76. doi: 10.1080/09205063.2012.750209. Epub 2012 Dec 21. PubMed PMID: 23713427. 4: Wojnarowska Z, Roland CM, Swiety-Pospiech A, Grzybowska K, Paluch M. Anomalous electrical conductivity behavior at elevated pressure in the protic ionic liquid procainamide hydrochloride. Phys Rev Lett. 2012 Jan 6;108(1):015701. Epub 2012 Jan 5. PubMed PMID: 22304270. 5: Wojnarowska Z, Swiety-Pospiech A, Grzybowska K, Hawelek L, Paluch M, Ngai KL. Fundamentals of ionic conductivity relaxation gained from study of procaine hydrochloride and procainamide hydrochloride at ambient and elevated pressure. J Chem Phys. 2012 Apr 28;136(16):164507. doi: 10.1063/1.4705274. PubMed PMID: 22559496. 6: Ognio E, Chiavarina B, Peterka M, Mariggiò MA, Viale M. Study of feasibility of the treatment with procainamide hydrochloride and cisplatin in pregnant mice. Chem Biol Interact. 2006 Dec 15;164(3):232-40. Epub 2006 Oct 10. PubMed PMID: 17084828. 7: Sastry CS, Rao TT, Sailaja A. Spectrophotometric determination of nicoumalone, acebutolol hydrochloride and procainamide hydrochloride. Talanta. 1991 Sep;38(9):1057-60. PubMed PMID: 18965260. 8: Schaaf LJ, Robinson DH, Vogel GJ, Wulf BG, Drda KD, Moses JO. Stability of esmolol hydrochloride in the presence of aminophylline, bretylium tosylate, heparin sodium, and procainamide hydrochloride. Am J Hosp Pharm. 1990 Jul;47(7):1567-71. PubMed PMID: 2368749. 9: Kasmer RJ, Nara AR, Green JA, Chawla AK, Fleming GM. Comparable steady-state bioavailability between two preparations of conventional-release procainamide hydrochloride. Drug Intell Clin Pharm. 1987 Feb;21(2):183-6. PubMed PMID: 3829910. 10: Papich MG, Davis LE, Davis CA, McKiernan BC, Brown SA. Pharmacokinetics of procainamide hydrochloride in dogs. Am J Vet Res. 1986 Nov;47(11):2351-8. PubMed PMID: 2431636. 11: Baaske DM, Malick AW, Carter JE. Stability of procainamide hydrochloride in dextrose solutions. Am J Hosp Pharm. 1980 Aug;37(8):1050-2. PubMed PMID: 7405932. 12: Kadin H. Interference by traces of acetic anhydride in nonaqueous titrimetry of primary aromatic amines: improved titrations for procainamide hydrochloride. J Pharm Sci. 1974 Jun;63(6):919-23. PubMed PMID: 4852511. 13: Shapiro MS, Teitler A, Grob D. Procainamide hydrochloride sensitivity. Manifested by fever and chills. Minn Med. 1973 Dec;56(12):1041-4. PubMed PMID: 4271436. 14: Paine R. Procainamide hydrochloride and lupus erythematosus. JAMA. 1965 Oct 4;194(1):23-6. PubMed PMID: 4157597. 15: KAPLAN JM, WACHTEL HL, CZARNECKI SW, SAMPSON JJ. LUPUS-LIKE ILLNESS PRECIPITATED BY PROCAINAMIDE HYDROCHLORIDE. JAMA. 1965 May 10;192:444-7. PubMed PMID: 14284842. 16: Fenoglio C, Boncompagni E, Chiavarina B, Cafaggi S, Cilli M, Viale M. Morphological and histochemical evidence of the protective effect of procainamide hydrochloride on tissue damage induced by repeated administration of low doses of cisplatin. Anticancer Res. 2005 Nov-Dec;25(6B):4123-8. Erratum in: Anticancer Res. 2006 Jan-Feb;26(1a):445. PubMed PMID: 16309206. 17: Vannozzi MO, Ottone M, Mariggiò MA, Cafaggi S, Parodi B, Cilli M, Lindup E, Viale M. Pharmacokinetic and pharmacodynamic analysis of platinum after combined treatment of cisplatin and procainamide hydrochloride in mice bearing P388 leukemia. Anticancer Res. 2003 Mar-Apr;23(2B):1509-16. PubMed PMID: 12820417. 18: Zicca A, Cafaggi S, Mariggiò MA, Vannozzi MO, Ottone M, Bocchini V, Caviglioli G, Viale M. Reduction of cisplatin hepatotoxicity by procainamide hydrochloride in rats. Eur J Pharmacol. 2002 May 10;442(3):265-72. PubMed PMID: 12065080. 19: Allen LV Jr, Erickson MA 3rd. Stability of ketoconazole, metolazone, metronidazole, procainamide hydrochloride, and spironolactone in extemporaneously compounded oral liquids. Am J Health Syst Pharm. 1996 Sep 1;53(17):2073-8. PubMed PMID: 8870895. 20: Sianipar A, Parkin JE, Sunderland VB. Chemical incompatibility between procainamide hydrochloride and glucose following intravenous admixture. J Pharm Pharmacol. 1994 Dec;46(12):951-5. PubMed PMID: 7714718.