Bepridil hydrochloride | CAS# 68099-86-5 | Calcium channel protein inhibitor

MedKoo Cat#: 317318 | Name: Bepridil HCl

Description:

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

Bepridil Hydrochloride is the hydrochloride salt form of bepridil, a calcium antagonist and class IV anti-arrhythmic agent. Bepridil hydrochloride blocks calcium entry through membranous calcium channels of coronary and peripheral vascular smooth muscle, thereby dilating coronary arteries and peripheral arterioles. This drug is used to treat chronic stable and variant angina pectoris. Bepridil hydrochloride has antihypertensive and selective anti-arrhythmia activities and acts as a calmodulin antagonist.

Chemical Structure

Bepridil HCl

CAS#68099-86-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 317318

Name: Bepridil HCl

CAS#: 68099-86-5 (HCl)

Chemical Formula: C24H33ClN2O

Exact Mass: 0.0000

Molecular Weight: 400.99

Elemental Analysis: C, 71.89; H, 8.30; Cl, 8.84; N, 6.99; O, 3.99

Price and Availability

Size	Price	Availability
100mg	USD 450.00	2 Weeks
200mg	USD 750.00	2 Weeks
500mg	USD 1,550.00	2 Weeks
1g	USD 2,650.00	2 Weeks
2g	USD 4,650.00	2 Weeks
5g	USD 7,450.00	2 Weeks

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Related CAS #

64706-54-3 (free base) 68099-86-5 (HCl) 74764-40-2 (HCl hydrate) 99239-96-0 (S-isomer HCl) 110143-75-4 (S-isomer) 110143-74-3 (R-isomer)

Synonym

CERM 1978; CERM-1978; CERM1978; Angopril, Bepadin, Bepridil HCl, Bepridil hydrochloride;

IUPAC/Chemical Name

1-Pyrrolideneethanamine, beta-((2-methylpropoxy)methyl)-N-phenyl-N-(phenylmethyl)-, hydrochloride

InChi Key

IHYCZMGXKHVACP-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H32N2O.ClH/c1-20(2)18-27-19-22(24-14-9-15-25-24)17-26(23-12-7-4-8-13-23)16-21-10-5-3-6-11-21;/h3-8,10-13,20,22H,9,14-19H2,1-2H3;1H

SMILES Code

CC(C)COCC(C1=NCCC1)CN(C2=CC=CC=C2)CC3=CC=CC=C3.[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, 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:

Bepridil hydrochloride (CERM 1978) is a calcium channel blocker.

In vitro activity:

Bepridil treatment significantly reduced the viability of primary chronic lymphocytic leukemia (CLL) cells at a 2.5 μM concentration (Fig. 3 a). Specifically, viability significantly decreased to 34 ± 22.2% compared to 57 ± 21.6% of the vehicle control in 66 CLL samples tested (p <0.001) (Fig. 3 b; Supporting Information Table S1). Conversely, bepridil did not affect the viability of T cells from CLL patients nor the viability of B and T cells from healthy donors, demonstrating a selective activity against neoplastic B cells compared to normal hematopoietic cells (Figs. 3 b and 3 c). Reference: Int J Cancer. 2018 Aug 15;143(4):958-970. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6055653/

In vivo activity:

NSG mice were treated with bepridil to determine its in vivo effects on xenografted CLL cells. Bepridil 5 mg/kg was intraperitoneal (i.p.) administered daily over a 20-day period starting 3 days after CLL injection. Flow cytometry analysis revealed a statistically significant decrease in human CD45 + CD19 + CD5+ percentage in the spleen of bepridil-treated mice compared to vehicle (1.9 ± 1% vs. 10.8 ± 10%, N = 13, p < 0.05) (Fig. 6 c). Furthermore, immunohistochemical analyses showed significantly reduced splenic engraftment of human CD20 positive cells in treated mice (Fig. 6 d). Bepridil significantly increased the expression of Annexin V on human CD45 + CD19 + CD5+ B cells compared to vehicle (Fig. 6 e; 66%±20.8 vs. 45.7%±24.3, p < 0.01), consistent with a high rate of apoptosis in vivo. Reference: Int J Cancer. 2018 Aug 15;143(4):958-970. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6055653/

	Solvent	mg/mL	mM
Solubility
	DMSO	59.1	147.34
	DMF	20.0	49.88
	Ethanol	25.0	62.35
	Ethanol:PBS (pH 7.2) (1:2)	0.3	0.75

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 400.99 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.

