Carvedilol

Carvedilol Basic information
Product Name:Carvedilol
Synonyms:1-(9h-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-2-propano;1-(9H-CARBAZOL-4-YLOXY)-3-[[2-(2-METHOXYPHENOXY)ETHYL]AMINO]-2-PROPANOL;CARVEDILOL;COREG;DIMITONE;DQ-2466;DILATREND;BM-14190
CAS:72956-09-3
MF:C24H26N2O4
MW:406.47
EINECS:1308068-626-2
Product Categories:LEVAQUIN;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;Cardiovascular Drugs;Active Pharmaceutical Ingredients;API's;Adrenoceptor;Aromatics;APIs
Mol File:72956-09-3.mol
Carvedilol Structure
Carvedilol Chemical Properties
Melting point 113-117°C
Boiling point 655.2±55.0 °C(Predicted)
density 1.250±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >20mg/mL
form solid
pka13.90±0.20(Predicted)
color white to off-white
Water Solubility 449.2ug/L(22.5 ºC)
Merck 14,1873
CAS DataBase Reference72956-09-3(CAS DataBase Reference)
Safety Information
Hazard Codes N,Xn
Risk Statements 51/53-36/37/38-20/21/22
Safety Statements 61-36-26
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS UA8670000
HazardClass IRRITANT
PackingGroup III
HS Code 2933995300
Hazardous Substances Data72956-09-3(Hazardous Substances Data)
ToxicityLD50 oral in dog: > 1gm/kg
MSDS Information
ProviderLanguage
Carvedilol English
Carvedilol Usage And Synthesis
DescriptionCarvedilol is a vasodilating beta-blocker useful in the treatment of hypertension and angina pectoris. In addition to lowering blood pressure, carvedilol decreases total vascular resistance without the reflex tachycardia usually occurring with vasodilators. It is reported to be well tolerated with renal sparing effects.
DescriptionCarvedilol (Item No. 26286) is an analytical reference standard categorized as a β-adrenergic receptor antagonist and vasodilator. Formulations containing carvedilol have been used to enhance physical performance in athletes. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .
Chemical PropertiesColourless Crystalline Solid
OriginatorBoehringer Mannheim (Germany)
UsesA nonselective -adrenergic blocker with a1-blocking activity. An antihypertensive used in the treatment of congestive heart failure.
Usesantibacterial
UsesCarvedilol is a nonselective β-adrenergic blocker with α1-blocking activity. Carvedilol is an antihypertensive used in the treatment of congestive heart failure.
Usesveterinary use
UsesFor the treatment of mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin.
UsesAn α1- and β-adrenergic receptor antagonist.
DefinitionChEBI: A member of the class of carbazoles that is an adrenergic antagonist with non-selective beta- and alpha-1 receptor blocking properties which helps in the management of congestive heart failure.
Manufacturing Process1-(9H-Carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-2-propanol may be synthesized by the method of preparation of S-(-)-(1-carbazol-4- yloxy)-3-[2-(2-methoxyphenoxy)]ethylaminopropan-2-ol (Patent US 4,697,022 and 4,824,963).
27.5 g 4-hydroxycarbazole are dissolved in a mixture of 150 ml 1 N aqueous sodium hydroxide solution and 70 ml dimethylsulfoxide. To this is added at ambient temperature 13.9 g epichlorohydrin, followed by stirring for 18 hours at ambient temperature. 280 ml water are then added thereto, followed by stirring for 15 min and filtering off with suction. The filter residue is washed with 0.1 N aqueous sodium hydroxide solution and water and subsequently dissolved in methylene chloride. The methylene chloride solution is dried over anhydrous sodium sulfate, treated with active charcoal and floridin and evaporated. 4-(2,3-Epoxypropoxy)-carbazole is purified by recrystallising twice from ethyl acetate. From the mother liquors there are isolated a further 4- (2,3-epoxypropoxy)-carbazole.
10 g 4-(2,3-epoxypropoxy)-carbazole are, together with 13.97 g o-methoxyphenoxyethylamine, heated under reflux in 70 ml isopropanol for 2 hours. The solvent is evaporated off and the residue is stirred for 2 hours with a mixture of 115 ml toluene, 35 ml cyclohexane and 40 ml ethyl acetate. After filtering off with suction, the (1-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)]-ethylaminopropan-2-ol is recrystallised from 150 ml ethyl acetate.

