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

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

Used in Pharmaceutical Industry:
Benidipine is used as an antihypertensive agent for the treatment of high blood pressure (hypertension). It helps to lower blood pressure by dilating blood vessels, which in turn reduces the resistance against the flow of blood, allowing the heart to pump more efficiently and with less strain.
Additionally, Benidipine may also be used in other cardiovascular applications due to its effects on calcium channels, which can have implications for conditions such as angina (chest pain) and certain types of arrhythmias (irregular heartbeats). However, the primary application of Benidipine remains its use as an antihypertensive medication.

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

• 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 
• 6859-99-0 3-hydroxypiperazine 
• 62414-68-0 (3R)-piperidin-3-ol 
• 76093-34-0 (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid 
• 76093-31-7 1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid 
• 76093-32-8 (4S)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid 

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.

ANTIHYPERTENSIVE THERAPY

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

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.