Amlodipine

Base Information

• Chemical Name: Amlodipine
• CAS No.: 88150-42-9
• Molecular Formula: C20H25ClN2O5
• Molecular Weight: 408.882
• Hs Code.: 2942000000
• European Community (EC) Number: 425-820-1,618-119-7
• UNII: 1J444QC288
• DSSTox Substance ID: DTXSID7022596
• Nikkaji Number: J33.383B
• Wikipedia: Amlodipine
• Wikidata: Q411347
• NCI Thesaurus Code: C61635
• RXCUI: 17767
• Pharos Ligand ID: LXRLU18NWBGK
• Metabolomics Workbench ID: 145124
• ChEMBL ID: CHEMBL1491,CHEMBL3304444,CHEMBL3211346
• Mol file: 88150-42-9.mol

Synonyms:Amlodipine;Amlodipine Besylate;Amlodipine Maleate;Amlodipine Maleate (1:1);Amlodipine, (+-)-Isomer;Amlodipine, (+-)-Isomer, Maleate (1:1);Amlodipine, (R)-Isomer;Amlodipine, (S)-Isomer, Maleate (1:1);Amlodis;Amlor;Astudal;Istin;Norvasc

Chemical Property of Amlodipine

Chemical Property:

• Appearance/Colour: Yellow solid
• Melting Point: 178-179 °C
• Boiling Point: 527.2 °C at 760 mmHg
• PKA: pKa 8.6 (Uncertain)
• Flash Point: 272.6 °C
• PSA: 99.88000
• Density: 1.227 g/cm³
• LogP: 3.29540
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in DMSO (up to 25 mg/ml), in DMF (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• Water Solubility.: 75.3 mg/L
• 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

Amlodipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Cardiovascular Agents
• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
• Recent ClinicalTrials: Zilebesiran as Add-on Therapy in Patients With Hypertension Not Adequately Controlled by a Standard of Care Antihypertensive Medication (KARDIA-2)
• Recent EU Clinical Trials: The effects of medication induced blood pressure reduction on cerebral hemodynamics in hypertensive frail elderly
• Recent NIPH Clinical Trials: ESPIAL TRIAL
• Description: Amlodipine is a dihydropyridine L-type calcium channel blocker that selectively inhibits calcium influx in cardiac and vascular smooth muscle. Acting as a vasodilator, amlodipine reduces blood pressure by relaxing the smooth muscle in the arterial wall, decreasing total peripheral resistance. It inhibits calcium-induced contractions in depolarized rat aorta with an IC50 value of 1.9 nM, displaying a slow rate of association and dissociation in isolated vascular and cardiac tissues. Amlodipine also demonstrates actions independent of L-type calcium channel blockade by regulating membrane fluidity and cholesterol deposition, stimulating nitric oxide production, acting as an antioxidant, and regulating matrix deposition in vitro and in vivo. Formulations containing amlodipine have been used in the treatment of hypertension.
• Uses: A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer. anti-hypertensive;calcium channel blocker A deuterated dihydropyridine calcium channel blocker.;Application of Labeled APIs: Labeled Amlodipine, intended for use as an internal standard for the quantification of Amlodipine by GC- or LC-mass spectrometry.
• Clinical Use: Calcium-channel blocker: Hypertension Angina prophylaxis
• Drug interactions: Potentially hazardous interactions with other drugs Aminophylline and theophylline: possibly increased aminophylline and theophylline concentration. Anaesthetics: enhanced hypotensive effect. Antibacterials: metabolism possibly inhibited by clarithromycin, erythromycin and telithromycin. Antidepressants: enhanced hypotensive effect with MAOIs, concentration possibly reduced by St John’s wort. Antiepileptics: effects probably reduced by phenobarbital and primidone. Antifungals: negative inotropic effect possibly increased with itraconazole. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect of postsynaptic alpha-blockers. Antivirals: concentration increased by telaprevir and possibly by ritonavir - reduce dose of amlodipine. Ciclosporin: ciclosporin concentration may be increased by up to 40%. Lipid lowering agents: possibly increased risk of myopathy - do not exceed 20 mg of simvastatin.1 Tacrolimus: possibly increased tacrolimus levels.

Technology Process of Amlodipine

There total 14 articles about Amlodipine 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: 93.1%

2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester (113994-41-5) → 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9)

Guidance literature:

With sodium cyanoborohydride; acetic acid; at 15 - 25 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 88.6%

amlodipine besylate (111470-99-6) → 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9)

Guidance literature:

With sodium hydroxide; In water; for 0.5h; Heating / reflux;

Reference yield: 87.2%

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine (88150-62-3,103094-30-0) → 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9)

Guidance literature:

With ethanol; methylamine; at 28 - 32 ℃; for 17h;

upstream raw materials:

2-(2-azidoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine

ethyl (2-chloroaceto)acetate

ethyl 4-(2-azidoethoxy)acetoacetate

Downstream raw materials:

amlodipine p-toluene sulfonate

C₃₂H₄₉ClN₂O₁₁

Refernces

• 1、 -. "Method for preparing levamlodipine". . . Retrieved 2020/10/14.
• 2、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.