Brand nameCoreg (GlaxoSmithKline);Dilatrend.
Therapeutic FunctionBeta-adrenergic blocker
General DescriptionCarvedilol (Coreg) is a β-blocker that hasa unique pharmacological profile. Like labetalol, it is aβ-blocker that possesses α1-blocking activity. Only the(S) enantiomer possesses the β-blocking activity, althoughboth enantiomers are blockers of the α1-receptor. Overall,its β-blocking activity is 10- to 100-fold of its α-blocking activity.
Biological ActivityPotent β -adrenoceptor and α 1 -adrenoceptor antagonist (K i values are 0.81, 0.96 and 2.2 nM for β 1 -, β 2 - and α 1 -adrenoceptors respectively) that displays antihypertensive and peripheral vasodilatory activity. Blocks cardiac inward-rectifier K + (K IR ) channels, voltage-dependent Ca 2+ channels and exhibits antioxidant properties at higher concentrations.
Biochem/physiol ActionsCavedilol is a non-selective β-adrenergic blocker with α1 blocking activity. Carvedilol is used specifically for the treatment of heart failure and high blood pressure. It has been shown to improve left ventricular ejection fraction and may reduce mortality.
Clinical UseCarvedilol is also unique in that it possesses antioxidantactivity and an antiproliferative effect on vascular smoothmuscle cells. It thus has a neuroprotective effect and the abilityto provide major cardiovascular organ protection. It isused in treating hypertension and congestive heart failure.
Veterinary Drugs and TreatmentsCarvedilol may be useful as adjunctive therapy in the treatment of heart failure (dilated cardiomyopathy) in dogs. There is a fair amount of controversy at present among veterinary cardiologists as to whether this drug will find a therapeutic niche.
in vitrocarvedilol potently inhibited fe2+-initiated lipid peroxidation in rat brain homogenate with an ic50 of 8.1 μm. in rat brain homogenate, carvedilol protected against fe2+-induced α-tocopherol depletion with an ic50 of 17.6 μm. carvedilol dose-dependently decreased the intensity of the dmpo-oh signal, with an ic50 of 25 μm [1]. carvedilol prevented vascular smooth muscle cell migration, proliferation, and neointimal formation following vascular injury. in human cultured pulmonary artery vascular smooth muscle cells, carvedilol (0.1-10 μm) concentration-dependently inhibited the mitogenesis stimulated by platelet-derived growth factor, epidermal growth factor, thrombin, and serum, with ic50 values ranging from 0.3 to 2.0 μm. carvedilol concentration-dependently inhibited vascular smooth muscle cell migration induced by platelet-derived growth factor with an ic50 value of 3 μm [3].
Drug interactionsPotentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: NSAIDs antagonise hypotensive effect. Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; increased risk of myocardial depression and bradycardia with flecainide.
Antibacterials: concentration reduced by rifampicin.
Antidepressants: enhanced hypotensive effect with MAOIs.
Antihypertensives; enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin.
Antimalarials: increased risk of bradycardia with mefloquine.
Antipsychotics enhanced hypotensive effect with phenothiazines.
Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil.
Ciclosporin: increased trough concentration, reduce dose by 20% in affected patients.
Cytotoxics: possible increased risk of bradycardia with crizotinib. Diuretics: enhanced hypotensive effect. Fingolimod: possibly increased risk of bradycardia. Moxisylyte: possible severe postural hypotension. Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.







MetabolismCarvedilol is subject to considerable first-pass metabolism in the liver; the absolute bioavailability is about 25%. It is extensively metabolised in the liver, primarily by the cytochrome P450 isoenzymes CYP2D6 and CYP2C9, and the metabolites are excreted mainly in the bile.
storageStore at +4°C
phenoxybenzamine Ethanol 2-Methoxyethanol Anisole Ethylparaben (Trifluoromethoxy)benzene 3-(METHOXYMETHOXY)BENZALDEHYDE p-Anisic acid p-Anisidine Diethyl ether Ethyl acetate p-Anisaldehyde (R)-(+)-CARVEDILOL 4-Methoxyphenol Carvedilol Ethyl acrylate 5'-HYDROXYPHENYL CARVEDILOL 1-Propanol

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.