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Cilnidipine

Cilnidipine structure

CAS No:
132203-70-4
Formula:
C27H28N2O7
Chemical Name:
Cilnidipine
Synonyms:
3,5-Pyridinedicarboxylic acid,1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,3-(2-methoxyethyl) 5-[(2E)-3-phenyl-2-propen-1-yl] ester;3,5-Pyridinedicarboxylic acid,1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,2-methoxyethyl 3-phenyl-2-propenyl ester,(E)-(±)-;3,5-Pyridinedicarboxylic acid,1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,2-methoxyethyl (2E)-3-phenyl-2-propenyl ester;(±)-FRC 8653;FRC 8653;Cilnidipine;Atelec;Cinalong;Siscard;3,5-Pyridinedicarboxylic acid,1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,2-methoxyethyl 3-phenyl-2-propenyl ester,(E)-;FRG 8653;Cinaldipine;Cilacar 10;153220-67-8
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Yellow Crystalline SolidChEBI: A diesterified 1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium channel blocker, it is used as an antihypertensive.Clinidipine is a kind of calcium channel blocker. It is a kind of novel calcium antagonist with the blocking effect on both L-type and N-type calcium channels. It is mainly used for the treatment of hypertension. Based on its effect on both N-type and L-type calcium channel, it can dilate both arterioles and venules, further reducing the pressure

Cilnidipine is a diesterified 1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium channel blocker, it is used as an antihypertensive. It has a role as a calcium channel blocker, an antihypertensive agent and a cardiovascular drug. It is a dihydropyridine, a 2-methoxyethyl ester and a C-nitro compound.|Cilnidipine is a dihydropyridine calcium antagonist. It was jointly developed by Fuji Viscera Pharmaceutical Company, Japan and Ajinomoto, Japan and approved in 1995. Compared with other calcium antagonists, cilnidipine can act on the N-type calcium channel that existing sympathetic nerve end besides acting on L-type calcium channel that similar to most of the calcium antagonists. This drug is approved in China, Japan, Korea, India, and several countries in the European Union.

Cilnidipine Basic Attributes

Molecular Weight：

492.52

Exact Mass：

492.52

EC Number：

1806241-263-5

UNII：

S85436ZG85|4LNU2SU262

DSSTox ID：

DTXSID0046309

ATC Code：

C - Cardiovascular system

HScode：

29333990

Characteristics

PSA：

120

XLogP3：

4.4

Appearance：

light yellow

Density：

1.240±0.06 g/cm3(Predicted)

Melting Point：

115.5-116.6 °C

Boiling Point：

653ºC

Flash Point：

348.5±31.5 °C

Refractive Index：

1.592

Water Solubility：

H2O: Insoluble

Storage Conditions：

Store at +4°C

Vapor Pressure：

0mmHg at 25°C

Toxicity：

LD50 in male, female mice, rats (mg/kg): 5000, 5000, 5000, 4412 orally; 5000 all species s.c.; 1845, 2353, 441, 426 i.p. (Wada)

PKA：

11.39None

Dissociation Constants：

11.39

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

26-39

RTECS Number：

US7975550

Marks：

Precautionary statement(s)：

P280-P305 + P351 + P338

Hazard Statements：

H318

GHS Classification：

|Danger|H318 (97.44%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|P280, P305+P351+P338, and P310|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

The percentage of reports of cilnidipine that express drug toxicity reported as side effects are 5.26%.

Protein Binding：

Cilnidipine presents a very high protein binding that represents to even 98% of the administered dose.

Drug Information

Drug Indication：

Cilnidipine is indicated for the management of hypertension for end-organ protection. It is reported to be useful in elderly patients and in those with diabetes and albuminuria. Cilnidipine has been increasingly used in patients with chronic kidney disease Hypertension is the term used to describe the presence of high blood pressure. The blood pressure is generated by the force of the blood pumped from the heart against the blood vessels. Thus hypertension is caused when there is too much pressure on the blood vessels and this effect can damage the blood vessel.

Pharmacology：

Administration of cilnidipine has been shown to present an antisympathetic profile in vitro and in vivo. It decreases blood pressure safely and effectively without excessive blood pressure reduction or tachycardia.

