Benidipine Hydrochloride | KW-3049 | Coniel | CAS#91599-74-5 | CAS#105979-17-7 | Calcium Antagonist

MedKoo Cat#: 329307 | Name: Benidipine Hydrochloride

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Description:

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

Benidipine Hydrochloride, also known as KW-3049 and Coniel, is a dihydropyridine calcium antagonist used to treat hypertension and angina pectoris. Benidipine Hydrochloride has been reported to reduce oxidative stress.

Chemical Structure

Benidipine Hydrochloride

CAS#91599-74-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 329307

Name: Benidipine Hydrochloride

CAS#: 91599-74-5 (HCl)

Chemical Formula: C28H32ClN3O6

Exact Mass: 0.0000

Molecular Weight: 542.03

Elemental Analysis: C, 62.05; H, 5.95; Cl, 6.54; N, 7.75; O, 17.71

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks

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Related CAS #

105979-17-7 (free base) 91599-74-5 (HCl)

Synonym

Benidipine Hydrochloride; Benidipine HCl; KW-3049; KW 3049; KW3049; Coniel;

IUPAC/Chemical Name

3-((R)-1-benzylpiperidin-3-yl) 5-methyl (R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

InChi Key

KILKDKRQBYMKQX-MIPPOABVSA-N

InChi Code

InChI=1S/C28H31N3O6.ClH/c1-18-24(27(32)36-3)26(21-11-7-12-22(15-21)31(34)35)25(19(2)29-18)28(33)37-23-13-8-14-30(17-23)16-20-9-5-4-6-10-20;/h4-7,9-12,15,23,26,29H,8,13-14,16-17H2,1-3H3;1H/t23-,26-;/m1./s1

SMILES Code

O=C(C1=C(C)NC(C)=C(C(O[C@H]2CN(CC3=CC=CC=C3)CCC2)=O)[C@@H]1C4=CC=CC([N+]([O-])=O)=C4)OC.[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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Benidipine hydrochloride is a dihydropyridine calcium channel blocker.

In vitro activity:

Benidipine caused dose-dependent relaxations on high K+ (80 mM) induced precontraction in mouse airway smooth muscle (ASM), which relied on inhibition of extracellular Ca2+ influx, and 1 μM benidipine totally blocked L-type voltage-dependent Ca2+ channels (LVDCCs) currents in airway smooth muscle cells (ASMCs). Benidipine also showed dose-dependent inhibition of ACh-induced precontraction with or without the LVDCCs blocker nifedipine, and 100 μM benidipine blocked ACh-stimulated Ca2+ influx through not only LVDCCs but also non-selective cation channels (NSCCs). Reference: Life Sci. 2019 Jun 15;227:74-81. https://www.sciencedirect.com/science/article/abs/pii/S002432051930298X?via%3Dihub

In vivo activity:

To examine whether benidipine hydrochloride up-regulates uncoupling protein 3 (UCP3) expression in two skeletal muscles (gastrocnemius and soleus),. Wistar rats were treated orally with benidipine hydrochloride at 4 mg/kg for 7 days. Benidipine reduced body weight and also had a hypotensive effect. In rats treated with benidipine, UCP1 mRNA levels were significantly increased 1.4-fold in BAT, and UCP3 mRNA levels in BAT and gastrocnemius muscle were significantly increased 1.7 and 3.0-fold, respectively, compared with the control rats. There was no difference in UCP3 mRNA levels in soleus muscle between the two groups. These results suggest that benidipine up-regulates not only UCP1 gene expression in BAT but also UCP3 gene expression in BAT and gastrocnemius muscle, which may contribute to thermogenesis in rats. Reference: Endocr J. 2007 Dec;54(5):771-5. https://www.jstage.jst.go.jp/article/endocrj/54/5/54_K06-130/_article

	Solvent	mg/mL	mM
Solubility
	DMSO	23.8	43.87
	DMF	30.0	55.35
	Ethanol	10.0	18.45

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 542.03 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. Yang Y, Chen W, Wen N, Cai C, Liu QH, Shen J. Benidipine, an anti-hypertensive drug, relaxes mouse airway smooth muscle. Life Sci. 2019 Jun 15;227:74-81. doi: 10.1016/j.lfs.2019.04.036. Epub 2019 Apr 16. PMID: 31002920. 2. Sakane N, Kotani K, Hioki C, Yoshida T, Kawada T. Up-regulation of muscle uncoupling protein 3 gene expression by calcium channel blocker, benidipine hydrochloride in rats. Endocr J. 2007 Dec;54(5):771-5. doi: 10.1507/endocrj.k06-130. Epub 2007 Sep 18. PMID: 17878603.

