Azelnidipine

Names

[ Name ]:
Azelnidipine

[Synonym ]:
Azelnidipine
3-[1-(Diphenylmethyl)-3-azetidinyl] 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate
3-[1-(Diphenylmethyl)azetidin-3-yl] 5-isopropyl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
UNII:PV23P19YUG
3,5-Pyridinedicarboxylic acid (2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)
3-[1-(diphenylmethyl)azetidin-3-yl] 5-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
3-O-(1-benzhydrylazetidin-3-yl) 5-O-propan-2-yl 2-amino-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
(±)-1,4-Dihydro-2-amino-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-(1-(Diphenylmethyl)-3-azetidinyl) 5-(1-Methylethyl) Ester
3,5-Pyridinedicarboxylic acid, 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-, 3-[1-(diphenylmethyl)-3-azetidinyl] 5-(1-methylethyl) ester
3-(1-(Diphenylmethyl)-3-azetidinyl) 5-Isopropyl (±)-2-Amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate
MFCD00865803

Biological Activity

[Description]:

Azelnidipine(CS 905; Calblock) is a novel dihydropyridine derivative, a L-type calcium channel blocker, and an antihypertensive.IC50 value:Target: L-type calcium channelAcute administration of azelnidipine prevents a sudden drop of cardiac function after acute stress. Azelnidipine may have a protective role in inflammation associated with atherosclerosis.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Cardiovascular Disease

[References]

[1]. Komoda H, Inoue T, Node K. Anti-inflammatory properties of azelnidipine, a dihydropyridine-based calcium channel blocker. Clin Exp Hypertens. 2010 Jan;32(2):121-8.

[2]. Kain V, Kumar S, Sitasawad SL. Azelnidipine prevents cardiac dysfunction in streptozotocin-diabetic rats by reducing intracellular calcium accumulation, oxidative stress and apoptosis. Cardiovasc Diabetol. 2011 Nov 4;10:97.

[3]. Takano Y, Ueyama T, Ishikura F. Azelnidipine, unique calcium channel blocker could prevent stress-induced cardiac dysfunction like α·β blocker. J Cardiol. 2012 Jul;60(1):18-22.

[4]. Shimizu T, Tanaka T, Iso T et al. Azelnidipine inhibits MSX2-dependent osteogenic differentiation and matrix mineralization of vascular smooth muscle cells. Int Heart J. 2012;53(5):331-5.

[5]. Ohyama T, Sato K, Kishimoto K et al. Azelnidipine is a calcium blocker that attenuates liver fibrosis and may increase antioxidant defence. Br J Pharmacol. 2012 Feb;165(4b):1173-87.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
709.3±60.0 °C at 760 mmHg

[ Melting Point ]:
120-126ºC

[ Molecular Formula ]:
C₃₃H₃₄N₄O₆

[ Molecular Weight ]:
582.646

[ Flash Point ]:
382.8±32.9 °C

[ Exact Mass ]:
582.247864

[ PSA ]:
139.71000

[ LogP ]:
4.21

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.659

[ Storage condition ]:
Room temp

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: US7968332

CHEMICAL NAME :: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2-amino-6-methyl-4-(3-nitrophenyl)-, 3-(1-(diphenylmethyl)-3-azetidinyl)-5-(1-methylethyl) esster, (+-)-

CAS REGISTRY NUMBER :: 123524-52-7

LAST UPDATED :: 199803

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C33-H34-N4-O6

MOLECULAR WEIGHT :: 582.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3640 mg/kg/1Y-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - urine volume increased Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - changes in chlorine

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25,1757,1997

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H318

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
26-39

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
US7968332

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Anti-atherogenic effects of the combination therapy with olmesartan and azelnidipine in diabetic apolipoprotein E-deficient mice.

Tohoku J. Exp. Med. 228 , 305-315, (2012)

Many studies have aimed to identify anti-atherogenic agents in cardiovascular medicine. We have recently demonstrated that the combination therapy with olmesartan (OLM), an angiotensin II receptor blo...

The pharmacological differences in antianginal effects of long-lasting calcium channel blockers: azelnidipine and amlodipine.

J. Cardiovasc. Pharmacol. 61(1) , 63-9, (2013)

We examined antianginal effects of azelnidipine and amlodipine in an arginine vasopressin-induced rat anginal model. Oral administration of azelnidipine or amlodipine produced long lasting inhibition ...

Azelnidipine prevents cardiac dysfunction in streptozotocin-diabetic rats by reducing intracellular calcium accumulation, oxidative stress and apoptosis.

Cardiovasc. Diabetol. 10 , 97, (2011)

Numerous evidences suggest that diabetic heart is characterized by compromised ventricular contraction and prolonged relaxation attributable to multiple causative factors including calcium accumulatio...

Related Compounds

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