105979-17-7

Basic information

• Product Name: Benidipine
• Synonyms: (R*,R*)-(±)-(3,5-Pyridinedicarboxylic acid 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-methyl 1- (phenylmethyl)-3-piperidinyl ester monohydrochloride;3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-diMethyl-4-(3-nitrophenyl)-, 3-Methyl5-[(3R)-1-(phenylMethyl)-3-piperidinyl] ester, (4R)-rel-;NACADIPINE;BENIDIPINE;BENIDIPINE HCL;CAPADIPINE;CONIEL;KW-3049
• CAS NO: 105979-17-7
• Molecular Formula: C₂₈H₃₁N₃O₆
• Molecular Weight: 505.57
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 105979-17-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 625.2 °C at 760 mmHg
• Flash Point: 331.9 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 1.5E-15mmHg at 25°C
• Refractive Index: 1.621
• PKA: pKa 7.34(H2O(long extrapolation) ) (Uncertain)
• Water Solubility: 316μg/L at 25℃
• CAS DataBase Reference: Benidipine(CAS DataBase Reference)
• NIST Chemistry Reference: Benidipine(105979-17-7)
• EPA Substance Registry System: Benidipine(105979-17-7)

Safety Data

• Hazardous Substances Data: 105979-17-7(Hazardous Substances Data)

Usage

Uses

Benidipine (CAS# 105979-17-7) is a 1,4-dihydropyridine and a calcium channel antagonist. Antihypertensive.

Enzyme inhibitor

This oral, once-daily antihypertensive agent (FW = 505.57 g/mol; CAS 105979-17-7), also known by its code name KW-3049, trade name Coniel?, and systematic name O -methyl,O -[(3R)-1-(phenylmethyl)piperidin-3-yl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, is a dihydropyridine-class calcium ion blocker that is effective against L-, N-, and T-channels, with potent and selective inhibitory action on cardiac slow calcium channels. Benidipine bound stereospecifically to nitrendipine binding sites of rat myocardium with high affinity (Ki = 0.13 nM) and to the rat brain a1-adrenergic receptor (Ki = 1.2 μM). KW-3049 exhibited no remarkable binding affinity to a2 adrenergic, b-adrenergic, D2 dopamine, H1 histamine, S2 serotonin, A1 adenosine, A2 adenosine and muscarinic cholinergic receptors at 100 μM.

InChI:InChI=1/C28H31N3O6/c1-18-24(27(32)36-3)26(21-11-7-12-22(15-21)31(34)35)25(19(2)29-18)28(33)37-23-13-8-14-30(17-23)16-20-9-5-4-6-10-20/h4-7,9-12,15,23,26,29H,8,13-14,16-17H2,1-3H3/t23-,26-/m1/s1

Upstream product

• 76093-32-8 (4S)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid 
• 76093-31-7 1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid 
• 76093-34-0 (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 62414-68-0 (3R)-piperidin-3-ol 
• 6859-99-0 3-hydroxypiperazine 
• 88712-56-5 methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate 
• 91599-81-4 (R)-N-benzyl-3-hydroxypiperidine 

Related news

The L-, N-, and T-type triple calcium channel blocker Benidipine (cas 105979-17-7) acts as an antagonist of mineralocorticoid receptor, a member of nuclear receptor family07/28/2019

Aldosterone-induced activation of mineralocorticoid receptor, a member of the nuclear receptor family, results in increased tissue damage such as vascular inflammation and cardiac and perivascular fibrosis. Benidipine, a long-lasting dihydropyridine calcium channel blocker, is used for hypertens...detailed

The effect of hypertension, aging and Benidipine (cas 105979-17-7) on arterial elasticity in elderly hypertensives07/26/2019

SummaryFour hundred and 16 subjects (average age, 56.2 years; range, 20–92 years; Men/Women, 207/209) undergoing annual health check-up were studied for the effect of aging and hypertension on arterial compliance or elasticity index, which were measured after a 10 min rest in the supine positio...detailed

Determination of Benidipine (cas 105979-17-7) in human plasma using liquid chromatography–tandem mass spectrometry07/25/2019

We developed a method for determining benidipine, a dihydropyridine analogue calcium-channel blocker, in plasma using liquid chromatography–tandem mass spectrometry (LC–MS–MS). Benidipine and benidipine-d5, an internal standard, were extracted from plasma using diethyl ether in the presence o...detailed

Effect of Benidipine (cas 105979-17-7) in Human Internal Mammary Artery and Clinical Implications07/24/2019

BackgroundGraft spasm remains challenging in coronary artery bypass grafting (CABG). Calcium antagonists are commonly used in patients with coronary artery disease. This study investigated the inhibitory effect of third-generation dihydropyridine calcium channel antagonist benidipine on the vaso...detailed

Computer-guided drug repurposing: Identification of trypanocidal activity of clofazimine, Benidipine (cas 105979-17-7) and saquinavir07/23/2019

In spite of remarkable advances in the knowledge on Trypanosoma cruzi biology, no medications to treat Chagas disease have been approved in the last 40 years and almost 8 million people remain infected. Since the public sector and non-profit organizations play a significant role in the research ...detailed

Prevention of infertility induced by ovarian ischemia reperfusion injury by Benidipine (cas 105979-17-7) in rats: Biochemical, gene expression, histopathological and immunohistochemical evaluation07/22/2019

IntroductionBenidipine has been reported to prevent the ischemia/reperfusion (I/R) damage in heart tissue and to suppress oxidant and proinflammatory cytokine production, increased by I/R. However, There was no information about the effects of benidipine on I/R injury in the ovary and the damage...detailed

Relevant articles and documents

THERAPY FOR COMPLICATIONS OF DIABETES

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

Synthesis and pharmacological activity of stereoisomers of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester

1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester 1, a highly potent calcium antagonist, was separated into stereo- and optical isomers to investigate the differences of antihypertensive activities between them. Fractional crystallization of the hydrochlorides of 1 gave α- and β-diasterioisomers. The α-isomer (benidipine hydrochloride, KW-3049) showed very strong hypotensive effect, but little activity was observed in the β-isomer. From optically resolved 1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridi necarboxylic acids 2, and 1-benzyl-3-piperidinols 3, four optical isomers of 1 were synthesized, and their absolute configurations were deduced. The hypotensive activity of (+)-α, namely (S)-(S)-1, was 30 to 100 times stronger than that of (-)-α in intravenously administered spontaneously hypertensive rats.