Efonidipine
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MedKoo CAT#: 317139

CAS#: 111011-63-3 (free base)

Description: Efonidipine (INN) is a dihydropyridine calcium channel blocker marketed by Shionogi & Co. of Japan. It was launched in 1995, under the brand name Landel (ランデル). The drug blocks both T-type and L-type calcium channels. It has also been studied in atherosclerosis and acute renal failure.

Chemical Structure

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Efonidipine
CAS# 111011-63-3 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317139
Name: Efonidipine
CAS#: 111011-63-3 (free base)
Chemical Formula: C34H38N3O7P
Exact Mass: 631.24
Molecular Weight: 631.670
Elemental Analysis: C, 64.65; H, 6.06; N, 6.65; O, 17.73; P, 4.90

Price and Availability

Size Price Availability Quantity
100mg USD 550 2 weeks
200mg USD 950 2 weeks
500mg USD 1650 2 weeks
1g USD 2650 2 weeks
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Related CAS #: 111011-63-3 (free base)   111011-53-1 (hydrochloride)   111011-76-8 (HCl ethanolate)  

Synonym: NZ-105; NZ 105; NZ105; Efonidipine

IUPAC/Chemical Name: 2-(benzyl(phenyl)amino)ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

InChi Key: NSVFSAJIGAJDMR-UHFFFAOYSA-N

InChi Code: InChI=1S/C34H38N3O7P/c1-24-30(33(38)42-19-18-36(28-15-9-6-10-16-28)21-26-12-7-5-8-13-26)31(27-14-11-17-29(20-27)37(39)40)32(25(2)35-24)45(41)43-22-34(3,4)23-44-45/h5-17,20,31,35H,18-19,21-23H2,1-4H3

SMILES Code: O=C(C1=C(C)NC(C)=C(P2(OCC(C)(C)CO2)=O)C1C3=CC=CC([N+]([O-])=O)=C3)OCCN(CC4=CC=CC=C4)C5=CC=CC=C5

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: Efonidipine (NZ-105) is an L- and T-type calcium channel blocker leading to vasodilation and decreased automaticity of the heart.
In vitro activity: Efonidipine and R(-)-efonidipine significantly increased the production of DHEA-S. On the contrary, angiotensin II alone decrease in the production DHEA-S, and treatment with amlodipine, efonidipine, or R(-)-efonidipine further decreased the production of DHEA-S, but azelnidipine and nifedipine did not exert significant actions on angioptensin II-induced decrease in DHEA-S (Fig. 6B). Reference: Tohoku J Exp Med. 2011 Aug;224(4):263-71. https://pubmed.ncbi.nlm.nih.gov/21757861/
In vivo activity: Diabetes was induced using the neonatal streptozotocin rat model. Treatment with efonidipine showed a significant reduction in post-ischemic brain infract volume, brain hemisphere weight difference, neurological score, Na+-K+ ATPase activity, serum CK-MB, and LDH levels in normoglycemic and hyperglycemic MCAO-induced animals. Reference: J Mol Neurosci. 2021 May 30. https://pubmed.ncbi.nlm.nih.gov/34056691/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 47.49
Ethanol 40.0 63.32

Preparing Stock Solutions

The following data is based on the product molecular weight 631.67 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. Ikeda K, Saito T, Tojo K. Efonidipine, a Ca(2+)-channel blocker, enhances the production of dehydroepiandrosterone sulfate in NCI-H295R human adrenocortical carcinoma cells. Tohoku J Exp Med. 2011 Aug;224(4):263-71. doi: 10.1620/tjem.224.263. PMID: 21757861. 2. Rajput R, Chavda V, Patel SS, Barreto GE, Ashraf GM. Efonidipine Exerts Cerebroprotective Effect by Down-regulation of TGF-β/SMAD-2-Dependent Signaling Pathway in Diabetic Rats. J Mol Neurosci. 2021 May 30. doi: 10.1007/s12031-021-01857-z. Epub ahead of print. PMID: 34056691. 3. Park MH, Son YK, Hong DH, Choi IW, Kim DJ, Lee H, Bang H, Na SH, Li H, Jo SH, Park WS. The Ca(2+) channel inhibitor efonidipine decreases voltage-dependent K(+) channel activity in rabbit coronary arterial smooth muscle cells. Vascul Pharmacol. 2013 Sep-Oct;59(3-4):90-5. doi: 10.1016/j.vph.2013.07.005. Epub 2013 Jul 19. PMID: 23876554.
In vitro protocol: 1. Ikeda K, Saito T, Tojo K. Efonidipine, a Ca(2+)-channel blocker, enhances the production of dehydroepiandrosterone sulfate in NCI-H295R human adrenocortical carcinoma cells. Tohoku J Exp Med. 2011 Aug;224(4):263-71. doi: 10.1620/tjem.224.263. PMID: 21757861.
In vivo protocol: 1. Rajput R, Chavda V, Patel SS, Barreto GE, Ashraf GM. Efonidipine Exerts Cerebroprotective Effect by Down-regulation of TGF-β/SMAD-2-Dependent Signaling Pathway in Diabetic Rats. J Mol Neurosci. 2021 May 30. doi: 10.1007/s12031-021-01857-z. Epub ahead of print. PMID: 34056691. 2. Park MH, Son YK, Hong DH, Choi IW, Kim DJ, Lee H, Bang H, Na SH, Li H, Jo SH, Park WS. The Ca(2+) channel inhibitor efonidipine decreases voltage-dependent K(+) channel activity in rabbit coronary arterial smooth muscle cells. Vascul Pharmacol. 2013 Sep-Oct;59(3-4):90-5. doi: 10.1016/j.vph.2013.07.005. Epub 2013 Jul 19. PMID: 23876554.

