Pilsicainide HCl
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MedKoo CAT#: 329454

CAS#: 88069-49-2 (HCl)

Description: Pilsicainide, also known as SUN 1165, is a drug used clinically in Japan to treat cardiac arrhythmias. It functions by blocking the fast inward movement of sodium ions through the Nav1.5 sodium channel that contributes to the rapid depolarization characteristic of phase 0 in the cardiac action potential. Pilsicainide is a pure sodium channel blocker, meaning it does not significantly affect any other cardiac channels including potassium and calcium channels.

Chemical Structure

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Pilsicainide HCl
CAS# 88069-49-2 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329454
Name: Pilsicainide HCl
CAS#: 88069-49-2 (HCl)
Chemical Formula: C17H25ClN2O
Exact Mass: 0.00
Molecular Weight: 308.850
Elemental Analysis: C, 66.11; H, 8.16; Cl, 11.48; N, 9.07; O, 5.18

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Related CAS #: 88069-67-4 (free base); 88069-49-2 (HCl)  

Synonym: Pilsicainide hydrochloride; SUN 1165; SUN-1165; SUN1165.

IUPAC/Chemical Name: N-(2,6-dimethylphenyl)-2-(tetrahydro-1H-pyrrolizin-7a(5H)-yl)acetamide hydrochloride

InChi Key: NZOSVDHCTCLGEB-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H24N2O.ClH/c1-13-6-3-7-14(2)16(13)18-15(20)12-17-8-4-10-19(17)11-5-9-17;/h3,6-7H,4-5,8-12H2,1-2H3,(H,18,20);1H

SMILES Code: O=C(NC1=C(C)C=CC=C1C)CC23CCCN2CCC3.[H]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

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: Related CAS# 88069-49-2 (Pilsicainide hydrochloride) 88069-67-4 (Pilsicainide free base)

Product Data:
Product Data
Instruction:
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Biological target: Pilsicainide hydrochloride (SUN-1165) is an orally active sodium channel blocker and potent class Ic antiarrhythmic agent.
In vitro activity: Pilsicainide exhibited tonic and use-dependent effects comparable to those of mexiletine and flecainide on hNav1.4 channels. These use-dependent effects were abolished in the mutations F1586C and Y1593C within segment 6 of domain IV, suggesting that the interaction of pilsicainide with these residues is critical for its local anaesthetic action. Effects of pilsicainide were similar on skeletal muscle hNav1.4, brain hNav1.1 and heart hNav1.5 channels. The myotonic R1448C and G1306E hNav1.4 mutants were more and less sensitive to pilsicainide, respectively, due to mutation-induced gating modifications. Reference: Br J Pharmacol. 2010 Jul;160(6):1521-33. https://pubmed.ncbi.nlm.nih.gov/20590641/
In vivo activity: This study explored the relationship between the reduction of sodium channel availability with a pure SCB (pilsicainide or tetrodotoxin) and atrial PRR using the left atrial appendage from male guinea pigs (each group, n = 3~10). Employing a standard microelectrode technique, this study evaluated APD measured at 90% repolarization (APD(90)) and the sodium channel availability, judged from the maximal rate of rise of action potential (Vmax). At a 500-msec basic cycle length (BCL), pilsicainide prolonged atrial ERP assessed by a single extra-stimulus in response to the decrement of the Vmax in a dose-dependent manner without affecting APD(90). Furthermore, pilsicainide increased the ERP and decreased the Vmax in a rate-dependent manner without APD(90) prolongation at a shorter BCL (200 msec). Reference: Tohoku J Exp Med. 2011 Sep;225(1):35-42. https://pubmed.ncbi.nlm.nih.gov/21869589/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 64.76
DMSO 25.0 80.95
Ethanol 25.0 80.95
PBS (pH 7.2) 10.0 32.38

