Levamlodipine

Base Information

• Chemical Name: Levamlodipine
• CAS No.: 103129-82-4
• Molecular Formula: C20H25ClN2O5
• Molecular Weight: 408.882
• UNII: 0P6NLP6806
• DSSTox Substance ID: DTXSID50904504
• Nikkaji Number: J512.131K
• Wikipedia: Levamlodipine
• Wikidata: Q6534831
• NCI Thesaurus Code: C166430
• RXCUI: 2376944
• Pharos Ligand ID: LXR1A1LH54A9
• Metabolomics Workbench ID: 58764
• ChEMBL ID: CHEMBL2111097
• Mol file: 103129-82-4.mol

Synonyms:2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-3-ethoxy-carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine;levamlodipine

Chemical Property of Levamlodipine

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 102-104°C
• Refractive Index: 1.546
• Boiling Point: 527.2 °C at 760 mmHg
• PKA: 8.97±0.10(Predicted)
• Flash Point: 272.6 °C
• PSA: 99.88000
• Density: 1.227 g/cm³
• LogP: 3.29540
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 408.1451996
• Heavy Atom Count: 28
• Complexity: 647

Purity/Quality:

99%, ^*data from raw suppliers

(S)-Amlodipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
• Isomeric SMILES: CCOC(=O)C1=C(NC(=C([C@@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
• Recent ClinicalTrials: Efficacy and Safety of Leningrado Association in the Treatment of Hypertension
• Recent EU Clinical Trials: Efficacy and safety of Concor 5mg plus amlodipine 5mg in hypertensive patients whose blood pressure cannot be controlled under 5mg of amlodipine monotherapy, a phase III multicentre, randomised, double-blind, clinical trial
• Uses: (S)-Enantiomer of Amlodipine (A633495). A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer. (S)-Enantiomer of Amlodipine. A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer.

Technology Process of Levamlodipine

There total 23 articles about Levamlodipine 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: 93.9%

S-(-)-amlodipine-hemi-D-tartrate mono-dimethylsulfoxide solvate → amlodipine (103129-82-4)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.666667h;

Reference yield: 93.0%

2C20H25ClN2O5*C24H17NO10 → amlodipine (103129-82-4)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.5h;

DOI:10.1021/op900070c

Reference yield: 92.0%

S(-) amlodipine-hemi L(+)-tartarate mono DMSO solvate → amlodipine (103129-82-4)

Guidance literature:

With ammonia; water; In dichloromethane; for 0.5h; Product distribution / selectivity;

upstream raw materials:

2-<(2-azidoethoxy)methyl>-4(S)-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-1,4-dihydropyridine

(-)-2-<<2-<(tert-butoxycarbonyl)amino>ethoxy>-methyl>-4-(2-chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridine

2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

(+)-2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-5-(methoxycarbonyl)-3-<(2(S)-methoxy-2-phenethoxy)carbonyl>-6-methyl-1,4-dihydropyridine

Downstream raw materials:

(S)-(-)-amlodipine nicotinate

(-)-Amlodipine maleate

(-)-Amlodipine besylate

(S)-(-)-amlodipine malonate salt

Refernces

• 1、 -. "Preparation method of levamlodipine benzenesulfonate (by machine translation)". Paragraph 0089-0091; 0093-0094. . Retrieved 2020/07/24.
• 2、 Liu, Min,Liu, Zhong-Qian,Zhu, Hai,He, Chao-Hong,Wu, Ke-Jun. "Enantioseparation of racemic amlodipine using immobilized ionic liquid by solid-phase extraction". . p. 1062 - 1071. Retrieved 2020/05/06.