3-{1-[(3,3-diphenylpropyl)(methyl)amino]-2-methylpropan-2-yl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 410
• Molecular Formular: C36H41N3O6
• Molecular Mass: 611.72724
• Monoisotopic Mass: 611.29953605
• SMILES: O(C(CN(CCC(c1ccccc1)c1ccccc1)C)(C)C)C(=O)C1=C(NC(=C(C1c1cc([N+](=O)[O-])ccc1)C(=O)OC)C)C
• Canonical SMILES: COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC(CN(CCC(c1ccccc1)c1ccccc1)C)(C)C)C
• InChI: InChI=1S/C36H41N3O6/c1-24-31(34(40)44-6)33(28-18-13-19-29(22-28)39(42)43)32(25(2)37-24)35(41)45-36(3,4)23-38(5)21-20-30(26-14-9-7-10-15-26)27-16-11-8-12-17-27/h7-19,22,30,33,37H,20-21,23H2,1-6H3
• InChIKey: ZDXUKAKRHYTAKV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-[(3,3-diphenylpropyl)(methyl)amino]-2-methylpropan-2-yl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: @lercanidipine
• Brand Name: Lercanidipine [INN]
• Synonyms: lercanidipine; Lercanidipine

Database IDs

• CAS Number: 100427-26-7
• PubChem SID: 46508865; 160963873
• PubChem CID: 65866

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.808035
• LogD (pH = 7.4): 4.450044
• Log P: 6.4098167
• Molar Refractivity: 177.853 cm^3
• Polarizability: 67.42021 Å^3
• Polar Surface Area: 113.69 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.42
• LOG S: -6.59
• Solubility (Water): 1.56e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 6.4

DETAILS

DrugBank - DB00528

• Drug Groups: approved; investigational
• Description: Lercanidipine is a calcium channel blocker of the dihydropyridine class.; ; It is sold under various commercial names including Zanidip.
• Indication: For the treatment of Hypertension, management of angina pectoris and Raynaud's syndrome
• Pharmacology: Lercanidipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Lercanidipine is similar to other peripheral vasodilators. Lercanidipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.
• Affected Organisms: Humans and other mammals
• References: Lin TH, Voon WC, Yen HW, Huang CH, Su HM, Lai WT, Sheu SH: Lercanidipine and losartan effects on blood pressure and fibrinolytic parameters. Kaohsiung J Med Sci. 2006 Apr;22(4):177-83. [Pubmed] ; Martinez ML, Lopes LF, Coelho EB, Nobre F, Rocha JB, Gerlach RF, Tanus-Santos JE: Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension. J Cardiovasc Pharmacol. 2006 Jan;47(1):117-22. [Pubmed] ; Agrawal R, Marx A, Haller H: Efficacy and safety of lercanidipine versus hydrochlorothiazide as add-on to enalapril in diabetic populations with uncontrolled hypertension. J Hypertens. 2006 Jan;24(1):185-92. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Martinez ML, Lopes LF, Coelho EB, Nobre F, Rocha JB, Gerlach RF, Tanus-Santos JE: Lercanidipine reduces matrix metalloproteinase-9 activity in patients with hypertension. J Cardiovasc Pharmacol. 2006 Jan;47(1):117-22. Pubmed
• Agrawal R, Marx A, Haller H: Efficacy and safety of lercanidipine versus hydrochlorothiazide as add-on to enalapril in diabetic populations with uncontrolled hypertension. J Hypertens. 2006 Jan;24(1):185-92. Pubmed
• Lin TH, Voon WC, Yen HW, Huang CH, Su HM, Lai WT, Sheu SH: Lercanidipine and losartan effects on blood pressure and fibrinolytic parameters. Kaohsiung J Med Sci. 2006 Apr;22(4):177-83. Pubmed