Pranidipine | CAS#99522-79-9 | calcium channel blocker

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

MedKoo CAT#: 319565

CAS#: 99522-79-9

Description: Pranidipine, also known as OPC-13340 and FRC 8411, is a potent and selective calcium channel blocker potentially for the treatment of angina pectoris and hypertension. Pranidipine enhances nitric oxide-induced vascular relaxation. pranidipine prevents the left ventricular remodeling process accompanied by systolic and diastolic dysfunction, and inhibits abnormal cardiac gene expression after myocardial infarction.

Chemical Structure

Pranidipine

CAS# 99522-79-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319565
Name: Pranidipine
CAS#: 99522-79-9
Chemical Formula: C25H24N2O6
Exact Mass: 448.16
Molecular Weight: 448.475
Elemental Analysis: C, 66.95; H, 5.39; N, 6.25; O, 21.40

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 295
50mg	USD 1050
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: OPC-13340; OPC 13340; OPC13340; FRC 8411; FRC-8411; FRC8411; Pranidipine.

IUPAC/Chemical Name: 3-cinnamyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

InChi Key: XTFPDGZNWTZCMF-DHZHZOJOSA-N

InChi Code: InChI=1S/C25H24N2O6/c1-16-21(24(28)32-3)23(19-12-7-13-20(15-19)27(30)31)22(17(2)26-16)25(29)33-14-8-11-18-9-5-4-6-10-18/h4-13,15,23,26H,14H2,1-3H3/b11-8+

SMILES Code: O=C(C1=C(C)NC(C)=C(C(OC)=O)C1C2=CC=CC([N+]([O-])=O)=C2)OC/C=C/C3=CC=CC=C3

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:

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Biological target:	Pranidipine (OPC-13340) is a potent, long acting 1,4-dihydropyridine calcium channel blocker with antihypertensive activity.
In vitro activity:	Pranidipine also prolonged glyceryl trinitrate-induced relaxation in the endothelium denuded rat aorta. Furthermore, pranidipine enhanced relaxation of the aorta induced by glyceryl trinitrate even in the presence of methylene blue, a guanylyl cyclase inhibitor. This action was not modified by iberiotoxin or by charybdotoxin, two inhibitors of the calcium-activated potassium channel. The results strongly suggest that pranidipine enhances cyclic GMP-independent NO-induced relaxation of smooth muscle by a mechanism other than through NO-induced hyperpolarization. Reference: Mol Cell Biochem. 1998 Jan;178(1-2):335-43. https://pubmed.ncbi.nlm.nih.gov/9546618/
In vivo activity:	Among 6 compounds tested, (OPC-13340, nifedipine, nitrendipine, nisoldipine, nicardipine and diltiazem), OPC-13340 was the most potent and long-acting when administered orally to spontaneously hypertensive rats (SHR). Tachycardia after administration of OPC-13340 was less or diminished earlier than that of nicardipine. Oral administration of OPC-13340 (3 mg/kg) once daily for 13 days did not cause any rebound phenomena in SHR. The compound inhibited Ca- or K-induced contractions in isolated rat aorta and shortened action potential duration in guinea pig papillary muscle, suggesting Ca channel blocking action. OPC-13340 might be useful as a drug for once-daily therapy of essential hypertension. Reference: J Cardiovasc Pharmacol. 1990 May;15(5):836-44. https://pubmed.ncbi.nlm.nih.gov/1692946/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	180.0	401.36
	Ethanol	2.0	4.46

