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Azelnidipine

Product Name
Azelnidipine
CAS No.
123524-52-7
Chemical Name
Azelnidipine
Synonyms
CS-905;CS-499;RS-9054;Calblock;Azelpine;Azedipine;Azelidipine;Azenildipine;AZELNIDIPINE;AZELINIDIPINE
CBNumber
CB1781980
Molecular Formula
C33H34N4O6
Formula Weight
582.65
MOL File
123524-52-7.mol
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Azelnidipine Property

Melting point:
120-126°C
Boiling point:
709.3±60.0 °C(Predicted)
Density 
1.33±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
DMSO: >10mg/mL
pka
7.89(at 25℃)
form 
powder
color 
Yellow
Merck 
14,907
InChIKey
ZKFQEACEUNWPMT-UHFFFAOYSA-N
CAS DataBase Reference
123524-52-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-41
Safety Statements 
26-39
WGK Germany 
3
RTECS 
US7968332
HS Code 
2933.79.1500
Toxicity
LD50 in female, male mice, female, male rats (mg/kg): 785, 979, 1267, 1971 orally
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A7106
Product name
Azelnidipine
Purity
≥98% (HPLC), powder
Packaging
10mg
Price
$163
Updated
2024/03/01
Sigma-Aldrich
Product number
A7106
Product name
Azelnidipine
Purity
≥98% (HPLC), powder
Packaging
50mg
Price
$736
Updated
2024/03/01
TCI Chemical
Product number
A2433
Product name
Azelnidipine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$87
Updated
2024/03/01
TCI Chemical
Product number
A2433
Product name
Azelnidipine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$299
Updated
2024/03/01
Cayman Chemical
Product number
21249
Product name
Azelnidipine
Purity
≥98%
Packaging
500mg
Price
$57
Updated
2024/03/01
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Azelnidipine Chemical Properties,Usage,Production

Description

Azelnidipine, a member of the 1,4-dihydropyridine class of L-type calcium channel blockers with a slow onset profile, was marketed in Japan for the treatment of hypertension. Azelnidipine is synthesized via the condensation of iso-propyl 2-(3- nitrobenzylidene)acetoacetate with (1-diphenylmethylazetidin-3-yl)-3,3-diamino acrylate. The diamino acrylate intermediate is prepared from the cyanoacetic ester by sequential treatment with HCl and ammonia. In receptor binding studies using porcine heart membrane fractions, azelnidipine exhibits an IC50 of 3.1 nM and an apparent Ki of 2.1 nM. Its tight binding and slow onset are correlated with its high lipophilicity. A slow onset is also noted in vitro in a rat aortic strip contraction assay, and this effect continues after removal of the drug from the bath solution. In the conscious spontaneously hypertensive rat (SHR) model of hypertension, it was more potent that nicardipine and also had a more gradual onset and long-lasting effect. This effect was noted both when dosed orally or intravenously. When SHR dosed at 1 or 3 mpk/day for 15 weeks, a sustained reduction in systolic blood pressure was noted (19 and 43 mmHg reduction, respectively). Cardiac output was increased and total peripheral resistance was decreased in each group. Clinical studies of patients with mild-to-moderate hypertension have shown that long-term treatment with azelnidipine provided a sustained decrease in blood pressure (mean reduction systolic /diastolic: 27.8/16.6 mmHg). It similarly controlled blood pressure, as did amlodipine at 24 h. It possesses a gradual onset of activity with plasma levels increasing before the antihypotensive effect is attained. After plasma levels drop, the pharmacodynamic effect is sustained. In clinical studies, azelnidipine did not show reflex tachycardia, a common side effect of this class. Most common side effects were facial flushing and headache, similar to other dihydropyridines. Azelnidipine is dosed orally once daily (8–16 mg), is rapidly absorbed in a dose-dependent fashion, and has a mean terminal half-life of 19.2 h (8 mg dosage p.o. for seven days). Uniquely, it possesses a 2-amino function associated with a longer half-life than related agents wherein this moiety is a methyl. The very highly lipophilic 3-carboxylic ester side-chain is purported to contribute to the gradual onset of activity and prolonged pharmacodynamic effect, unlike other drugs in this class. This compound exhibits a much less pronounced first-pass metabolic effect than nicardipine.

Chemical Properties

Yellow Solid

Originator

Sankyo (Japan)

Uses

Azelnidipine is a dihydropyridine calcium channel blocker with antihypertensice activity. Azelnidipine is used for treating ischemic heart disease and cardiac remodeling after myocardial infarction. S tudies show that Azelnidipine ttreatment can reduce the risk of hyperglycemia induced metabolic disorders

Definition

ChEBI: Azelnidipine is an isopropyl ester.