Preparing Stock Solutions

The following data is based on the product molecular weight 308.85 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. Desaphy JF, Dipalma A, Costanza T, Bruno C, Lentini G, Franchini C, George A, Conte Camerino D. Molecular determinants of state-dependent block of voltage-gated sodium channels by pilsicainide. Br J Pharmacol. 2010 Jul;160(6):1521-33. doi: 10.1111/j.1476-5381.2010.00816.x. PMID: 20590641; PMCID: PMC2938822. 2. Wu LM, Orikabe M, Hirano Y, Kawano S, Hiraoka M. Effects of Na+ channel blocker, pilsicainide, on HERG current expressed in HEK-293 cells. J Cardiovasc Pharmacol. 2003 Sep;42(3):410-8. doi: 10.1097/00005344-200309000-00013. PMID: 12960687. 3. Fukuda K, Watanabe J, Yagi T, Wakayama Y, Nakano M, Kondo M, Kumagai K, Miura M, Shirato K, Shimokawa H. A sodium channel blocker, pilsicainide, produces atrial post-repolarization refractoriness through the reduction of sodium channel availability. Tohoku J Exp Med. 2011 Sep;225(1):35-42. doi: 10.1620/tjem.225.35. PMID: 21869589. 4. Yamakawa M, Sunagawa M, Shimabukuro M, Higa N, Takasu N, Kosugi T. Effect of sodium channel blocker, pilsicainide hydrochloride, on net inward current of atrial myocytes in thyroid hormone toxicosis rats. Thyroid. 2005 Jul;15(7):653-9. doi: 10.1089/thy.2005.15.653. PMID: 16053380.
In vitro protocol: 1. Desaphy JF, Dipalma A, Costanza T, Bruno C, Lentini G, Franchini C, George A, Conte Camerino D. Molecular determinants of state-dependent block of voltage-gated sodium channels by pilsicainide. Br J Pharmacol. 2010 Jul;160(6):1521-33. doi: 10.1111/j.1476-5381.2010.00816.x. PMID: 20590641; PMCID: PMC2938822. 2. Wu LM, Orikabe M, Hirano Y, Kawano S, Hiraoka M. Effects of Na+ channel blocker, pilsicainide, on HERG current expressed in HEK-293 cells. J Cardiovasc Pharmacol. 2003 Sep;42(3):410-8. doi: 10.1097/00005344-200309000-00013. PMID: 12960687.
In vivo protocol: 1. Fukuda K, Watanabe J, Yagi T, Wakayama Y, Nakano M, Kondo M, Kumagai K, Miura M, Shirato K, Shimokawa H. A sodium channel blocker, pilsicainide, produces atrial post-repolarization refractoriness through the reduction of sodium channel availability. Tohoku J Exp Med. 2011 Sep;225(1):35-42. doi: 10.1620/tjem.225.35. PMID: 21869589. 2. Yamakawa M, Sunagawa M, Shimabukuro M, Higa N, Takasu N, Kosugi T. Effect of sodium channel blocker, pilsicainide hydrochloride, on net inward current of atrial myocytes in thyroid hormone toxicosis rats. Thyroid. 2005 Jul;15(7):653-9. doi: 10.1089/thy.2005.15.653. PMID: 16053380.

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1: Yamasaki H, Tada H, Sekiguchi Y, Aonuma K. Right coronary cusp as a new window of ablation for pilsicainide-induced ventricular premature contractions in a patient with Brugada syndrome. Heart Vessels. 2016 Aug;31(8):1397-401. doi: 10.1007/s00380-015-0760-3. PubMed PMID: 26510553.

2: Shimizu M, Hashiguchi M, Shiga T, Nakamura K, Tamura HO, Mochizuki M. Quantitation of pilsicainide in microscale samples of human biological fluids using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Mar 15;985:172-9. doi: 10.1016/j.jchromb.2015.01.013. PubMed PMID: 25687803.

3: Nakatani S, Taniike M, Makino N, Egami Y, Shutta R, Tanouchi J, Nishino M. A Case of Sudden Cardiac Death due to Pilsicainide-Induced Torsades de Pointes. Korean Circ J. 2014 Mar;44(2):122-4. doi: 10.4070/kcj.2014.44.2.122. PubMed PMID: 24653743; PubMed Central PMCID: PMC3958607.

4: Qiu Q, Liu W, Li J, Wei Y, Yang K, Suo W, Wu W, Du H, Zhang Y, Zhao G, Zhou Z, Zheng Y, Lin Y. Pharmacokinetics of pilsicainide hydrochloride for injection in healthy Chinese volunteers: a randomized, parallel-group, open-label, single-dose study. Clin Ther. 2014 Feb 1;36(2):255-63. doi: 10.1016/j.clinthera.2013.12.015. PubMed PMID: 24480637.

5: Nakamura K, Fukami N. Altered responses to vasopressors of a patient medicated with carvedilol, pilsicainide and enalapril. J Anesth. 2014 Aug;28(4):625-7. doi: 10.1007/s00540-013-1762-x. PubMed PMID: 24366327.

6: Takahara A, Suzuki S, Hagiwara M, Nozaki S, Sugiyama A. Electrophysiological effects of an anti-influenza drug oseltamivir on the guinea-pig atrium: comparison with those of pilsicainide. Biol Pharm Bull. 2013;36(10):1650-2. PubMed PMID: 24088258.

7: Takahara A, Takeda K, Tsuneoka Y, Hagiwara M, Namekata I, Tanaka H. Electrophysiological effects of the class Ic antiarrhythmic drug pilsicainide on the guinea-pig pulmonary vein myocardium. J Pharmacol Sci. 2012;118(4):506-11. PubMed PMID: 22466963.

