Clevidipine butyrate CAS 167221-71-8

Introduction：Basic information about Clevidipine butyrate CAS 167221-71-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Clevidipine butyrate Basic information

• Product Name: Clevidipine butyrate
• Synonyms: Methyl (1-oxobutoxy)methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dime thyl-3,5-pyridinedicarboxylate;4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-Pyridinedicarboxylic acid methyl (1-oxobutoxy)methyl ester;3,5-Pyridinedicarboxylicacid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, 3-methyl5-[(1-oxobutoxy)methyl] ester;Clevidipine butyrate;Cleviprex;Clevidipine, Cleviprex;CS-136;CLEVELOX; CLEVIDIPINE
• CAS: 167221-71-8
• MF: C21H23Cl2NO6
• MW: 456.32
• EINECS: 682-702-2
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Clevidipine Butyrate impurity;Cardiovascular APIs;API
• Mol File: 167221-71-8.mol

Clevidipine butyrate Chemical Properties

• Melting point: 128-130°C
• Boiling point: 539.7±50.0 °C(Predicted)
• density: 1.289
• Fp: 280℃
• storage temp.: Keep in dark place,Inert atmosphere,2-8°C
• Water Solubility: Insoluble in water
• solubility: ≥21.4 mg/mL in DMSO; insoluble in H2O; ≥7.45 mg/mL in EtOH with ultrasonic
• pka: 2.45±0.70(Predicted)
• form: powder to crystal
• color: White to Light yellow
• InChI: 1S/C21H23Cl2NO6/c1-5-7-15(25)29-10-30-21(27)17-12(3)24-11(2)16(20(26)28-4)18(17)13-8-6-9-14(22)19(13)23/h6,8-9,18,24H,5,7,10H2,1-4H3
• InChIKey: KPBZROQVTHLCDU-UHFFFAOYSA-N
• SMILES: Clc1c(cccc1C2C(=C(NC(=C2C(=O)OC)C)C)C(=O)OCOC(=O)CCC)Cl
• CAS DataBase Reference: 167221-71-8

Safety Information

• Safety Statements: 24/25
• WGK Germany: WGK 3
• HS Code: 29339900
• Storage Class: 6.1D - Non-combustible acute toxic Cat.3 toxic hazardous materials or hazardous materials causing chronic effects
• Hazard Classifications: Acute Tox. 3 Oral Repr. 2

Clevidipine butyrate Usage And Synthesis

Description

Clevidipine is an ultra-short-acting vasodilator of the dihydropyridine(DHP) class of CCB. It is indicated as an intravenous treatment for theacute management of hypertension when oral therapy is not feasible ornot desirable. Clevidipine is the second intravenous CCB to be marketedbehind nicardipine for this indication. Both agents are primarily usedfor urgent treatment of hypertension in cardiac surgical setting, intensivecare units, and emergency departments. Other intravenous agentscurrently 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 effecton the myocardial contractility and venous capacitance. It has arapid onset and offset of action and a very short plasma half-life, whichallows 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.

Chemical Properties

White to Off-White Solid

Originator

AstraZeneca (United Kingdom)

Uses

Clevidipine butyrate is a dihydropyridine calcium channel blocker use as agent for the reduction of blood pressure。

Uses

Calcium channel blocker, used as an oral antihypertensive.

Uses

Clevidipine butyrate is a novel intravenous, short-actingcalcium channel blocker that provides quick and accuratecontrol of blood pressure in an emergency setting. Unlikeother 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 thusavoids accumulation. The drug was launched by MedicinesCompany which aquired the rights from AstraZeneca.

Uses

A calcium channel protein inhibitor and blocker

Definition

ChEBI: Clevidipine is a dihydropyridine.

Brand name

Clevelox (The Medicines Company).

Side effects

Clevidipine is contraindicated in patients with severe aortic stenosis, defective lipid metabolism, and allergies to eggs, egg products, soybeans, or soy products. The chemical synthesis of clevidipine entails the esterification of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester with chloromethyl butyrate by the action of potassium bicarbonate in refluxing acetonitrile.

Synthesis

The chemical synthesis of clevidipine entails the esterification of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester with chloromethyl butyrate by the action of potassium bicarbonate in refluxing acetonitrile. The DHP-monoester starting material is obtained in two steps through condensation of methyl 2,3-dichlorobenzylidine acetoacetate and 2-cyanoethyl ester of 2-amino-2-propenoic acid to the DHP diester, followed by base catalyzed cleavage of the cyanoethyl group. Clevidipine is practically insoluble in water and is formulated in an oil-inwater emulsion.