Nicardipine

Base Information

• Chemical Name: Nicardipine
• CAS No.: 55985-32-5
• Molecular Formula: C26H29 N3 O6
• Molecular Weight: 479.533
• European Community (EC) Number: 259-932-3
• UNII: CZ5312222S
• DSSTox Substance ID: DTXSID6023363
• Wikipedia: Nicardipine
• Wikidata: Q729213
• NCI Thesaurus Code: C66879
• RXCUI: 7396
• Pharos Ligand ID: NPG251WB2WCQ
• Metabolomics Workbench ID: 42949
• ChEMBL ID: CHEMBL1484,CHEMBL3302409
• Mol file: 55985-32-5.mol

Synonyms:Antagonil;Cardene;Cardene I.V.;Cardene SR;Dagan;Flusemide;Hydrochloride, Nicardipine;LA, Nicardipine;Lecibral;Lincil;Loxen;Lucenfal;Nicardipine;Nicardipine Hydrochloride;Nicardipine LA;Nicardipino Ratiopharm;Nicardipino Seid;Perdipine;Ridene;Vasonase;Y 93;Y-93;Y93

Chemical Property of Nicardipine

Chemical Property:

• Melting Point: 136-138 ºC
• Boiling Point: 603.4 °C at 760 mmHg
• PKA: 7.30±0.50(Predicted)
• Flash Point: 318.7 °C
• PSA: 113.69000
• Density: 1.23 g/cm³
• LogP: 4.52980
• Solubility.: Dichloromethane; Methanol
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 479.20563565
• Heavy Atom Count: 35
• Complexity: 856

Purity/Quality:

99.9% ^*data from raw suppliers

Nicardipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Cardiovascular Agents
• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OCCN(C)CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OC
• Recent ClinicalTrials: The Intra-arterial Vasospasm Trial
• Recent EU Clinical Trials: Pregnancy reLated Acute hyperTension INtervention Action: a randomized trial comparing labetalol and nicardipine in women with acute hypertension in pregnancy (Platina-trial)
• Recent NIPH Clinical Trials: The accuracy of surgical pleth index (SPI) according to nicardipine or remifentanil intravenous infusion by comparing numerical changes of SPI value and end-tidal desflurane concentration during thyroid surgery: a prospective, single-centered, randomized , double-blind study.
• Uses: Vasodilator. It is used for arterial hypertension, chronic, stable angina pectoris, preventing angina pectoris, and for ischemic-type abnormalities of brain blood flow. Nicardipine is a dihydropyridine calcium channel blocker. Antianginal; antihypertensive. Neuroprotective & Neuroresearch products.
• Therapeutic Function: Vasodilator

Technology Process of Nicardipine

There total 15 articles about Nicardipine 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: 77.0%

2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-[2-(toluene-4-sulfonyloxy)-ethyl] ester (103785-48-4) + benzyl-methyl-amine (103-67-3) → Nicardipine (55985-32-5)

Guidance literature:

for 8h; Heating;

DOI:10.1248/cpb.34.1589

Reference yield: 67.0%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + (S)-1,1-Dibenzyl-3-[(R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-piperidinium; bromide → Nicardipine (55985-32-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1080/00397919708005632

Reference yield: 32.0%

2-(N-benzyl-N-methyl)amino-1-ethanol (101-98-4) + (S)-1-Benzyl-3-[(R)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-1-methyl-piperidinium; iodide → Nicardipine (55985-32-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 25 ℃;

DOI:10.1080/00397919708005632

upstream raw materials:

2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-[2-(toluene-4-sulfonyloxy)-ethyl] ester

benzyl-methyl-amine

2-(N-benzyl-N-methyl)amino-1-ethanol

(R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-piperidin-3-yl) ester 5-methyl ester

Downstream raw materials:

nisoldipine

C₂₆H₂₃⁽²⁾H₆N₃O₆

methyl 2-(N-methylamino)ethyl 4-(m-aminophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester

Refernces

• 1、 -. "ANTIHYPERTENSIVE THERAPY". . . Retrieved 2009/09/08.
• 2、 Kinugawa, Masahiko,Ogasa, Takehiro. "Facile synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetric dicarboxylates via quaternary ammonium salts of 2-aminoethyl 1,4-dihydropyridine-3,5-dicarboxylates". . p. 3321 - 3331. Retrieved 2007/10/03.