Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C25H24N2O6 |
| Molecular Weight | 448.4679 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C1=C(C)NC(C)=C(C1C2=CC(=CC=C2)[N+]([O-])=O)C(=O)OC\C=C\C3=CC=CC=C3
InChI
InChIKey=XTFPDGZNWTZCMF-DHZHZOJOSA-N
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+
Pranidipine is the calcium channel blocker. Pranidipine did not affect the sensitivity of the contractile proteins to calcium. Pranidipine also did not alter cyclic GMP-induced relaxation in alpha-toxin-skinned vascular preparations. Pranidipine also prolonged glyceryl trinitrate-induced relaxation in the endothelium denuded rat aorta. Pranidipine enhances cyclic GMP-independent NO-induced relaxation of smooth muscle by a mechanism other than through NO-induced hyperpolarization. These effects were in direct contrast to amlodipine, another new 1,4-dihydropyridine calcium antagonist. Pranidipine increased blood velocity and probably blood flow in the optic nerve head, choroid, and retina of rabbits. Pranidipine was not detrimental to global cardiac function in animals with dilated cardiomyopathy. Pranidipine enhances relaxation produced by endothelium-derived relaxing factor in carotid artery. Pranidipine was investigated as pharmacological agent for the treatment of angina pectoris and hypertension.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Long-acting calcium channel antagonist pranidipine prevents ventricular remodeling after myocardial infarction in rats. | 1999 |
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| Differential properties of the optical-isomers of pranidipine, a 1,4-dihydropyridine calcium channel modulator. | 1999 |
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| [In vivo measurement of ocular circulation with the laser speckle method--development of apparatus and application in ophthalmological research]. | 1999 Dec |
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| Pranidipine enhances relaxation produced by endothelium-derived relaxing factor in carotid artery. | 1999 Dec 3 |
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| Effects of pranidipine, a new calcium antagonist, on circulation in the choroid, retina and optic nerve head. | 1999 Sep |
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| Pranidipine enhances the action of nitric oxide released from endothelial cells. | 2000 Jan |
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| Role of protein kinase C in angiotensin II-induced constriction of renal microvessels. | 2000 Jan |
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| Characterization of the renal action of pranidipine in the rat. | 2000 Mar |
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| Effects of long-term treatment with calcium antagonists on periarterial nerve function in the mesenteric artery of spontaneously hypertensive rats. | 2000 Oct |
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| Venodilatory effect of pranidipine, a calcium channel blocker, monitored with perfluorocarbon in vivo (19)F-NMR spectroscopy. | 2000 Oct |
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| Effects of lomerizine, a novel Ca2+ channel blocker, on the normal and endothelin-1-disturbed circulation in the optic nerve head of rabbits. | 2001 Apr |
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| Pranidipine, a 1,4-dihydropyridine calcium channel blocker that enhances nitric oxide-induced vascular relaxation. | 2001 Spring |
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| Inhibitory effect of pranidipine on N-type voltage-dependent Ca2+ channels in mice. | 2004 Aug 26 |
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| Effects of pranidipine, a novel calcium channel antagonist, on the progression of left ventricular dysfunction and remodeling in rats with heart failure. | 2004 Sep |
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| Comparative effects of pranidipine with amlodipine in rats with heart failure. | 2006 |
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| The effects of calcium channel blockers are not related to their chemical structure in the collar model of the rabbit. | 2007 Jan-Feb |
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| Relationship between lipophilicities of 1,4-dihydropyridine derivatives and pharmacokinetic interaction strengths with grapefruit juice. | 2008 Jan |
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| Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. | 2012 Jul |
|
| Quantitative structure-interaction relationship analysis of 1,4-dihydropyridine drugs in concomitant administration with grapefruit juice. | 2012 Mar |
Patents
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C333
Created by
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| Code System | Code | Type | Description | ||
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100000081397
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PRANIDIPINE
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DTXSID00875518
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9DES9QVH58
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CHEMBL1096842
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C73027
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SUB09997MIG
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99522-79-9
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6846
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6436048
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C048161
Created by
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ACTIVE MOIETY