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. Vatansever EC, Yang KS, Drelich AK, Kratch KC, Cho CC, Kempaiah KR, Hsu JC, Mellott DM, Xu S, Tseng CK, Liu WR. Bepridil is potent against SARS-CoV-2 in vitro. Proc Natl Acad Sci U S A. 2021 Mar 9;118(10):e2012201118. doi: 10.1073/pnas.2012201118. PMID: 33597253; PMCID: PMC7958448. 2. Baldoni S, Del Papa B, Dorillo E, Aureli P, De Falco F, Rompietti C, Sorcini D, Varasano E, Cecchini D, Zei T, Di Tommaso A, Rosati E, Alexe G, Roti G, Stegmaier K, Di Ianni M, Falzetti F, Sportoletti P. Bepridil exhibits anti-leukemic activity associated with NOTCH1 pathway inhibition in chronic lymphocytic leukemia. Int J Cancer. 2018 Aug 15;143(4):958-970. doi: 10.1002/ijc.31355. Epub 2018 Mar 23. PMID: 29508386; PMCID: PMC6055653. 3. DeWald LE, Dyall J, Sword JM, Torzewski L, Zhou H, Postnikova E, Kollins E, Alexander I, Gross R, Cong Y, Gerhardt DM, Johnson RF, Olinger GG Jr, Holbrook MR, Hensley LE, Jahrling PB. The Calcium Channel Blocker Bepridil Demonstrates Efficacy in the Murine Model of Marburg Virus Disease. J Infect Dis. 2018 Nov 22;218(suppl_5):S588-S591. doi: 10.1093/infdis/jiy332. PMID: 29982632; PMCID: PMC6249584.

In vitro protocol:

In vivo protocol:

1. Baldoni S, Del Papa B, Dorillo E, Aureli P, De Falco F, Rompietti C, Sorcini D, Varasano E, Cecchini D, Zei T, Di Tommaso A, Rosati E, Alexe G, Roti G, Stegmaier K, Di Ianni M, Falzetti F, Sportoletti P. Bepridil exhibits anti-leukemic activity associated with NOTCH1 pathway inhibition in chronic lymphocytic leukemia. Int J Cancer. 2018 Aug 15;143(4):958-970. doi: 10.1002/ijc.31355. Epub 2018 Mar 23. PMID: 29508386; PMCID: PMC6055653. 2. DeWald LE, Dyall J, Sword JM, Torzewski L, Zhou H, Postnikova E, Kollins E, Alexander I, Gross R, Cong Y, Gerhardt DM, Johnson RF, Olinger GG Jr, Holbrook MR, Hensley LE, Jahrling PB. The Calcium Channel Blocker Bepridil Demonstrates Efficacy in the Murine Model of Marburg Virus Disease. J Infect Dis. 2018 Nov 22;218(suppl_5):S588-S591. doi: 10.1093/infdis/jiy332. PMID: 29982632; PMCID: PMC6249584.

