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

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

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

Also known as: 100427-26-7, Lercanidipine [inn], Lercanil, Lercanidipine (inn), V7xtj4r0bh, Masnidipine

Molecular Formula

C₃₆H₄₁N₃O₆

Molecular Weight

611.7 g/mol

InChI Key

ZDXUKAKRHYTAKV-UHFFFAOYSA-N

FDA UNII

V7XTJ4R0BH

Lercanidipine is a calcium channel blocker of the dihydropyridine class. It is sold under various commercial names including Zanidip.

1 2D Structure

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

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

ZDXUKAKRHYTAKV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C(C(=C(N1)C)C(=O)OC(C)(C)CN(C)CCC(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC

2.2 Other Identifiers

2.2.1 UNII

V7XTJ4R0BH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lercadip

2. Lercanidipine Hydrochloride

3. Lerdip

4. Methyl-1,1-dimethyl-2-(n-(3,3-diphenylpropyl)-n-methylamino)ethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

5. Rec 15-2375

6. Rec-15-2375

7. Zanidip

2.3.2 Depositor-Supplied Synonyms

1. 100427-26-7

2. Lercanidipine [inn]

3. Lercanil

4. Lercanidipine (inn)

5. V7xtj4r0bh

6. Masnidipine

7. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-[2-[(3,3-diphenylpropyl)methylamino]-1,1-dimethylethyl] 5-methyl Ester

8. 5-o-[1-[3,3-diphenylpropyl(methyl)amino]-2-methylpropan-2-yl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

9. 1-[(3,3-diphenylpropyl)(methyl)amino]-2-methylpropan-2-yl Methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

10. 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

11. 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

12. Lercanil (tn)

13. Ncgc00167492-01

14. Unii-v7xtj4r0bh

15. Lercanidipine [inn:ban]

16. Lercanadipine

17. 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic Acid O5-[1-[3,3-diphenylpropyl(methyl)amino]-2-methylpropan-2-yl] Ester O3-methyl Ester

18. Lercanidipine [mi]

19. Schembl25268

20. Lercanidipine [who-dd]

21. Chembl250270

22. Schembl6846222

23. Dtxsid2048327

24. Chebi:135930

25. Hms3604g05

26. Bcp21318

27. Hy-b0612

28. Bbl029074

29. S5861

30. Stk639861

31. Akos005571238

32. Db00528

33. Sdccgsbi-0633690.p001

34. Ncgc00167492-02

35. Ncgc00167492-11

36. (+-)-2-((3,3-diphenylpropyl)methylamino)-1,1-dimethylethyl Methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate

37. Ac-15409

38. As-75252

39. Ft-0631006

40. C13971

41. D08111

42. 427l267

43. A800200

44. A929939

45. Q410492

46. Sr-01000884000

47. Sr-01000884000-1

48. [2-oxo-3-(3-trifluoromethyl-phenoxy)-propyl]-phosphonic

49. 2-((3,3-diphenylpropyl)methylamino)-1,1-dimethylethyl Methyl (4rs)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

50. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-((3,3-diphenylpropyl)methylamino)-1,1-dimethylethyl Methyl Ester

51. 3,5-pyridinedicarboxylic Acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-(3,3-diphenylpropyl)methylamino)-1,1-dimethylethyl Methyl Ester

52. O5-[1-[3,3-diphenylpropyl(methyl)amino]-2-methyl-propan-2-yl] O3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₆H₄₁N₃O₆
Molecular Weight	611.7 g/mol
XLogP3	6.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	13
Exact Mass	611.29953604 g/mol
Monoisotopic Mass	611.29953604 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	1090
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of Hypertension, management of angina pectoris and Raynaud's syndrome

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Calcium Channel Blockers

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

5.3 ATC Code

C08CA13

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA13 - Lercanidipine

5.4 Mechanism of Action

By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, Lercanidipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes 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.