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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/23 02:11:33」(JST)

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Nilvadipine is a calcium channel blocker (CCB) used for the treatment of hypertension and chronic major cerebral artery occlusion.

Pathohistochemical studies have revealed that the volume of the infarction in the middle cerebral artery occlusion model could be decreased by nilvadipine.

Nilvadipine was tested in clinical trial as a possible treatment for Alzheimer's Disease in Ireland by the Roskamp Institute, Florida, USA and Trinity College, Ireland.^[1]

Following this study, an international research consortium led by Trinity College Dublin (Ireland) in May 2011 announced the selection for funding of a large-scale European clinical trial of Nilvadipine, an Alzheimer’s disease drug developed at the Roskamp Institute in Sarasota. More than 500 Alzheimer’s patients will participate in the multicenter Phase III clinical trial designed to study the effectiveness of Nilvadipine.^[2]

Synthesis

Nilvadipine synthesis: Y. Sato, BE 879263; idem, U.S. Patent 4,338,322 (1980, 1982 both to Fujisawa).

The product from the condensation of meta-nitrobenzaldehyde with dimethyl acetal from methyl 4-formylacetoacetate (1) provides the starting material for a dihydropyridine in which one of the methyl groups is replaced with by a nitrile. Rxn of 3 with the enamine from isopropyl acetoacetate (4) affords the corresponding dihydropyridine; hydrolysis of the ketal with aqueous acid affords the aldehyde (5). That function is then converted to the oxime (6) by reaction with hydroxylamine. Treatment of this intermediate with hot acetic acid causes the oxime to dehydrate to a nitrile. There is thus obtained nilvadipine (5).

Notes

See for Flordipine.

References

^ Roskamp Institute | ROSKAMP NILVADIPINE CLINICAL TRIAL Questions and Answers
^ Roskamp Institute | ROSKAMP NILVADIPINE CLINICAL TRIAL Press Release

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

English Journal

Potential for specific dihydropyridine calcium channel blockers to have a positive impact on cognitive function in humans: a systematic review.

Peters J1, Booth A1, Peters R2.
Therapeutic advances in chronic disease.Ther Adv Chronic Dis.2015 Jul;6(4):160-9. doi: 10.1177/2040622315582353.
BACKGROUND: There is some evidence to suggest a possible association between calcium channel blocker (CCB) use and a lower decline in cognitive function compared with use of other hypertensive treatments. In particular, there is an emerging interest in the potential for specific CCBs, particularly t
PMID 26137206

Systematic Review of Randomized Clinical Trials on Safety and Efficacy of Pharmacological and Nonpharmacological Treatments for Retinitis Pigmentosa.

Sacchetti M1, Mantelli F2, Merlo D3, Lambiase A4.
Journal of ophthalmology.J Ophthalmol.2015;2015:737053. Epub 2015 Aug 3.
Aims. Several treatments have been proposed to slow down progression of Retinitis pigmentosa (RP), a hereditary retinal degenerative condition leading to severe visual impairment. The aim of this study is to systematically review data from randomized clinical trials (RCTs) evaluating safety and effi
PMID 26339504

The spleen tyrosine kinase (Syk) regulates Alzheimer amyloid-β production and Tau hyperphosphorylation.

Paris D1, Ait-Ghezala G2, Bachmeier C2, Laco G2, Beaulieu-Abdelahad D2, Lin Y2, Jin C2, Crawford F2, Mullan M2.
The Journal of biological chemistry.J Biol Chem.2014 Dec 5;289(49):33927-44. doi: 10.1074/jbc.M114.608091. Epub 2014 Oct 20.
We have previously shown that the L-type calcium channel (LCC) antagonist nilvadipine reduces brain amyloid-β (Aβ) accumulation by affecting both Aβ production and Aβ clearance across the blood-brain barrier (BBB). Nilvadipine consists of a mixture of two enantiomers, (+)-nilvadipine and (-)-nil
PMID 25331948

Japanese Journal

Histological Protection by Nilvadipine against Neurotoxicity Induced by NOC12, a Nitric Oxide Donor, in the Rat Retina

Biological and Pharmaceutical Bulletin 37(2), 306-310, 2014
NAID 130003390922

Factors Affecting the Absorption of Nilvadipine from Disintegration-Controlled Matrix Tablet in Dogs

Biological and Pharmaceutical Bulletin 34(11), 1731-1736, 2011
NAID 130001252857

Calcium Channel Blocker Nilvadipine, but Not Diltiazem, Inhibits Ocular Inflammation in Endotoxin-Induced Uveitis

Japanese journal of ophthalmology 54(6), 594-601, 2010-11-01
NAID 10027666392

「ニルバジピン」

Nilvadipine
Systematic (IUPAC) name
	5-isopropyl 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Registry Number
ATC code	C08CA10
PubChem	CID: 4494
DrugBank	DB06712
ChemSpider	4338
UNII	0214FUT37J
KEGG	D01908
ChEMBL	CHEMBL517427
Chemical data
Formula	C19H19N3O6
Molecular mass	385.370 g/mol
	SMILES CC1=C(C(C(=C(N1)C#N)C(=O)OC)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OC(C)C ;
	InChI InChI=1S/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3 ; Key:FAIIFDPAEUKBEP-UHFFFAOYSA-N ;
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英: nilvadipine
商: トーワジール、ナフトジール、ニバジール、ニバディップ、ニルジラート、ニルバジピン

[1] Roskamp Institute | ROSKAMP NILVADIPINE CLINICAL TRIAL Questions and Answers

[2] Roskamp Institute | ROSKAMP NILVADIPINE CLINICAL TRIAL Press Release

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nilvadipine