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MedKoo Cat#: 319565 | Name: Pranidipine
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Description:

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

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
Pranidipine
CAS#99522-79-9

Theoretical Analysis

MedKoo Cat#: 319565

Name: Pranidipine

CAS#: 99522-79-9

Chemical Formula: C25H24N2O6

Exact Mass: 448.1634

Molecular Weight: 448.48

Elemental Analysis: C, 66.95; H, 5.39; N, 6.25; O, 21.40

Price and Availability

Size Price Availability Quantity
10mg USD 295.00
50mg USD 1,050.00
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Related CAS #
No Data
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
View handling instruction
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/
Solvent mg/mL mM comments
Solubility
DMSO 180.0 401.36
Ethanol 2.0 4.46
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 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.

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. 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.
1: Uesawa Y, Mohri K. Quantitative structure-interaction relationship analysis of 1,4-dihydropyridine drugs in concomitant administration with grapefruit juice. Pharmazie. 2012 Mar;67(3):195-201. PMID: 22530299. 2: Uesawa Y, Takeuchi T, Mohri K. Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. doi: 10.2174/138920112800958878. PMID: 22039822. 3: Uesawa Y, Mohri K. Relationship between lipophilicities of 1,4-dihydropyridine derivatives and pharmacokinetic interaction strengths with grapefruit juice. Yakugaku Zasshi. 2008 Jan;128(1):117-22. doi: 10.1248/yakushi.128.117. PMID: 18176062. 4: Yasa M, Kerry Z, Reel B, Yetik Anacak G, Ertuna E, Ozer A. The effects of calcium channel blockers are not related to their chemical structure in the collar model of the rabbit. J Int Med Res. 2007 Jan-Feb;35(1):59-71. doi: 10.1177/147323000703500106. PMID: 17408056. 5: 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. 6: 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. doi: 10.1016/j.neulet.2004.05.092. PMID: 15308311. 7: 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. doi: 10.1159/000078629. PMID: 15292652. 8: Toriu N, Sasaoka M, Shimazawa M, Sugiyama T, Hara H. Effects of lomerizine, a novel Ca2+ channel blocker, on the normal and endothelin-1-disturbed circulation in the optic nerve head of rabbits. J Ocul Pharmacol Ther. 2001 Apr;17(2):131-49. doi: 10.1089/10807680151125456. PMID: 11324981. 9: 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. doi: 10.1111/j.1527-3466.2001.tb00179.x. PMID: 11314598. 10: Nakatsuma A, Kawasaki H, Kurosaki Y, Futagami K, Araki H, Gomita Y. Effects of long-term treatment with calcium antagonists on periarterial nerve function in the mesenteric artery of spontaneously hypertensive rats. Jpn J Pharmacol. 2000 Oct;84(2):156-62. doi: 10.1254/jjp.84.156. PMID: 11128038. 11: 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. doi: 10.1016/s0730-725x(00)00194-6. PMID: 11121706. 12: 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. doi: 10.1007/BF02482294. PMID: 10776803. 13: 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. doi: 10.1055/s-0031-1300194. PMID: 10758776. 14: Araie M. [In vivo measurement of ocular circulation with the laser speckle method--development of apparatus and application in ophthalmological research]. Nippon Ganka Gakkai Zasshi. 1999 Dec;103(12):871-909. Japanese. PMID: 10643292. 15: 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. doi: 10.1161/01.hyp.35.1.82. PMID: 10642279. 16: 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. doi: 10.1111/j.1472-8206.1999.tb00376.x. PMID: 10626752. 17: Nagahama T, Hayashi K, Ozawa Y, Takenaka T, Saruta T. Role of protein kinase C in angiotensin II-induced constriction of renal microvessels. Kidney Int. 2000 Jan;57(1):215-23. doi: 10.1046/j.1523-1755.2000.00822.x. PMID: 10620202. 18: 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. 19: 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. doi: 10.1023/a:1007816309841. PMID: 10547227. 20: 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. doi: 10.1076/ceyr.19.3.241.5318. PMID: 10487962.