Cilnidipine

Base Information

• Chemical Name: Cilnidipine
• CAS No.: 132203-70-4
• Molecular Formula: C27H28N2O7
• Molecular Weight: 492.529
• Hs Code.: 29333990
• European Community (EC) Number: 634-350-6
• UNII: 97T5AZ1JIP,S85436ZG85,4LNU2SU262
• ChEMBL ID: CHEMBL452076
• DSSTox Substance ID: DTXSID0046309
• Metabolomics Workbench ID: 52049
• NCI Thesaurus Code: C171754
• Nikkaji Number: J326.004F
• Pharos Ligand ID: 1H1BAJBRD5A8
• Wikidata: Q731525
• Wikipedia: Cilnidipine
• Mol file: 132203-70-4.mol

Synonyms:2-methoxyethyl-3-phenyl-2-propen-1-yl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate;cilnidipine;cilnidipine, (+)-isomer;cilnidipine, (-)-isomer;FRC 8653;FRC-8653

Chemical Property of Cilnidipine

Chemical Property:

• Appearance/Colour: yellow crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 97-99 °C
• Refractive Index: 1.581
• Boiling Point: 652.6 °C at 760 mmHg
• PKA: 2.61±0.70(Predicted)
• Flash Point: 348.5 °C
• PSA: 119.68000
• Density: 1.24 g/cm³
• LogP: 5.12780
• Storage Temp.: Store at +4°C
• Solubility.: H2O: ≤2mg/mL
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 492.18965124
• Heavy Atom Count: 36
• Complexity: 896

Purity/Quality:

99% ^*data from raw suppliers

Cilnidipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OCC=CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OCCOC
• Isomeric SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC/C=C/C2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OCCOC
• Recent ClinicalTrials: A Bioequivalence Study Comparing Cilnidipine/Valsartan Combination With Coadministration of Cilnidipine and Valsartan
• Recent NIPH Clinical Trials: Study on Uncontrolled Morning Surge for N-Type CCB and Low-Dose of HCTZ, Using the Internet-through Blood Pressure Data Transmission System
• Description: 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 in the capillary bed. In addition, cilinidipine can attenuate the platelet activation associated with catecholamines. Cilnidipine is a dihydropyridine calcium channel blocker that blocks L- and N-type high-voltage-activated calcium currents in rat hippocampal CA1 pyramidal neurons when used at a concentration of 10 μM. Cilnidipine (3 mg/kg) reduces the pressor response to acute cold stress, as well as mean blood pressure, in spontaneously hypertensive rats. It dose-dependently reduces mean blood pressure and cerebral vascular resistance without affecting cerebral blood flow in anesthetized rats at doses ranging from 3-100 μg/kg. Cilnidipine (100 μg/kg, i.p.) reduces cerebral infarction area in a rat model of focal brain ischemia. Cilnidipine is a dihydropyridine calcium antagonist introduced for the treatment of essential and severe hypertension and hypertension associated with renopathy. Cilnidipine has been demonstrated to exert a potent vasodilating effect by blocking calcium influx via dihydropyridine-sensitive, voltage-dependent calcium channels. Compared to nifedipine and nicardipine, cilnidipine is superior, especially for long-term treatment, due to its characteristics of slow onset and long duration with less cardiodepressant activity. Cilnidipine is reportedly well tolerated with low toxicity. It may also be useful in ischemic heart disease.
• Uses: A dihydropyridine calcium channel blocker. A dihydropyridine calcium channel blocker antihypertensive;dihydropyridine calcium channel blocker Cilnidipine has been used:in cell viability assay of pheochromocytoma (nPC12) cellsin photoirradiation and photodegradation studies to understand effect on albuminuria in diabetic nephropathy

Technology Process of Cilnidipine

There total 3 articles about Cilnidipine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.5%

3-amino-2-butenoic acid cinnamyl ester (103909-86-0,113898-97-8) + (E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate (39562-22-6) → cilnidipine (132203-70-4)

Guidance literature:

3-amino-2-butenoic acid cinnamyl ester; (E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate; In ethanol; for 1h; Reflux;

With hydrogenchloride; In ethanol; water; for 1h; Solvent; Reagent/catalyst; Reflux;

Reference yield: 91.4%

3-amino-2-butenoic acid cinnamyl ester (103909-86-0,113898-97-8) + C14H17NO6 → cilnidipine (132203-70-4)

Guidance literature:

In ethanol; at 50 ℃; Solvent; Temperature;

Reference yield:

→ cilnidipine (132203-70-4)

Guidance literature:

upstream raw materials:

3-amino-2-butenoic acid cinnamyl ester

(E/Z)-2-methoxyethyl 2-(3-nitrobenzylidene)-acetoacetate

Downstream raw materials:

3-cinnamyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

(2E)-3-phenyl-2-propen-1-ol

Refernces

• 1、 -. "Preparation method of cilnidipine". Paragraph 0029-0045. . Retrieved 2020/05/08.
• 2、 -. "Antihypertensive 1,4-dihydropyridines having a conjugated ester". . . Retrieved 2008/06/13.