3-(2-methoxyethyl) 5-(3-phenylprop-2-en-1-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 72614
• Molecular Formular: C27H28N2O7
• Molecular Mass: 492.52042
• Monoisotopic Mass: 492.18965125
• SMILES: c1ccc(cc1C1C(=C(NC(=C1C(=O)OCCOC)C)C)C(=O)OC/C=C/c1ccccc1)[N+](=O)[O-]
• Canonical SMILES: COCCOC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC/C=C/c1ccccc1)C
• InChI: InChI=1S/C27H28N2O7/c1-18-23(26(30)35-14-8-11-20-9-5-4-6-10-20)25(21-12-7-13-22(17-21)29(32)33)24(19(2)28-18)27(31)36-16-15-34-3/h4-13,17,25,28H,14-16H2,1-3H3/b11-8+
• InChIKey: KJEBULYHNRNJTE-DHZHZOJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-methoxyethyl) 5-(3-phenylprop-2-en-1-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; 3-(2-methoxyethyl) 5-(2E)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: 3-(2-methoxyethyl) 5-(3-phenylprop-2-en-1-yl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; cilnidipine; 3-(2-methoxyethyl) 5-(2E)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; atelec
• Synonyms: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl (2E)-3-phenyl-2-propenyl ester; Cilnidipine; FRC 8653; Cilnidipine; Atelec; 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 2-Methoxyethyl (2E)-3-Phenyl-2-propenyl Ester, FRC-8653, Atelec, Cinalong, Siscard,; 3-CinnaMyl 5-(2-Methoxyethyl) 2,6-diMethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Database IDs

• CAS Number: 132203-70-4
• MDL Number: MFCD00865853
• PubChem SID: 162037539; 24892414
• PubChem CID: 5282138

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 4.1029077
• LogD (pH = 7.4): 4.1029077
• Log P: 4.1029077
• Molar Refractivity: 137.1352 cm^3
• Polarizability: 51.402103 Å^3
• Polar Surface Area: 117.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true
• Acid pKa: 19.46359

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥20 mg/mL; H2O: ≤2 mg/mL
• Apperance: light yellow powder; Pale Yellow Solid
• Melting Point: 97-99°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; protect from light
• RTECS: US7975550
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: calcium channe
• Mechanism of Action: Calcium channel blocker

Product Information

• Purity: ≥98% (HPLC); 97%
• Salt Data: Free Base
• Application(s): Antihypertensive agent; Cardiovascular agent
• Empirical Formula (Hill Notation): C27H28N2O7

DETAILS

Selleck Chemicals - S1293

Research Area: Neurological Disease
Biological Activity:
Cilnidipine is a calcium channel blocker. It is a dual blocker of L-type voltage-gated calcium channels in vascular smooth muscle and N-type calcium channels in sympathetic nerve terminals that supply blood vessels. [1]References on Cilnidipine[1] http://en.wikipedia.org/wiki/Cilnidipine, ,

Sigma Aldrich - C1493

Packaging
Protect from high temperatures.
Biochem/physiol Actions
Cilnidipine is a slow-acting Ca2+ channel blocker; antihypertensive; vasodilator; dual blocker of L-type voltage-gated Ca2+ channels in vascular smooth muscle and N-type Ca2+ channels in sympathetic nerve terminals that supply blood vessels. Cilnidipine may offer an advantage over nifedipine as the long term intake of the latter has been linked to increased risk of myocardial infarction and mortality in patients with coronary artery disease. Cilnidipine lowers blood pressure, but has less effect on sympathetic activity. Unlike nifedipine, cilnidipine does not inhibit PKC.

Toronto Research Chemicals - C441375

A dihydropyridine calcium channel blocker.

REFERENCES

• http://en.wikipedia.org/wiki/Cilnidipine
• Ikeda, K., et al.: Oyo Yakuri, 44, 433 (1992)
• Hosono, M., et al.: J. Pharmacobio-Dyn., 15, 547, (1992)
• Ishii, M.: Japan Pharmacol. Ther., 21, 59 (1992)
• Japan. Pat., 1988, Fujirebio, 63 208 573; CA, 110, 95014j, (synth, pharmacol)
• Oike, M. et al., Circ. Res., 1990, 67, 993, (pharmacol)
• Nakashima, M. et al., Jpn. J. Pharmacol., 1991, 57, 51, (pharmacol)
• Hatada, K. et al., J. Chromatogr., 1992, 583, 116, (hplc-ms)
• Yoshimoto, R. et al., J. Pharmacobio-Dyn., 1992, 15, 25, (pharmacol)
• Uneyama, H. et al., Cardiovasc. Drug Rev., 1999, 17, 341-357, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 841