Clevidipine

Base Information

• Chemical Name: Clevidipine
• CAS No.: 167221-71-8
• Deprecated CAS: 166432-28-6
• Molecular Formula: C₂₁H₂₃Cl₂NO₆
• Molecular Weight: 456.323
• Hs Code.: 29339900
• European Community (EC) Number: 682-702-2,814-032-5
• UNII: 19O2GP3B7Q
• DSSTox Substance ID: DTXSID6057661
• Nikkaji Number: J772.200A
• Wikipedia: Clevidipine
• Wikidata: Q5132338
• NCI Thesaurus Code: C72727
• RXCUI: 233603
• Pharos Ligand ID: 9YMDM8K1B9GQ
• Metabolomics Workbench ID: 149336
• ChEMBL ID: CHEMBL1237132
• Mol file: 167221-71-8.mol

Synonyms:butyroxymethyl methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate;clevidipine;Cleviprex

Chemical Property of Clevidipine

Chemical Property:

• Appearance/Colour: Powder
• Melting Point: 128-130°C
• Boiling Point: 539.7 °C at 760 mmHg
• PKA: 2.45±0.70(Predicted)
• Flash Point: 280.2 °C
• PSA: 90.93000
• Density: 1.289 g/cm³
• LogP: 4.57400
• Storage Temp.: Refrigerator
• Solubility.: ≥21.4 mg/mL in DMSO; insoluble in H2O; ≥7.45 mg/mL in EtOH with ultrasonic
• Water Solubility.: Insoluble in water
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 455.0902428
• Heavy Atom Count: 30
• Complexity: 748

Purity/Quality:

99% ^*data from raw suppliers

Clevidipine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)OCOC(=O)C1=C(NC(=C(C1C2=C(C(=CC=C2)Cl)Cl)C(=O)OC)C)C
• Recent ClinicalTrials: Clevidipine Infusion for Blood Pressure Management After Successful Revascularization in Acute Ischemic Stroke
• Recent EU Clinical Trials: A Safety and Efficacy Study of Blood Pressure Control in Acute Heart Failure – A Pilot Study (PRONTO)
• Description: Clevidipine is an ultra-short-acting vasodilator of the dihydropyridine (DHP) class of CCB. It is indicated as an intravenous treatment for the acute management of hypertension when oral therapy is not feasible or not desirable. Clevidipine is the second intravenous CCB to be marketed behind nicardipine for this indication. Both agents are primarily used for urgent treatment of hypertension in cardiac surgical setting, intensive care units, and emergency departments. Other intravenous agents currently on the market for this indication include sodium nitroprusside, nitroglycerin, fenoldopam, hydralazine, esmolol, and labetalol. Clevidipine is a potent, arterial-specific, vasodilator with very little or no effect on the myocardial contractility and venous capacitance. It has a rapid onset and offset of action and a very short plasma half-life, which allows for titration of the drug to achieve precise BP control.clevidipine is exclusively metabolized in the blood and the tissues. It does not undergo any renal or hepatic metabolism and does not accumulate in the body. Clevidipine is a blocker of L-type calcium channels, which mediate the influx of calcium during depolarization in arterial smooth muscle.
• Uses: Clevidipine butyrate is a dihydropyridine calcium channel blocker use as agent for the reduction of blood pressure。 Calcium channel blocker, used as an oral antihypertensive. Clevidipine butyrate is a novel intravenous, short-acting calcium channel blocker that provides quick and accurate control of blood pressure in an emergency setting. Unlike other intravenous hypertension drugs which are metabolized in kidney or liver and tend to accumulate in the body, clevidipine is metabolized in the blood and tissues and thus avoids accumulation. The drug was launched by Medicines Company which aquired the rights from AstraZeneca. A calcium channel protein inhibitor and blocker

Technology Process of Clevidipine

There total 14 articles about Clevidipine 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: 90.0%

potassium 4-(2',3'-dichlorophenyl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylate + chloromethyl n-butyrate (33657-49-7) → clevidipine (166432-28-6,167221-71-8)

Guidance literature:

In acetonitrile; for 3.5h; Heating / reflux;

Reference yield: 87.2%

chloromethyl n-butyrate (33657-49-7) + (+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid (123853-39-4) → clevidipine (166432-28-6,167221-71-8)

Guidance literature:

With potassium carbonate; lithium iodide; In N,N-dimethyl-formamide; at 70 ℃; for 4h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 74.0%

sodium 4-(2',3'-dichlorophenyl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylate + chloromethyl n-butyrate (33657-49-7) → clevidipine (166432-28-6,167221-71-8)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; for 5h; Heating / reflux;

upstream raw materials:

chloromethyl n-butyrate

(+)-4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-3-pyridinecarboxylic acid

2-(2',3'-dichloro-benzylidene)-3-oxo-butyric acid butyryloxymethyl ester

methyl 3-aminocrotonate

Refernces

• 1、 -. "Butyric acid clevidipine synthetic method". Paragraph 0052-0054. . Retrieved 2016/10/10.
• 2、 -. "PREPARATION OF INTERMEDIATES FOR THE SYNTHESIS OF DIHYDROPYRIDINE CALCIUM CHANNEL BLOCKERS". Page/Page column 7. . Retrieved 2011/11/06.