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1: Liu M, Zhao H, Tong Y, Zhang D, Wang X, Zhang L, Han J, Liu H. Determination of efonidipine in human plasma by LC-MS/MS for pharmacokinetic applications. J Pharm Biomed Anal. 2014 Nov 11;103C:1-6. doi: 10.1016/j.jpba.2014.11.001. [Epub ahead of print] PubMed PMID: 25462114.

2: Park MH, Son YK, Hong da H, Choi IW, Kim DJ, Lee H, Bang H, Na SH, Li H, Jo SH, Park WS. The Ca(2+) channel inhibitor efonidipine decreases voltage-dependent K(+) channel activity in rabbit coronary arterial smooth muscle cells. Vascul Pharmacol. 2013 Sep-Oct;59(3-4):90-5. doi: 10.1016/j.vph.2013.07.005. Epub 2013 Jul 19. PubMed PMID: 23876554.

3: Hu C, Mori T, Lu Y, Guo Q, Sun Y, Yoneki Y, Ohsaki Y, Nakamichi T, Oba I, Sato E, Ogawa S, Dickinson BC, Chang CJ, Miyata T, Sato H, Ito S. Role of specific T-type calcium channel blocker R(-) efonidipine in the regulation of renal medullary circulation. J Hypertens. 2012 Aug;30(8):1620-31. doi: 10.1097/HJH.0b013e3283550e9f. PubMed PMID: 22688264.

4: Shin J. Efonidipine, another beauty relieving the pressure. Korean Circ J. 2012 Apr;42(4):229-30. doi: 10.4070/kcj.2012.42.4.229. Epub 2012 Apr 26. PubMed PMID: 22563334; PubMed Central PMCID: PMC3341418.

5: Li C, Choi DH, Choi JS. Effects of efonidipine on the pharmacokinetics and pharmacodynamics of repaglinide: possible role of CYP3A4 and P-glycoprotein inhibition by efonidipine. J Pharmacokinet Pharmacodyn. 2012 Feb;39(1):99-108. doi: 10.1007/s10928-011-9234-0. Epub 2012 Jan 1. PubMed PMID: 22210483.

6: Lei B, Hitomi H, Mori T, Nagai Y, Deguchi K, Mori H, Masaki T, Nakano D, Kobori H, Kitaura Y, Nishiyama A. Effect of efonidipine on TGF-β1-induced cardiac fibrosis through Smad2-dependent pathway in rat cardiac fibroblasts. J Pharmacol Sci. 2011;117(2):98-105. Epub 2011 Sep 7. PubMed PMID: 21897055; PubMed Central PMCID: PMC3230079.

7: Ikeda K, Saito T, Tojo K. Efonidipine, a Ca(2+)-channel blocker, enhances the production of dehydroepiandrosterone sulfate in NCI-H295R human adrenocortical carcinoma cells. Tohoku J Exp Med. 2011;224(4):263-71. PubMed PMID: 21757861.

8: Oh IY, Seo MK, Lee HY, Kim SG, Kim KS, Kim WH, Hyon MS, Han KR, Lim SJ, Kim CH. Beneficial Effect of Efonidipine, an L- and T-Type Dual Calcium Channel Blocker, on Heart Rate and Blood Pressure in Patients With Mild-to-Moderate Essential Hypertension. Korean Circ J. 2010 Oct;40(10):514-9. doi: 10.4070/kcj.2010.40.10.514. Epub 2010 Oct 31. PubMed PMID: 21088755; PubMed Central PMCID: PMC2978294.