MeSH：

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Absorption：

Cilnidipine presents a very rapid absorption with a maximum peaked concentration after 2 hours. Its distribution tends to be higher in the liver as well as in kidneys, plasma and other tissues. Cilnidipine does not present a high accumulation in the tissue after repeated oral administration. Cilnidipine is reported to present very low bioavailability determined to be approximately 13%. This low bioavailability is suggested to be due to its low aqueous solubility and high permeability. Hence, efforts have been made in order to find an innovative formulation that can significantly improve the bioavailability of this drug. One of these formulations corresponds to the generation of polymeric nanoparticles which enhance the bioavailability by 2.5-3-fold.|Cilnidipine gets eliminated through the urine in a proportion of 20% of the administered dose and 80% is eliminated by the feces.|Drugs on the group of dihydropyridines such as cilnidipine tend to have a large volume of distribution.

Metabolism/Metabolites：

Cilnidipine is metabolized by both liver and kidney. It is rapidly metabolized by liver microsomes by a dehydrogenation process. The major enzymatic isoform involved in cilnidipine dehydrogenation of the dihydropyridine ring is CYP3A.

Biological Half-Life：

The half-life of the hypotensive effect for cilnidipine is of about 20.4 min.

Mechanism of Action：

Cilnidipine acts on the L-type calcium channels of blood vessels by blocking the incoming calcium and suppressing the contraction of blood vessels, thereby reducing blood pressure. Cilnidipine also works on the N-type calcium channel located at the end of the sympathetic nerve, inhibiting the emission of norepinephrine and suppressing the increase in stress blood pressure.

MeSH Entry Terms：

2-methoxyethyl-3-phenyl-2-propen-1-yl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

Cilnidipine Use and Manufacturing

Methods of Manufacturing

1. In a 250 ml bottle, added material a: 2-(3-nitrophenylmethylene)acetoacetic acid methyl ester (54g, 0.184mol) and material b:3-amino-2-butenoic acid cinnamyl ester (40g, 0.184mol) and anhydrous ethanol (80g), heating reflux 1 hour; 2. To step 1 added concentrated hydrochloric acid to the reaction system (> 35percent) 3.31 ml, continue to reflux for 1 hour, the rear cooling crystallization, filtering to obtain cilnidipine crude; thick quantity : 80.7g; yield 88.98percent ; M.P.: 106.1-106.7 °C; maximum shan Za : 0.2percent, a total of 10 small impurity peak, content: 99.25percent.Receiving product: 80.77gYield 89.07percent, M.P.: 106.0-106.8 °CThe maximum shan Za : 0.29percentA total of 9 small impurity peakContent: 99.18percent 3. In accordance with the weight ratio of ethanol: crude = 3:1 use anhydrous ethanol is added in the amount in step 2 the horizontal thick Sydney obtained in recrystallization, to get finished product Cini the horizontal.Yield 91.5percent, M.P.: 107.4-108.2 °CThe maximum shan Za : 0.1460percentThe minimum shan Za : 0.0502percentA total of 2 a small impurity peakContent: 99.8percent

Uses

antihypertensive;dihydropyridine calcium channel blocker

Computed Properties

Molecular Weight:492.5
XLogP3:4.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:11
Exact Mass:492.18965124
Monoisotopic Mass:492.18965124
Topological Polar Surface Area:120
Heavy Atom Count:36
Complexity:896
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Unspecified

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Cilnidipine
Manufacturer	Zhejiang Jingxin Pharmaceutical Co., Ltd.

Cilnidipine Tablets
Ingredients	Cilnidipine.
Indication	Combined medication: 1. Ephedra It is not recommended for patients to use this product while taking drugs containing ephedra. Ephedrine in ephedra can aggravate the symptoms of hypertension. 2. Hypericum There are no clinical reports of interactions between this product and Hypericum. However, Hypericum has the same metabolic pathway as this product. This product is metabolized by the CYP450 enzyme system, which is a substrate for P-glycoprotein drug transport. Hypericum can activate cytochrome P4503A4 and P-glycoprotein in the human body. In vitro tests have shown that extracts of Hypericum can inhibit cytochrome P450 isoenzymes including P4503A4. Therefore, calcium ion antagonists that can be metabolized by cytochrome P4503A4 should be avoided in combination with Hypericum. 3. Use of this product in combination with other antihypertensive drugs
Specifications	10mg
Manufacturer	Bengbu Fengyuan Pharmaceutical Co., Ltd.

Cilnidipine Soft Capsules
Ingredients	Cilnidipine. Chemical name: 4-methylpyrazine hydrochloride Molecular weight: C8H12N2·HCl·2H2O
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	5mg
Manufacturer	Dalian Making Charm Pharmaceutical Co., Ltd.

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Registered Holders

MANKIND PHARMA LTD

United States
Active
Hunan Jiudian HONGYANG Pharmaceutical Co., Ltd.

China
Active
Yantai Luyin Pharmaceutical Co., Ltd.

China
Active

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