Lercanidipine

Base Information

• Chemical Name: Lercanidipine
• CAS No.: 100427-26-7
• Molecular Formula: C36H41N3O6
• Molecular Weight: 611.738
• Hs Code.: 2942000000
• European Community (EC) Number: 807-432-6
• UNII: V7XTJ4R0BH
• DSSTox Substance ID: DTXSID2048327
• Wikipedia: Lercanidipine
• Wikidata: Q410492
• NCI Thesaurus Code: C81687
• Pharos Ligand ID: LL3CDGAUT7RF
• Metabolomics Workbench ID: 42867
• ChEMBL ID: CHEMBL250270
• Mol file: 100427-26-7.mol

Synonyms:Lercadip;lercanidipine;lercanidipine hydrochloride;Lerdip;methyl-1,1-dimethyl-2-(N-(3,3-diphenylpropyl)-N-methylamino)ethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;REC 15-2375;REC-15-2375;Zanidip

Chemical Property of Lercanidipine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.77E-20mmHg at 25°C
• Melting Point: 118-120 °C
• Refractive Index: 1.579
• Boiling Point: 712.5 °C at 760 mmHg
• Flash Point: 384.7 °C
• PSA: 113.69000
• Density: 1.177 g/cm³
• LogP: 7.33040
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 611.29953604
• Heavy Atom Count: 45
• Complexity: 1090

Purity/Quality:

99% ^*data from raw suppliers

Lercanidipine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Recent ClinicalTrials: Bariatric Surgery and Pharmacokinetics of Lercanidipine
• Recent EU Clinical Trials: Prospective, randomized, open-label, blinded-endpoint, paralell groups, multicentric clinical trial to compare the efficacy of administration of enalapril 20 mg + lercanidipine 10 mg versus enalapril 20 mg + amlodipine 5 mg on proteinuria.
• Description: Lerdip was launched in the Netherlands for hypertension. It is prepared in four steps, the last of which is a Hantsch reaction of 1-[(3,3-diphenyl)-N-methylpropylamino]- 2-methyl-2-propyl-2-(3-nitrobenzylidene)acetoacetate with methyl 3-aminocrotonate. This compound was designed to be very lipophilic which imparts the drug with a gradual onset and a long duration of action as a result of prolonged exposure to receptors by partitioning into membranes. It is an antagonist of L-type calcium channels with no activity in smooth muscle cells, is tissue selective, lacks any myocardial contractility impairment, has no neuroendocrine activation, and has negligible affinity for neurotransmitter receptors such as α1- and α2-adrenergic receptors. While sold as a racemate, the calcium channel activity is found in the (S)- isomer with the (R)-isomer being 2-orders of magnitude less active. It has an increased cardiac contractility index which is much more than Nitrendipine or nifedipine. The good selectivity causes a reduction in blood pressure with no negative inotropic effects.
• Uses: Antihypertensive compound; calcium channel blocker.

Technology Process of Lercanidipine

There total 10 articles about Lercanidipine 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: 99.5%

2,N-dimethyl-2-(trimethylsilyloxy)-N-(3,3-diphenylpropyl)-1-propanamine + 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride (88712-56-5,125185-92-4) → lercanidipine (100427-26-7)

Guidance literature:

2,N-dimethyl-2-(trimethylsilyloxy)-N-(3,3-diphenylpropyl)-1-propanamine; 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride; In dichloromethane; at -10 - 30 ℃; for 2h;

With water; In dichloromethane; at 5 - 10 ℃; for 0.25h;

Reference yield: 77.1%

lercanidipine hydrochloride (132866-11-6,184866-29-3) → lercanidipine (100427-26-7)

Guidance literature:

With sodium methylate; In methanol; at 20 - 25 ℃; for 4.5h; Product distribution / selectivity;

Reference yield:

1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride (88712-56-5,125185-92-4) + 2,N-dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol (100442-33-9) → lercanidipine (100427-26-7)

Guidance literature:

In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 3h; Yield given;

DOI:10.1016/S0223-5234(98)80015-9

upstream raw materials:

1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride

2,N-dimethyl-N-(3,3-diphenylpropyl)-1-amino-2-propanol

methyl 3-aminocrotonate

2-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-3-oxo-butyric acid 2-[(3,3-diphenyl-propyl)-methyl-amino]-1,1-dimethyl-ethyl ester

Downstream raw materials:

methyl 1,1,N-trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate maleate

methyl 1,1,N-trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate L-lactate

methyl 1,1,N-trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate salicylate

methyl 1,1,N-trimethyl-N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate cinnamate

Refernces

• 1、 -. "ANTIHYPERTENSIVE THERAPY". . . Retrieved 2009/09/08.
• 2、 -. "A NOVEL PROCESS FOR THE PREPARATION OF LERCANIDIPINE". . . Retrieved 2008/06/13.