Preparing Stock Solutions

The following data is based on the product molecular weight 448.48 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. Koshita M, Takano H, Nakahira Y, Suzuki H. Pranidipine enhances relaxation produced by endothelium-derived relaxing factor in carotid artery. Eur J Pharmacol. 1999 Dec 3;385(2-3):191-7. doi: 10.1016/s0014-2999(99)00702-5. PMID: 10607875. 2. Mori T, Takeuchi T, Ohura M, Miyakoda G, Fujiki H, Orito K, Yoshida K, Hirano T, Yamamura Y, Sumida T, Nakaya Y, Satake H, Hata F. Pranidipine, a new 1,4-dihydropyridine calcium channel blocker, enhances cyclic GMP-independent nitric oxide-induced relaxation of the rat aorta. Mol Cell Biochem. 1998 Jan;178(1-2):335-43. doi: 10.1023/a:1006827801386. PMID: 9546618. 3. Veeraveedu PT, Watanabe K, Ma M, Gurusamy N, Palaniyandi SS, Wen J, Prakash P, Wahed MI, Kamal FA, Mito S, Kunisaki M, Kodama M, Aizawa Y. Comparative effects of pranidipine with amlodipine in rats with heart failure. Pharmacology. 2006;77(1):1-10. doi: 10.1159/000091746. Epub 2006 Feb 27. PMID: 16508340. 4. Nakayama N, Ikezono K, Mori T, Yamashita S, Nakayama S, Tanaka Y, Hosokawa T, Minami Y, Masutani K, Yamamura Y, et al. Antihypertensive activity of OPC-13340, a new potent and long-acting dihydropyridine calcium antagonist, in rats. J Cardiovasc Pharmacol. 1990 May;15(5):836-44. doi: 10.1097/00005344-199005000-00021. PMID: 1692946.
In vitro protocol:	1. Koshita M, Takano H, Nakahira Y, Suzuki H. Pranidipine enhances relaxation produced by endothelium-derived relaxing factor in carotid artery. Eur J Pharmacol. 1999 Dec 3;385(2-3):191-7. doi: 10.1016/s0014-2999(99)00702-5. PMID: 10607875. 2. Mori T, Takeuchi T, Ohura M, Miyakoda G, Fujiki H, Orito K, Yoshida K, Hirano T, Yamamura Y, Sumida T, Nakaya Y, Satake H, Hata F. Pranidipine, a new 1,4-dihydropyridine calcium channel blocker, enhances cyclic GMP-independent nitric oxide-induced relaxation of the rat aorta. Mol Cell Biochem. 1998 Jan;178(1-2):335-43. doi: 10.1023/a:1006827801386. PMID: 9546618.
In vivo protocol:	1. Veeraveedu PT, Watanabe K, Ma M, Gurusamy N, Palaniyandi SS, Wen J, Prakash P, Wahed MI, Kamal FA, Mito S, Kunisaki M, Kodama M, Aizawa Y. Comparative effects of pranidipine with amlodipine in rats with heart failure. Pharmacology. 2006;77(1):1-10. doi: 10.1159/000091746. Epub 2006 Feb 27. PMID: 16508340. 2. Nakayama N, Ikezono K, Mori T, Yamashita S, Nakayama S, Tanaka Y, Hosokawa T, Minami Y, Masutani K, Yamamura Y, et al. Antihypertensive activity of OPC-13340, a new potent and long-acting dihydropyridine calcium antagonist, in rats. J Cardiovasc Pharmacol. 1990 May;15(5):836-44. doi: 10.1097/00005344-199005000-00021. PMID: 1692946.

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1: Veeraveedu PT, Watanabe K, Ma M, Gurusamy N, Palaniyandi SS, Wen J, Prakash P, Wahed MI, Kamal FA, Mito S, Kunisaki M, Kodama M, Aizawa Y. Comparative effects of pranidipine with amlodipine in rats with heart failure. Pharmacology. 2006;77(1):1-10. Epub 2006 Feb 27. PubMed PMID: 16508340.

2: Murakami M, Mori T, Nakagawasai O, Hagiwara K, Sakurada Y, Mobarakeh II, Murata A, Yamadera F, Miyoshi I, Tan-No K, Yanai K, Tadano T, Iijima T. Inhibitory effect of pranidipine on N-type voltage-dependent Ca2+ channels in mice. Neurosci Lett. 2004 Aug 26;367(1):118-22. PubMed PMID: 15308311.

3: Wahed MI, Watanabe K, Ma M, Nakazawa M, Takahashi T, Hasegawa G, Naito M, Yamamoto T, Kodama M, Aizawa Y. Effects of pranidipine, a novel calcium channel antagonist, on the progression of left ventricular dysfunction and remodeling in rats with heart failure. Pharmacology. 2004 Sep;72(1):26-32. PubMed PMID: 15292652.

4: Mori T, Takase H, Toide K, Hirano T, Kambe T, Nakayama N, Schwartz A. Pranidipine, a 1,4-dihydropyridine calcium channel blocker that enhances nitric oxide-induced vascular relaxation. Cardiovasc Drug Rev. 2001 Spring;19(1):1-8. Review. PubMed PMID: 11314598.

5: Sogabe T, Mori T, Ohura M, Tominaga M, Koga K, Yabuuchi Y. Venodilatory effect of pranidipine, a calcium channel blocker, monitored with perfluorocarbon in vivo (19)F-NMR spectroscopy. Magn Reson Imaging. 2000 Oct;18(8):1011-6. PubMed PMID: 11121706.

6: Takeuchi K, Omura T, Yoshiyama M, Yoshida K, Otsuka R, Shimada Y, Ujino K, Yoshikawa J. Long-acting calcium channel antagonist pranidipine prevents ventricular remodeling after myocardial infarction in rats. Heart Vessels. 1999;14(3):111-9. PubMed PMID: 10776803.