In vitro protocol:

In vivo protocol:

1. Sakane N, Kotani K, Hioki C, Yoshida T, Kawada T. Up-regulation of muscle uncoupling protein 3 gene expression by calcium channel blocker, benidipine hydrochloride in rats. Endocr J. 2007 Dec;54(5):771-5. doi: 10.1507/endocrj.k06-130. Epub 2007 Sep 18. PMID: 17878603.

1: Matsunaka K, Imai M, Sanda K, Yasunami N, Furuhashi A, Atsuta I, Wada H, Ayukawa Y. Therapeutic Effect of Benidipine on Medication-Related Osteonecrosis of the Jaw. Pharmaceuticals (Basel). 2022 Aug 18;15(8):1020. doi: 10.3390/ph15081020. PMID: 36015167; PMCID: PMC9412249. 2: Yang Y, Chen W, Wen N, Cai C, Liu QH, Shen J. Benidipine, an anti- hypertensive drug, relaxes mouse airway smooth muscle. Life Sci. 2019 Jun 15;227:74-81. doi: 10.1016/j.lfs.2019.04.036. Epub 2019 Apr 16. PMID: 31002920. 3: Tomino Y. Renoprotective effects of the L-/T-type calcium channel blocker benidipine in patients with hypertension. Curr Hypertens Rev. 2013 May;9(2):108-14. doi: 10.2174/15734021113099990005. PMID: 23971692. 4: Kocaturk H, Bedir F, Turangezli Ö, Arslan R, Çoban TA, Altuner D, Suleyman H. Effect of adenosine triphosphate, benidipine and their combinations on bevacizumab-induced kidney damage in rats. Adv Clin Exp Med. 2021 Nov;30(11):1175-1183. doi: 10.17219/acem/140440. PMID: 34595851. 5: Koçak MN, Arslan R, Albayrak A, Tekin E, Bayraktar M, Çelik M, Kaya Z, Bekmez H, Tavaci T. An antihypertensive agent benidipine is an effective neuroprotective and antiepileptic agent: an experimental rat study. Neurol Res. 2021 Dec;43(12):1069-1080. doi: 10.1080/01616412.2021.1949685. Epub 2021 Jul 5. PMID: 34225559. 6: Li H, Zhang LK, Li SF, Zhang SF, Wan WW, Zhang YL, Xin QL, Dai K, Hu YY, Wang ZB, Zhu XT, Fang YJ, Cui N, Zhang PH, Yuan C, Lu QB, Bai JY, Deng F, Xiao GF, Liu W, Peng K. Calcium channel blockers reduce severe fever with thrombocytopenia syndrome virus (SFTSV) related fatality. Cell Res. 2019 Sep;29(9):739-753. doi: 10.1038/s41422-019-0214-z. Epub 2019 Aug 23. PMID: 31444469; PMCID: PMC6796935. 7: Yao K, Nagashima K, Miki H. Pharmacological, pharmacokinetic, and clinical properties of benidipine hydrochloride, a novel, long-acting calcium channel blocker. J Pharmacol Sci. 2006 Apr;100(4):243-61. doi: 10.1254/jphs.dtj05001x. Epub 2006 Mar 25. PMID: 16565579. 8: Yue W, Kimura S, Fujisawa Y, Tian R, Li F, Rahman M, Nishiyama A, Fukui T, Abe Y. Benidipine dilates both pre- and post-glomerular arteriole in the canine kidney. Hypertens Res. 2001 Jul;24(4):429-36. doi: 10.1291/hypres.24.429. PMID: 11510756. 9: Yamamoto E, Kataoka K, Dong YF, Nakamura T, Fukuda M, Nako H, Ogawa H, Kim- Mitsuyama S. Benidipine, a dihydropyridine L-type/T-type calcium channel blocker, affords additive benefits for prevention of cardiorenal injury in hypertensive rats. J Hypertens. 2010 Jun;28(6):1321-9. doi: 10.1097/HJH.0b013e3283388045. PMID: 20224431. 