Application

Azelnidipine is a novel dihydropyridine derivative, a L-type calcium channel blocker, and an antihypertensive. Acute administration of azelnidipine prevents a sudden drop of cardiac function after acute stress. Azelnidipine may have a protective role in inflammation associated with atherosclerosis.

brand name

Calblock

Biological Activity

Azelnidipine, a novel dihydropyridine derivative, is a L-type calcium channel blocker and antihypertensive. Unlike other L-type calcium channel blockers, azelnidipine causes minimal stimulation of the sympathetic nervous system despite its significant depressor effect. Azelnidipine may have a protective role in inflammation in atherosclerosis.

Synthesis

A solution of benzhydrylamine (46) and epichlorohydrin (47) was mixed without adding solvent to give azetidinol 48 in 57% yield. DCC coupling between cyanoacetic acid (49) and azetidinol 48 in hot THF gave ester 50 in 93% yield. Cyanoester 50 was treated with ethanol and HCl gas in chloroform to give imidate HCl salt 51, which was treated with ammonia gas in chloroform and ammonium acetate in acetonitrile to give the corresponding amidinoacetate 52. A modified Hantzsch reaction was employed to construct the 2-amino-1,4- dihydropyridine core structure. Compound 52 was condensed with 2-(3-nitrobenzylidene)acetic acid isopropyl ester (55) in the presence of NaOMe in refluxing isopropanol to give the cyclized product, azelnidipine (V) in 74% yield. Benzylideneacetoacetate 55 was obtained through the Knoevenagel reaction employing 3-nitrobenzaldehyde (53) and isopropyl acetoacetate (54) in isopropanol containing a catalytic amount of piperidinium acetate at 45-55oC in 65% yield.

Azelnidipine Preparation Products And Raw materials

Raw materials

Preparation Products

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Azelnidipine Suppliers

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View Lastest Price from Azelnidipine manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Azelnidipine 123524-52-7
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2024-10-31
Henan Bao Enluo International TradeCo.，LTD
Product
Azelnidipine 123524-52-7
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-08-02
Hebei Mujin Biotechnology Co.,Ltd
Product
Azelnidipine 123524-52-7
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-28

123524-52-7, AzelnidipineRelated Search:

Thiophanate-methyl Nimodipine Methyl salicylate Nifedipine Tribenuron methyl Amlodipine Kresoxim-methyl Glycine METSULFURON METHYL 6-Aminocaproic acid Orlistat Palonosetron Hydrochloride Olanzapine Methyl Methyl bromide 1-Diphenylmethylazetidine 1-Benzylazetidin-3-ol 1-benzhydrylazetidin-3-Ol

  • AZELNIDIPINE
  • 3-[1-(Diphenylmethyl)-3-azetidinyl]-5-(1-methylethyl-2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
  • AzelnidipineC33H34N406
  • AZELINIDIPINE
  • AZELNIDIPINE(FORR&DONLY)
  • CS-905, RS-9054, 2-Amino-1,4-dihydro-6-methyl-4-(3 nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) ester
  • Azelidipine
  • Azenildipine
  • Calblock
  • CS-905
  • 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(methylethyl) ester
  • (±)-2-AMino-1,4-dihydro-6-Methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-[1-(DiphenylMethyl)-3-azetidinyl] 5-(1-Methylethyl) Ester
  • Calblock 3-[1-(DiphenylMethyl)-3-azetidinyl] 5-isopropyl (±)-2-AMino-1,4-dihyd
  • Azelnidipine (Crystalline forM α)
  • 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-aMino-6-Methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  • Azelnidipine, >=99%
  • 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-
  • Azelnidipine USP/EP
  • 3,5-Pyridinedicarboxylic acid, 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) ester
  • Azelnidipine 2-Amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(methylethyl) ester
  • RS-9054
  • 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridi
  • 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid O3-[1-(diphenylmethyl)-3-azetidinyl] ester O5-propan-2-yl ester
  • CS-499
  • Azelnidipine Azelnidipine
  • Azelnidipine &gt
  • 2-Amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-[1-(Diphenylmethyl)-3-azetidinyl] 5-Isopropyl Ester
  • 3-[1-(Diphenylmethyl)-3-azetidinyl] 5-Isopropyl 2-Amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
  • Azelnidipine USP/EP/BP
  • Azelnidipine (UR12592, CS-905, CCRIS-8650)
  • AzelnidipineQ: What is Azelnidipine Q: What is the CAS Number of Azelnidipine Q: What is the storage condition of Azelnidipine Q: What are the applications of Azelnidipine
  • Fold the horizon
  • Azedipine
  • Azelnidipine Reference Standard
  • Azelnidipine, ≥ 98.0%
  • Azelnidipine powder
  • Azelpine
  • 123524-52-7
  • 23524-52-7
  • C33H34N4O6
  • Inhibitors
  • Cardiovascular Drugs
  • API