7: Nagahama T, Hayashi K, Fujiwara K, Ozawa Y, Saruta T. Characterization of the renal action of pranidipine in the rat. Arzneimittelforschung. 2000 Mar;50(3):248-53. PubMed PMID: 10758776.

8: Yang J, Fukuo K, Morimoto S, Niinobu T, Suhara T, Ogihara T. Pranidipine enhances the action of nitric oxide released from endothelial cells. Hypertension. 2000 Jan;35(1 Pt 1):82-5. PubMed PMID: 10642279.

9: Hirano T, Mori T, Kido M, Toide K, Ohura M, Fujiki H, Orito K, Yoshida K, Ikezono K, Sumida T, Nakayama N, Yabuuchi Y. Differential properties of the optical-isomers of pranidipine, a 1,4-dihydropyridine calcium channel modulator. Fundam Clin Pharmacol. 1999;13(6):650-5. PubMed PMID: 10626752.

10: Koshita M, Takano H, Nakahira Y, Suzuki H. Pranidipine enhances relaxation produced by endothelium-derived relaxing factor in carotid artery. Eur J Pharmacol. 1999 Dec 3;385(2-3):191-7. PubMed PMID: 10607875.

11: Kim CS, Matsumori A, Goldberg L, Doye AA, McCoy Q, Gwathmey JK. Effects of pranidipine, a calcium channel antagonist, in an avian model of heart failure. Cardiovasc Drugs Ther. 1999 Sep;13(5):455-63. PubMed PMID: 10547227.

12: Tamaki Y, Araie M, Tomita K, Urashima H. Effects of pranidipine, a new calcium antagonist, on circulation in the choroid, retina and optic nerve head. Curr Eye Res. 1999 Sep;19(3):241-7. PubMed PMID: 10487962.

13: Yamada S, Uchida S, Urayama A, Kimura R. In vivo receptor occupancy and plasma concentration of pranidipine, a potent and long-acting dihydropyridine calcium antagonist. Pharmacology. 1999 Oct;59(4):171-82. PubMed PMID: 10474077.

14: Kudo S, Okumura H, Miyamoto G, Ishizaki T. Cytochrome P-450 isoforms involved in carboxylic acid ester cleavage of Hantzsch pyridine ester of pranidipine. Drug Metab Dispos. 1999 Feb;27(2):303-8. PubMed PMID: 9929520.

15: Hashimoto K, Shirafuji T, Sekino H, Matsuoka O, Sekino H, Onnagawa O, Okamoto T, Kudo S, Azuma J. Interaction of citrus juices with pranidipine, a new 1,4-dihydropyridine calcium antagonist, in healthy subjects. Eur J Clin Pharmacol. 1998 Nov-Dec;54(9-10):753-60. PubMed PMID: 9923580.

16: Mori T, Takeuchi T, Ohura M, Miyakoda G, Fujiki H, Orito K, Yoshida K, Hirano T, Yamamura Y, Sumida T, Nakaya Y, Satake H, Hata F. Pranidipine, a new 1,4-dihydropyridine calcium channel blocker, enhances cyclic GMP-independent nitric oxide-induced relaxation of the rat aorta. Mol Cell Biochem. 1998 Jan;178(1-2):335-43. PubMed PMID: 9546618.

17: Hirano T, Ohura M, Orito K, Fujiki H, Miyakoda G, Mori T. Venodilator effects of pranidipine, a 1,4-dihydropyridine Ca2+ channel antagonist, in rats: comparison with nifedipine and amlodipine. Eur J Pharmacol. 1997 Apr 18;324(2-3):201-4. PubMed PMID: 9145772.

18: Rosenthal J, Hittel N, Stumpe KO. Pranidipine, a novel calcium antagonist, once daily, for the treatment of hypertension: a multicenter, double-blind, placebo-controlled dose-finding study. Cardiovasc Drugs Ther. 1996 Mar;10(1):59-66. PubMed PMID: 8723171.

19: Tominaga M, Tsuchihashi T, Kinoshita H, Kobayashi K, Ohya Y, Abe I, Takata Y, Fujishima M. Ambulatory blood pressure monitoring in elderly hypertensives treated with the new calcium antagonist, pranidipine (OPC-13340). Int J Clin Pharmacol Ther. 1995 May;33(5):277-80. PubMed PMID: 7655766.

20: Miyakoda G, Nakayama N, Matsui K, Yabuuchi Y. Mechanisms of the potent and long-lasting antihypertensive action of the new calcium channel blocker pranidipine. Evidence for strong affinity to the calcium channels or membranes. Arzneimittelforschung. 1995 Apr;45(4):471-5. PubMed PMID: 7779144.

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