3-methyl 5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 4449
• Molecular Formular: C19H19N3O6
• Molecular Mass: 385.37066
• Monoisotopic Mass: 385.12738534
• SMILES: CC1=C(C(C(=C(N1)C#N)C(=O)OC)c1cc(ccc1)[N+](=O)[O-])C(=O)OC(C)C
• Canonical SMILES: COC(=O)C1=C(C#N)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC(C)C)C
• InChI: InChI=1S/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3
• InChIKey: FAIIFDPAEUKBEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl 5-propan-2-yl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: escor; nilvadipine
• Brand Name: Nivadil
• Synonyms: Nilvadipine; 2-Cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl 5-(1-Methylethyl) Ester, FR-34235, SKF-102362, Escor,; Nilvadipine (ARC029)

Database IDs

• CAS Number: 75530-68-6
• PubChem SID: 99443264; 160967881
• PubChem CID: 4494

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.2390466
• LogD (pH = 7.4): 2.2390466
• Log P: 2.2390466
• Molar Refractivity: 100.7934 cm^3
• Polarizability: 37.528217 Å^3
• Polar Surface Area: 131.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 18.247496

ALOGPS 2.1

• Log P: 2.97
• LOG S: -4.49
• Solubility (Water): 1.24e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Solid
• Melting Point: 148-150°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: Calcium Channel

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB06712

• Drug Groups: approved
• Description: Nilvadipine is a calcium channel blocker (CCB) for treatment of hypertension.
• Indication: For the management of vasospastic angina, chronic stable angina and hypertension.
• Pharmacology: Nilvadipine is similar to other dihydropyridines including amlodipine, felodipine, isradipine, and nicardipine. Nilvadipine is used to treat Prinzmetal's angina, hypertension, and other vascular disorders such as Raynaud's phenomenon. By blocking the calcium channels, Nifedipine inhibits the spasm of the coronary artery and dilates the systemic arteries, results in a increase of myocardial oxygen supply and a decrease in systemic blood pressure.
• External Links: Wikipedia

Toronto Research Chemicals - N475150

Used as an antihypertensive and antianginal.

REFERENCES

• Gross, G.J., et al.: Gen. Pharmacol., 14, 677 (1983)
• Molyvdas, P.A. and Sperelakis, N.: J. Cardiovasc. Pharmacol., 8, 449 (1983)
• Mizuno, K., et al.: Res. Comm. Chem. Pathol. Pharmacol., 52, 3 (1986)