167221-71-8 Usage
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.
Chemical Properties
White to Off-White Solid
Originator
AstraZeneca (United Kingdom)
Uses
Different sources of media describe the Uses of 167221-71-8 differently. You can refer to the following data:
1. Clevidipine butyrate is a dihydropyridine calcium channel blocker use as agent for the reduction of blood pressure。
2. Calcium channel blocker, used as an oral antihypertensive.
3. 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.
4. A calcium channel protein inhibitor and blocker
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.
Check Digit Verification of cas no
The CAS Registry Mumber 167221-71-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,7,2,2 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 167221-71:
(8*1)+(7*6)+(6*7)+(5*2)+(4*2)+(3*1)+(2*7)+(1*1)=128
128 % 10 = 8
So 167221-71-8 is a valid CAS Registry Number.
InChI:InChI=1/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
167221-71-8Relevant articles and documents
Butyric acid clevidipine preparation method
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, (2017/01/17)
The invention discloses a preparation method of clevidipine butyrate, comprising the following steps: (1) carrying out one-pot reaction by putting 2,3-dichlorobenzaldehyde, methyl acetoacetate and 3-amino crotonic acid ethyl cyanide in a solvent under the action of a catalyst; (2) carrying out recrystallization to obtain a pure product (+/-)-3-(2-cyanoethyl)-5-methyl-4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid; (3) carrying out a reaction between the pure product and alkali; (4) adding water and hydrochloric acid, and collecting an intermediate from reaction products; and (5) carrying out a reaction between the intermediate and n-chloromethyl butyrate in the presence of an alkaline substance and an iodide catalyst, and finally collecting the target product clevidipine butyrate from reaction products. The preparation method provided by the invention has advantages of high yield, stable product quality and low cost, is simple to operate, and is suitable for industrial product of clevidipine butyrate.
PROCESS FOR PREPARATION OF CLEVIDIPINE AND ITS INTERMEDIATE
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Page/Page column 6, (2012/06/15)
The present invention relates to a process for the removal of t-butyl group from t-butyl methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate to provide-1,4-dihydro-2,6-dimethyl-4-(2',3'-dichorophenyl)-5-methoxycarbonyl-3-pyr
PREPARATION OF DIHYDROPYRIDINES
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Page/Page column 12, (2011/11/13)
The invention relates to a method and compounds for the preparation of clevidipine butyrate, a very short acting hypertensive calcium antagonist, as well as the synthesis of these compounds useful for the preparation of clevidipine (also known as clevidip
