PRANIDIPINE

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

Structure Search

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+

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800000287 | https://www.ncbi.nlm.nih.gov/pubmed/9546618 | https://www.ncbi.nlm.nih.gov/pubmed/10487962 | https://www.ncbi.nlm.nih.gov/pubmed/10547227 | https://www.ncbi.nlm.nih.gov/pubmed/10607875

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

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel alpha-1C subunit 44 Target ID: CHEMBL1940 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20382537	Antagonist 2849		37.0 nM [IC50]

PubMed

Title	Date	PubMed
Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions.	2012-07	22039822
Quantitative structure-interaction relationship analysis of 1,4-dihydropyridine drugs in concomitant administration with grapefruit juice.	2012-03	22530299
Relationship between lipophilicities of 1,4-dihydropyridine derivatives and pharmacokinetic interaction strengths with grapefruit juice.	2008-01	18176062
The effects of calcium channel blockers are not related to their chemical structure in the collar model of the rabbit.	2007-04-06	17408056
Comparative effects of pranidipine with amlodipine in rats with heart failure.	2006	16508340
Effects of pranidipine, a novel calcium channel antagonist, on the progression of left ventricular dysfunction and remodeling in rats with heart failure.	2004-09	15292652
Inhibitory effect of pranidipine on N-type voltage-dependent Ca2+ channels in mice.	2004-08-26	15308311
Effects of lomerizine, a novel Ca2+ channel blocker, on the normal and endothelin-1-disturbed circulation in the optic nerve head of rabbits.	2001-04	11324981
Pranidipine, a 1,4-dihydropyridine calcium channel blocker that enhances nitric oxide-induced vascular relaxation.	2001	11314598
Effects of long-term treatment with calcium antagonists on periarterial nerve function in the mesenteric artery of spontaneously hypertensive rats.	2000-10	11128038
Venodilatory effect of pranidipine, a calcium channel blocker, monitored with perfluorocarbon in vivo (19)F-NMR spectroscopy.	2000-10	11121706
Characterization of the renal action of pranidipine in the rat.	2000-03	10758776
Pranidipine enhances the action of nitric oxide released from endothelial cells.	2000-01	10642279
Role of protein kinase C in angiotensin II-induced constriction of renal microvessels.	2000-01	10620202
Pranidipine enhances relaxation produced by endothelium-derived relaxing factor in carotid artery.	1999-12-03	10607875
[In vivo measurement of ocular circulation with the laser speckle method--development of apparatus and application in ophthalmological research].	1999-12	10643292
Effects of pranidipine, a calcium channel antagonist, in an avian model of heart failure.	1999-09	10547227
Effects of pranidipine, a new calcium antagonist, on circulation in the choroid, retina and optic nerve head.	1999-09	10487962
Long-acting calcium channel antagonist pranidipine prevents ventricular remodeling after myocardial infarction in rats.	1999	10776803
Differential properties of the optical-isomers of pranidipine, a 1,4-dihydropyridine calcium channel modulator.	1999	10626752
Cardiovascular effects of OPC-13340, a potent, long-acting 1,4-dihydropyridine calcium channel blocker, in dogs.	1993-01-01	8323415

Patents

Name

Type

Language

ACALAS

Preferred Name

English

PRANIDIPINE

Official Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, METHYL 3-PHENYL-2-PROPENYL ESTER, (E)-

Common Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, METHYL (2E)-3-PHENYL-2-PROPENYL ESTER

Common Name

English

FRC-8411

Code

English

(E)-CINNAMYL METHYL (±)-1,4-DIHYDRO-2,6-DIMETHYL-4-(M-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLATE

Systematic Name

English

3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-METHYL 5-((2E)-3-PHENYL-2-PROPEN-1-YL) ESTER

Systematic Name

English

PRANIDIPINE [JAN]

Common Name

English

pranidipine [INN]

Common Name

English

OPC-13340

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C333