Amlodipine Besylate

Base Information

• Chemical Name: Amlodipine Besylate
• CAS No.: 111470-99-6
• Molecular Formula: C20H25ClN2O5^.C6H6O3S
• Molecular Weight: 567.06
• Hs Code.: 29333990
• European Community (EC) Number: 658-042-6
• NSC Number: 758922
• UNII: 864V2Q084H
• DSSTox Substance ID: DTXSID2043909
• Wikidata: Q27105760
• NCI Thesaurus Code: C28820
• RXCUI: 104416
• ChEMBL ID: CHEMBL1200402,CHEMBL3193637,CHEMBL3207778
• Mol file: 111470-99-6.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 Besylate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 3.34E-11mmHg at 25°C
• Melting Point: 199-201 ºC
• Boiling Point: 527.2 ºC at 760 mmHg
• PKA: 8.6
• Flash Point: 272.6 ºC
• PSA: 162.63000
• Density: 1.227 g/cm³
• LogP: 5.30950
• Storage Temp.: Store at RT
• Solubility.: DMSO: 20 mg/mL
• Water Solubility.: Soluble in DMSO (20 mg/mL), water (10 mM), chloroform, ethanol (14 mg/mL), and methanol.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 566.1489648
• Heavy Atom Count: 38
• Complexity: 830

Purity/Quality:

99.00% ^*data from raw suppliers

Amlodipine Besylate ≥99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN.C1=CC=C(C=C1)S(=O)(=O)O
• Recent ClinicalTrials: Mechanism of Hypertension Treatments in Liver Transplant Recipients (BLOCK LTR-HTN)
• Recent EU Clinical Trials: Evaluation of the clinical efficacy and safety of perindopril 10 mg/indapamide 2.5 mg/amlodipine 5 or 10 mg/bisoprolol 5 mg in single-pill combination after 8 weeks of treatment versus the free combination of perindopril 10 mg, indapamide 2.5 mg and amlodipine 5 or 10 mg in patients with uncontrolled essential hypertension. An international, multicentre, randomised, double-blind, 16-week study.
• Recent NIPH Clinical Trials: Effect of on combination therapy with irbesartan and amlodipine besilate on clinical blood pressure, home blood pressure and blood pressure variability in hypertensive patients with chronic kidney disease
• Drug Classification and Use: Amlodipine besylate belongs to the class of calcium channel blockers (CCBs) and is primarily used to treat hypertension (high blood pressure). It is also utilized for the treatment of chronic stable angina and vasospastic angina.
• Pharmacokinetic Characteristics: Amlodipine besylate is a dihydropyridine CCB with unique pharmacokinetic properties attributed to its high degree of ionization. The drug is available in both racemic and enantiomer forms, with the (鈭?)-(S)-enantiomer being primarily responsible for its pharmacological activity.
• Mechanism of Action: Amlodipine besylate blocks the influx of calcium ions into cardiac and vascular muscles, leading to vasodilation and reduced blood pressure.
• Pharmaceutical Formulations: Amlodipine besylate is formulated into various dosage forms for oral administration, including tablets.; Fast-dissolving tablets of amlodipine besylate have been developed using the sublimation method, offering increased dissolution rates and improved bioavailability.
• Solid Forms and Crystal Structures: Amlodipine besylate exists in four solid forms: anhydrate, monohydrate, dihydrate, and amorphous.; Comprehensive characterization of these forms has been conducted using various analytical techniques such as X-ray diffraction, thermal analysis, spectroscopy, and microscopy.; The kinetic solubility rank order at 37掳C in water is found to be anhydrate > monohydrate > dihydrate, with the dihydrate being the most stable form under these conditions.; Other forms undergo solvent-mediated transformation (SMT) to yield the dihydrate.
• Dosage Equivalence: Amlodipine besylate is often dosed in terms of its free base equivalent, with 6.9 mg equivalent to 5 mg of amlodipine free base.
• Manufacturing Techniques: The direct compression process is used for manufacturing amlodipine besylate tablets due to its simplicity and cost-effectiveness compared to traditional granulation technologies.

Technology Process of Amlodipine Besylate

There total 14 articles about Amlodipine Besylate 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: 91.6%

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine (88150-62-3,103094-30-0) + benzenesulfonic acid (98-11-3) → amlodipine besylate (111470-99-6)

Guidance literature:

4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine; With methylamine; at 25 ℃; Large scale;

benzenesulfonic acid; In water; at 30 ℃; Temperature; Large scale;

Reference yield: 90.0%

amlodipine formate (246852-08-4) + sodium phenylsulfonate (515-42-4) → amlodipine besylate (111470-99-6)

Guidance literature:

In water; at 5 - 20 ℃; for 0.333333h; Product distribution / selectivity;

Reference yield: 89.0%

amlodipine chloroacetate (246852-11-9) + sodium phenylsulfonate (515-42-4) → amlodipine besylate (111470-99-6)

Guidance literature:

Product distribution / selectivity;

upstream raw materials:

N-tritylamlodipine

benzenesulfonic acid

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

amlodipine mesylate

Downstream raw materials:

amlodipine p-toluene sulfonate

(-)-Amlodipine besylate

(+)-Amlodipine besylate

amlodipine mesylate

Refernces

• 1、 -. "Synthesis process of amlodipine besylate". Paragraph 0006; 0014; 0015; 0027-0030. . Retrieved 2018/09/14.
• 2、 -. "Using the new crystal form [...] and production of high-purity [...]". Paragraph 0016; 0069; 0070; 0074. . Retrieved 2017/02/17.