1: Noda K, Gotoh Y, Tanioka S, Narayama Y, Kobayashi M, Iwai S, Katoh N, Tadano K. The relationship between the plasma concentration of bepridil and its efficacy in the treatment of atrial fibrillation in Japanese patients. Biol Pharm Bull. 2012;35(5):672-6. PubMed PMID: 22687400. 2: Kang J, Chen XL, Ji J, Lei Q, Rampe D. Ca²⁺ channel activators reveal differential L-type Ca²⁺ channel pharmacology between native and stem cell-derived cardiomyocytes. J Pharmacol Exp Ther. 2012 May;341(2):510-7. doi: 10.1124/jpet.112.192609. Epub 2012 Feb 21. PubMed PMID: 22353878. 3: Noda K, Narayama Y, Goto Y, Kobayashi M, Kuronuma H, Iwai S, Itoh K, Katoh N, Tadano K. An LC method for quantifying bepridil in human plasma using 1-naphthol as the internal standard. J Chromatogr Sci. 2011 Aug;49(7):519-23. PubMed PMID: 21801483. 4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Jul-Aug;32(6):437-61. doi: 10.1358/mf.2010.32.6.1538165. PubMed PMID: 20852754. 5: Peak E, Chalmers IW, Hoffmann KF. Development and validation of a quantitative, high-throughput, fluorescent-based bioassay to detect schistosoma viability. PLoS Negl Trop Dis. 2010 Jul 27;4(7):e759. doi: 10.1371/journal.pntd.0000759. PubMed PMID: 20668553; PubMed Central PMCID: PMC2910722. 6: Márián T, Szabó-Péli J, Németh E, Trón L, Friedlander E, Szabó A, Balkay L, Veress G, Krasznai Z. Na+/Ca2+ exchanger inhibitors modify the accumulation of tumor-diagnostic PET tracers in cancer cells. Eur J Pharm Sci. 2007 Jan;30(1):56-63. Epub 2006 Oct 20. PubMed PMID: 17125978. 7: Yasuda M, Nakazato Y, Sasaki A, Kawano Y, Nakazato K, Tokano T, Daida H. Clinical evaluation of adverse effects during bepridil administration for atrial fibrillation and flutter. Circ J. 2006 Jun;70(6):662-6. PubMed PMID: 16723784. 8: Krasznai Z, Krasznai ZT, Morisawa M, Bazsáné ZK, Hernádi Z, Fazekas Z, Trón L, Goda K, Márián T. Role of the Na+/Ca2+ exchanger in calcium homeostasis and human sperm motility regulation. Cell Motil Cytoskeleton. 2006 Feb;63(2):66-76. PubMed PMID: 16374831. 9: Saija A, Tomaino A, Pellegrino ML, Giuffrida N, Trombetta D, Castelli F. In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G. Life Sci. 2001 Feb 9;68(12):1351-66. PubMed PMID: 11388688. 10: Brude IR, Drevon CA, Viken K, Arnstad JE, Valnes KN, Nenseter MS. Doxazosin treatment and peroxidation of low-density lipoprotein among male hypertensive subjects: in vitro and ex vivo studies. Biochem Pharmacol. 1999 Jul 1;58(1):183-91. PubMed PMID: 10403533. 11: Guo Q, Zhao B, Shen S, Hou J, Hu J, Xin W. ESR study on the structure-antioxidant activity relationship of tea catechins and their epimers. Biochim Biophys Acta. 1999 Mar 14;1427(1):13-23. PubMed PMID: 10082983. 12: Nenseter MS, Halvorsen B, Rosvold O, Rustan AC, Drevon CA. Paracetamol inhibits copper ion-induced, azo compound-initiated, and mononuclear cell-mediated oxidative modification of LDL. Arterioscler Thromb Vasc Biol. 1995 Sep;15(9):1338-44. PubMed PMID: 7670947. 13: Awni WM, Halstenson CE, Nayak RK, Opsahl JA, Desiraju RK, Minn FL, Matzke GR. Pharmacokinetics of bepridil and two of its metabolites in patients with end-stage renal disease. J Clin Pharmacol. 1995 Apr;35(4):379-83. PubMed PMID: 7650227. 14: Pritchard JF, Matzke GR, Opsahl JA, Halstenson CE, Nayak RK. Effects of hemodialysis on plasma protein binding of bepridil. J Clin Pharmacol. 1995 Feb;35(2):137-41. PubMed PMID: 7751422. 15: Dinis TC, Maderia VM, Almeida LM. Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch Biochem Biophys. 1994 Nov 15;315(1):161-9. PubMed PMID: 7979394. 16: Makkar RR, Fromm BS, Steinman RT, Meissner MD, Lehmann MH. Female gender as a risk factor for torsades de pointes associated with cardiovascular drugs. JAMA. 1993 Dec 1;270(21):2590-7. PubMed PMID: 8230644. 17: Zusman RM, Higgins J, Christensen D, Boucher CA. Bepridil improves left ventricular performance in patients with angina pectoris. J Cardiovasc Pharmacol. 1993 Sep;22(3):474-80. PubMed PMID: 7504141. 18: Katsumata K, Katsumata K Jr, Katsumata Y. Protective effect of diltiazem hydrochloride on the occurrence of alloxan- or streptozotocin-induced diabetes in rats. Horm Metab Res. 1992 Nov;24(11):508-10. PubMed PMID: 1452115. 19: Frishman WH. Comparative efficacy and concomitant use of bepridil and beta blockers in the management of angina pectoris. Am J Cardiol. 1992 Apr 9;69(11):50D-55D. PubMed PMID: 1553892. 20: Shapiro W. Comparative efficacy of bepridil versus placebo in angina pectoris: treatment and withdrawal studies. Am J Cardiol. 1992 Apr 9;69(11):43D-49D. PubMed PMID: 1553891.