8: Kaneko Y, Nakajima T, Kato T, Kurabayashi M. Pilsicainide-induced polymorphic ventricular tachycardia. Intern Med. 2012;51(4):443-4. PubMed PMID: 22333385.

9: Fukuda K, Watanabe J, Yagi T, Wakayama Y, Nakano M, Kondo M, Kumagai K, Miura M, Shirato K, Shimokawa H. A sodium channel blocker, pilsicainide, produces atrial post-repolarization refractoriness through the reduction of sodium channel availability. Tohoku J Exp Med. 2011;225(1):35-42. PubMed PMID: 21869589.

10: Kajimoto K, Imai T, Minami Y, Kasanuki H. Comparison of acute reduction in left ventricular outflow tract pressure gradient in obstructive hypertrophic cardiomyopathy by disopyramide versus pilsicainide versus cibenzoline. Am J Cardiol. 2010 Nov 1;106(9):1307-12. doi: 10.1016/j.amjcard.2010.06.059. PubMed PMID: 21029829.

11: Desaphy JF, Dipalma A, Costanza T, Bruno C, Lentini G, Franchini C, George A, Conte Camerino D. Molecular determinants of state-dependent block of voltage-gated sodium channels by pilsicainide. Br J Pharmacol. 2010 Jul;160(6):1521-33. doi: 10.1111/j.1476-5381.2010.00816.x. PubMed PMID: 20590641; PubMed Central PMCID: PMC2938822.

12: Plosker GL. Pilsicainide. Drugs. 2010 Mar 5;70(4):455-67. doi: 10.2165/11204960-000000000-00000. Review. PubMed PMID: 20205487.

13: Iwasaki H, Takahara A, Nakamura Y, Satoh Y, Nagai T, Shinkai N, Sugiyama A. Simultaneous assessment of pharmacokinetics of pilsicainide transdermal patch and its electropharmacological effects on atria of chronic atrioventricular block dogs. J Pharmacol Sci. 2009 Jul;110(3):410-4. PubMed PMID: 19574726.

14: Chinushi M, Tagawa M, Izumi D, Furushima H, Aizawa Y. Pilsicainide-induced ST segment elevation and ST segment depression in two patients with variant forms of Brugada-type electrocardiographic abnormalities. Pacing Clin Electrophysiol. 2009 Jun;32(6):811-5. doi: 10.1111/j.1540-8159.2009.02371.x. PubMed PMID: 19545347.

15: Kim BH, Kim JR, Lim KS, Kim JW, Kim KP, Hong JH, Jang IJ, Shin SG, Yu KS, Tanaka T. An open-label, single-dose, parallel-group, dose-increasing study comparing the pharmacokinetics and tolerability of pilsicainide hydrochloride in healthy Korean and Japanese male subjects. Clin Ther. 2009 Mar;31(3):609-18. doi: 10.1016/j.clinthera.2009.03.015. PubMed PMID: 19393851.

16: Horiuchi D, Iwasa A, Sasaki K, Owada S, Kimura M, Sasaki S, Okumura K. Effect of pilsicainide on dominant frequency in the right and left atria and pulmonary veins during atrial fibrillation: association with its atrial fibrillation terminating effect. Eur J Pharmacol. 2009 Apr 17;608(1-3):54-61. doi: 10.1016/j.ejphar.2009.02.040. PubMed PMID: 19268659.

17: Oe K, Nagata M, Mori K. Pilsicainide intoxication presenting as left ventricular dyssynchrony in a patient on hemodialysis. J Cardiol. 2009 Feb;53(1):136-9. doi: 10.1016/j.jjcc.2008.07.002. PubMed PMID: 19167649.

18: Komatsu T, Tachibana H, Sato Y, Ozawa M, Ohshima K, Orii M, Kunigida F, Nakamura M. A randomized study on the efficacy of intravenous cibenzoline and pilsicainide administered prior to electrical cardioversion in patients with lone paroxysmal and persistent atrial fibrillation. J Cardiol. 2009 Feb;53(1):35-42. doi: 10.1016/j.jjcc.2008.08.007. PubMed PMID: 19167636.

19: Hikiji W, Kudo K, Nishida N, Ishida T, Usumoto Y, Tsuji A, Ikeda N. Acute fatal poisoning with pilsicainide and atenolol. Int J Legal Med. 2008 Nov;122(6):503-6. doi: 10.1007/s00414-008-0269-8. PubMed PMID: 18642016.

20: Ueyama T, Shimizu A, Esato M, Yoshiga Y, Sawa A, Suzuki S, Sugi N, Matsuzaki M. Pilsicainide-induced Brugada-type ECG and ventricular arrhythmias originating from the left posterior fascicle in a case with Brugada syndrome associated with idiopathic left ventricular tachycardia. Europace. 2008 Jan;10(1):86-90. PubMed PMID: 18037690.