10: Ohtani K, Usui S, Kaneko S, Takashima S, Kitano K, Yamamoto K, Okajima M, Furusho H, Takamura M. Benidipine reduces ischemia reperfusion-induced systemic oxidative stress through suppression of aldosterone production in mice. Hypertens Res. 2012 Mar;35(3):287-94. doi: 10.1038/hr.2011.183. Epub 2011 Nov 24. PMID: 22113355. 11: Cakir T, Yucetas SC, Yazici GN, Sunar M, Arslan YK, Suleyman H. Effects of Benidipine Hydrochloride on Ischemia Reperfusion Injury of Rat Brain. Turk Neurosurg. 2021;31(3):310-317. doi: 10.5137/1019-5149.JTN.27372-19.3. PMID: 32091117. 12: Sunwoo YE, Nguyen PTT, Chien CM, Ryu JY, Shon J, Shin JG. Effect of rifampin on enantioselective disposition and anti-hypertensive effect of benidipine. Br J Clin Pharmacol. 2019 Apr;85(4):737-745. doi: 10.1111/bcp.13848. Epub 2019 Jan 30. PMID: 30589098; PMCID: PMC6422640. 13: Akbayram S, Akgün C, Doğan M, Geylani H, Sarı N, Taşkın AG, Caksen H. Benidipine hydrochloride intoxication in a child. J Emerg Med. 2012 Jun;42(6):700-1. doi: 10.1016/j.jemermed.2010.05.085. Epub 2010 Sep 19. PMID: 20851552. 14: Sofy AA, Abdelsattar AT, Mohammed OM, Shareef MA, Alamodi AA, Nso N, Payton M, Masoud AT. Amlodipine Compared with Benidipine in the Management of Hypertension: A Systematic Review and Meta-Analysis. High Blood Press Cardiovasc Prev. 2020 Dec;27(6):527-537. doi: 10.1007/s40292-020-00412-y. Epub 2020 Oct 1. PMID: 33001356. 15: Matsubara M, Yao K, Hasegawa K. Benidipine, a dihydropyridine-calcium channel blocker, inhibits lysophosphatidylcholine-induced endothelial injury via stimulation of nitric oxide release. Pharmacol Res. 2006 Jan;53(1):35-43. doi: 10.1016/j.phrs.2005.08.006. Epub 2005 Sep 19. PMID: 16172001. 16: Matsubara M, Akizuki O, Ikeda J, Saeki K, Yao K, Sasaki K. Benidipine, an anti-hypertensive drug, inhibits reactive oxygen species production in polymorphonuclear leukocytes and oxidative stress in salt-loaded stroke-prone spontaneously hypertensive rats. Eur J Pharmacol. 2008 Feb 2;580(1-2):201-13. doi: 10.1016/j.ejphar.2007.10.072. Epub 2007 Nov 1. PMID: 18048030. 17: Mathew SK, Naik GS, Peedicayil J. Inhibition by Benidipine of Contractility of Isolated Proximal and Distal Caprine Ureter. Int J Appl Basic Med Res. 2017 Jul-Sep;7(3):155-159. doi: 10.4103/ijabmr.IJABMR_87_16. PMID: 28904913; PMCID: PMC5590376. 18: Kazama I, Maruyama Y, Matsubara M. Benidipine persistently inhibits delayed rectifier K(+)-channel currents in murine thymocytes. Immunopharmacol Immunotoxicol. 2013 Feb;35(1):28-33. doi: 10.3109/08923973.2012.723011. Epub 2012 Sep 17. PMID: 22978806. 19: Hou HT, Wang J, Wang ZQ, Liu XC, Marinko M, Novakovic A, Yang Q, He GW. Effect of Benidipine in Human Internal Mammary Artery and Clinical Implications. Ann Thorac Surg. 2016 May;101(5):1789-95. doi: 10.1016/j.athoracsur.2015.10.029. Epub 2015 Dec 23. PMID: 26707005. 20: Abe M, Okada K, Maruyama N, Matsumoto S, Maruyama T, Fujita T, Matsumoto K, Soma M. Benidipine reduces albuminuria and plasma aldosterone in mild-to- moderate stage chronic kidney disease with albuminuria. Hypertens Res. 2011 Feb;34(2):268-73. doi: 10.1038/hr.2010.221. Epub 2010 Dec 2. PMID: 21124330.