QuickView for Carvedilol (compound)

Summary
General Info

PubChem

PubChem Compound 185394

Name:	carvedilol
PubChem Compound ID:	185394
Molecular formula:	C₂₄H₂₆N₂O₄
Molecular weight:	406.474 g/mol
Synonyms:	95093-99-5

DrugBank

Identification

Name:	carvedilol
Name (isomeric):	DB01136
Drug Type:	small molecule
Synonyms:	Carvedilolum [Latin]
Brand:	Coreg CR, Coreg
Category:	Vasodilator Agents, Adrenergic Agents, Adrenergic beta-Antagonists, Adrenergic alpha-Antagonists, Antihypertensive Agents
CAS number:	72956-09-3

Pharmacology

Indication:	For the treatment of mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin.
Pharmacology:	Carvedilol is a nonselective beta-adrenergic blocking agent with alpha1-blocking activity and is indicated for the treatment of hypertension and mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin. Carvedilol is a racemic mixture in which nonselective b-adrenoreceptor blocking activity is present in the S(-) ... show more » Carvedilol is a nonselective beta-adrenergic blocking agent with alpha1-blocking activity and is indicated for the treatment of hypertension and mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin. Carvedilol is a racemic mixture in which nonselective b-adrenoreceptor blocking activity is present in the S(-) enantiomer and a-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol has no intrinsic sympathomimetic activity. The effect of carvedilol's b-adrenoreceptor blocking activity has been demonstrated in animal and human studies showing that carvedilol (1) reduces cardiac output in normal subjects; (2) reduces exercise-and/or isoproterenol-induced tachycardia and (3) reduces reflex orthostatic tachycardia. show less «
Mechanism of Action:	Carvedilol is a racemic mixture in which nonselective beta-adrenoreceptor blocking activity is present in the S(-) enantiomer and alpha-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol's beta-adrenergic receptor blocking ability decreases the heart rate, myocardial contractility, and myocardial ... show more » Carvedilol is a racemic mixture in which nonselective beta-adrenoreceptor blocking activity is present in the S(-) enantiomer and alpha-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol's beta-adrenergic receptor blocking ability decreases the heart rate, myocardial contractility, and myocardial oxygen demand. Carvedilol also decreases systemic vascular resistance via its alpha adrenergic receptor blocking properties. Carvedilol and its metabolite BM-910228 (a less potent beta blocker, but more potent antioxidant) have been shown to restore the inotropic responsiveness to Ca²⁺ in OH^- free radical-treated myocardium. Carvedilol and its metabolites also prevent OH^- radical-induced decrease in sarcoplasmic reticulum Ca²⁺-ATPase activity. Therefore, carvedilol and its metabolites may be beneficial in chronic heart failure by preventing free radical damage. show less «
Absorption:	Carvedilol is rapidly and extensively absorbed following oral administration, with an absolute bioavailability of approximately 25% to 35% due to a significant degree of first-pass metabolism.
Protein binding:	98%
Biotransformation:	Hepatic. Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation. Demethylation and hydroxylation at the phenol ring produce three active metabolites with b-receptor blocking activity. The 4'-hydroxyphenyl metabolite is approximately 13 times more potent than carvedilol for b-blockade.
Route of elimination:	Carvedilol is extensively metabolized. Less than 2% of the dose was excreted unchanged in the urine. Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation. The metabolites of carvedilol are excreted primarily via the bile into the feces.
Half Life:	7-10 hours
Clearance:	500-700 mL/min
Toxicity:	Not expected to be toxic following ingestion.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take with food, food slows the absorption rate and reduces the incidence of adverse effects (extent of absorption is not affected).

Drug interaction:

Ibuprofen	Risk of inhibition of renal prostaglandins
Glisoxepide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Procaterol	Antagonism
Citalopram	The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
Salmeterol	Antagonism

Ibuprofen	Risk of inhibition of renal prostaglandins
Glisoxepide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Procaterol	Antagonism
Citalopram	The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
Salmeterol	Antagonism
Fluoxetine	The SSRI, fluoxetine, may increase the bradycardic effect of the beta-blocker, carvedilol.
Insulin Detemir	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Glycodiazine	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Terbinafine	Terbinafine may reduce the metabolism and clearance of Carvedilol. Consider alternate therapy or monitor for therapeutic/adverse effects of Carvedilol if Terbinafine is initiated, discontinued or dose changed.
Fenoterol	Antagonism
Acetohexamide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Pipobroman	Antagonism
Orciprenaline	Antagonism
Isoproterenol	Antagonism
Pirbuterol	Antagonism
Tolbutamide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Glipizide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Prazosin	Risk of hypotension at the beginning of therapy
Insulin Aspart	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Glyburide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Gliclazide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Insulin	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Piroxicam	Risk of inhibition of renal prostaglandins
Digoxin	Carvedilol may increase the serum levels and effect of digoxin.
Insulin Lispro	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Indomethacin	Risk of inhibition of renal prostaglandins
Ergonovine	Ischemia with risk of gangrene
Ergotamine	Ischemia with risk of gangrene
Sertraline	The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, carvedilol.
Epinephrine	Hypertension, then bradycardia
Clonidine	Increased hypertension when clonidine stopped
Terazosin	Increased risk of hypotension. Initiate concomitant therapy cautiously.
Cyclosporine	Carvedilol may increase the therapeutic and adverse effects of cyclosporine.
Escitalopram	The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, carvedilol.
Terbutaline	Antagonism
Methysergide	Ischemia with risk of gangrene
Treprostinil	Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Chlorpropamide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Salbutamol	Antagonism
Formoterol	Antagonism
Dihydroergotamine	Ischemia with risk of gangrene
Insulin Glulisine	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Dihydroergotoxine	Ischemia with risk of gangrene
Repaglinide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Disopyramide	The beta-blocker, carvedilol, may increase the toxicity of disopyramide.
Paroxetine	The SSRI, paroxetine, may increase the bradycardic effect of the beta-blocker, carvedilol.
Verapamil	Increased effect of both drugs
Insulin Glargine	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
Topotecan	The p-glycoprotein inhibitor, Carvedilol, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
Lidocaine	The beta-blocker, carvedilol, may increase the effect and toxicity of lidocaine.
Tolazamide	The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.