9: Tanaka H, Namekata I, Ogawa T, Tsuneoka Y, Komikado C, Takahara A, Iida-Tanaka N, Izumi-Nakaseko H, Tsuru H, Adachi-Akahane S. Effects of S(+)-efonidipine on the rabbit sinus node action potential and calcium channel subunits Ca(V)1.2, Ca(V)1.3 and Ca(V)3.1. Eur J Pharmacol. 2010 Dec 15;649(1-3):263-7. doi: 10.1016/j.ejphar.2010.09.014. Epub 2010 Sep 19. PubMed PMID: 20858482.

10: Hayashi K, Saruta T, Goto Y, Ishii M; JATOS Study Group. Impact of renal function on cardiovascular events in elderly hypertensive patients treated with efonidipine. Hypertens Res. 2010 Nov;33(11):1211-20. doi: 10.1038/hr.2010.162. Epub 2010 Sep 16. PubMed PMID: 20844543.

11: Okura T. Efonidipine improves renal function and decreases proteinuria in elderly hypertensive patients in the JATOS study. Hypertens Res. 2010 Nov;33(11):1112-3. doi: 10.1038/hr.2010.150. Epub 2010 Sep 2. PubMed PMID: 20811385.

12: Nakano N, Ishimitsu T, Takahashi T, Inada H, Okamura A, Ohba S, Matsuoka H. Effects of efonidipine, an L- and T-type calcium channel blocker, on the renin-angiotensin-aldosterone system in chronic hemodialysis patients. Int Heart J. 2010 May;51(3):188-92. PubMed PMID: 20558909.

13: Takai S, Jin D, Sakonjo H, Miyazaki M. Combination therapy with irbesartan and efonidipine for attenuation of proteinuria in Dahl salt-sensitive rats. Hypertens Res. 2010 Sep;33(9):953-9. doi: 10.1038/hr.2010.90. Epub 2010 Jun 3. PubMed PMID: 20520612.

14: Sasaki H, Saiki A, Endo K, Ban N, Yamaguchi T, Kawana H, Nagayama D, Ohhira M, Oyama T, Miyashita Y, Shirai K. Protective effects of efonidipine, a T- and L-type calcium channel blocker, on renal function and arterial stiffness in type 2 diabetic patients with hypertension and nephropathy. J Atheroscler Thromb. 2009 Oct;16(5):568-75. Epub 2009 Sep 14. PubMed PMID: 19749494.

15: Tsutamoto T, Tanaka T, Nishiyama K, Yamaji M, Kawahara C, Fujii M, Yamamoto T, Horie M. Long-term effect of efonidipine therapy on plasma aldosterone and left ventricular mass index in patients with essential hypertension. Hypertens Res. 2009 Aug;32(8):670-4. doi: 10.1038/hr.2009.78. Epub 2009 Jun 5. PubMed PMID: 19498438.

16: Ohashi N, Mitamura H, Ogawa S. Development of newer calcium channel antagonists: therapeutic potential of efonidipine in preventing electrical remodelling during atrial fibrillation. Drugs. 2009;69(1):21-30. doi: 10.2165/00003495-200969010-00002. Review. PubMed PMID: 19192934.

17: Morimoto S, Jo F, Maki K, Iwasaka T. Effects of efonidipine hydrochloride on heart rate and circulatory changes due to stress. Clin Exp Hypertens. 2009 Feb;31(1):83-91. doi: 10.1080/10641960802627363. PubMed PMID: 19172462.

18: Wang N, Ye L, Zhao BQ, Yu JX. Spectroscopic studies on the interaction of efonidipine with bovine serum albumin. Braz J Med Biol Res. 2008 Jul;41(7):589-95. PubMed PMID: 18719740.

19: Tanaka H, Komikado C, Namekata I, Nakamura H, Suzuki M, Tsuneoka Y, Shigenobu K, Takahara A. Species difference in the contribution of T-type calcium current to cardiac pacemaking as revealed by r(-)-efonidipine. J Pharmacol Sci. 2008 May;107(1):99-102. Epub 2008 May 3. PubMed PMID: 18460822.

20: Shin MC, Kim CJ, Min BI, Ogawa S, Tanaka E, Akaike N. A selective T-type Ca2+ channel blocker R(-) efonidipine. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jun;377(4-6):411-21. doi: 10.1007/s00210-007-0239-6. Epub 2008 Feb 16. PubMed PMID: 18278483.