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Details

Stereochemistry RACEMIC
Molecular Formula C24H26N2O4
Molecular Weight 406.4742
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARVEDILOL

SMILES

COC1=CC=CC=C1OCCNCC(O)COC2=CC=CC3=C2C4=C(N3)C=CC=C4

InChI

InChIKey=OGHNVEJMJSYVRP-UHFFFAOYSA-N
InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3

HIDE SMILES / InChI

Description

Carvedilol competitively blocks β1, β2 and α1 receptors. The drug lacks sympathomimetic activity and has vasodilating properties that are exerted primarily through α1-blockade. Animal models indicate that carvedilol confers protection against myocardial necrosis, arrhythmia and cell damage caused by oxidising free radicals, and the drug has no adverse effects on plasma lipid profiles. COREG® (carvedilol) is a racemic mixture in which nonselective β-adrenoreceptor blocking activity is present in the S(-) enantiomer and α1-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol is the first drug of its kind to be approved for the treatment of congestive heart failure, and is now the standard of care for this devastating disease. Carvedilol is also confirmed as effective in the management of mild to moderate hypertension and ischaemic heart disease.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Protective effects of carvedilol against doxorubicin-induced cardiomyopathy in rats.
1999
Potent and selective human beta(3)-adrenergic receptor antagonists.
1999 Aug
Hypotension with dobutamine: beta-adrenergic antagonist selectivity at low doses of carvedilol.
1999 Dec
Carvedilol and lacidipine prevent cardiac hypertrophy and endothelin-1 gene overexpression after aortic banding.
1999 Dec
Carvedilol reduces ischaemic skeletal muscle necrosis.
1999 Sep
Differential remodeling of the left and right heart after norepinephrine treatment in rats: studies on cytokines and collagen.
2000 Feb
Carvedilol affects the physiological and behavioral response to smoked cocaine in humans.
2000 Jul 1
Beta-blockers of the third generation inhibit endothelin-1 liberation, mRNA production and proliferation of human coronary smooth muscle and endothelial cells.
2000 Nov
Comitogenic effect of catecholamines on rat cardiac fibroblasts in culture.
2000 Nov
Improvement in cardiac function and free fatty acid metabolism in a case of dilated cardiomyopathy with CD36 deficiency.
2000 Sep
[Clinical efficacy of carvedilol in patients with severe cardiac insufficiency].
2001
CAPRICORN: a story of alpha allocation and beta-blockers in left ventricular dysfunction post-MI.
2001 Apr
Characterization of beta(1)-selectivity, adrenoceptor-G(s)-protein interaction and inverse agonism of nebivolol in human myocardium.
2001 Apr
Carvedilol as therapy in pediatric heart failure: an initial multicenter experience.
2001 Apr
[Economic study of carvedilol in heart failure. A cost effectiveness study in France].
2001 Feb
Dilated cardiomyopathy in dialysis patients--beneficial effects of carvedilol: a double-blind, placebo-controlled trial.
2001 Feb
Differential effects of carvedilol and metoprolol on isoprenaline-induced changes in beta-adrenoceptor density and systolic function in rat cardiac myocytes.
2001 Feb 1
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.
2001 Jan
Effect of carvedilol on atrioventricular conduction in the ischemic heart.
2001 Jan 26
Iodine-123 MIBG imaging before treatment of heart failure with carvedilol to predict improvement of left ventricular function and exercise capacity.
2001 Jan-Feb
Effects of carvedilol on left ventricular function, mass, and scintigraphic findings in isolated left ventricular non-compaction.
2001 Jul
Catecholamines stimulate interleukin-6 synthesis in rat cardiac fibroblasts.
2001 Jul
Radical-scavenging and iron-chelating properties of carvedilol, an antihypertensive drug with antioxidative activity.
2001 Jul 15
Using isoproterenol stress echocardiography to predict the response to carvedilol in patients with dilated cardiomyopathy.
2001 Jun
Bucindolol, a nonselective beta 1- and beta 2-adrenergic receptor antagonist, decreases beta-adrenergic receptor density in cultured embryonic chick cardiac myocyte membranes.
2001 Jun
Clinical Trials Update: CAPRICORN, COPERNICUS, MIRACLE, STAF, RITZ-2, RECOVER and RENAISSANCE and cachexia and cholesterol in heart failure. Highlights of the Scientific Sessions of the American College of Cardiology, 2001.
2001 Jun
A cost-effectiveness analysis of bisoprolol for heart failure.
2001 Jun
Differing beta-blocking effects of carvedilol and metoprolol.
2001 Jun
Carvedilol increases plasma vascular endothelial growth factor (VEGF) in patients with chronic heart failure.
2001 Jun
Beta-blocker trials seem to be in conflict.
2001 Jun 12
Beta-blockade in chronic heart failure.
2001 Jun 12
Relationship between tumor necrosis factor-alpha production and oxidative stress in the failing hearts of patients with dilated cardiomyopathy.
2001 Jun 15
Nebivolol, carvedilol and metoprolol do not influence cardiac Ca(2+) sensitivity.
2001 Jun 22
Random research.
2001 Jun 26
[Options in drug combinations].
2001 Mar
[Adrenergic beta inhibitors in heart insufficiency: which and when?].
2001 Mar
Predicting response to carvedilol for the treatment of heart failure: a multivariate retrospective analysis.
2001 Mar
Extracellular matrix proteins in cardiac fibroblasts derived from rat hearts with chronic pressure overload: effects of beta-receptor blockade.
2001 Mar
What is the optimal medical management of ischemic heart failure?
2001 Mar-Apr
Benefits of beta-blockers in heart failure: a class specific effect?
2001 May
Does intention-to-treat analysis answer all questions in long-term mortality trials? Considerations on the basis of the ANZ trial.
2001 May
Carvedilol in the treatment of chronic heart failure.
2001 May
Myocardial free fatty acid and glucose use after carvedilol treatment in patients with congestive heart failure.
2001 May 22
Race and the response to adrenergic blockade with carvedilol in patients with chronic heart failure.
2001 May 3
Expanding indications for beta-blockers in heart failure.
2001 May 31
Effect of carvedilol on survival in severe chronic heart failure.
2001 May 31
Patents

Sample Use Guides

In Vivo Use Guide
Take with food. Individualize dosage and monitor during up-titration. • Heart failure: Start at 3.125 mg twice daily and increase to 6.25, 12.5, and then 25 mg twice daily over intervals of at least 2 weeks. Maintain lower doses if higher doses are not tolerated. • Left ventricular dysfunction following myocardial infarction: Start at 6.25 mg twice daily and increase to 12.5 mg then 25 mg twice daily after intervals of 3 to 10 days. A lower starting dose or slower titration may be used. • Hypertension: Start at 6.25 mg twice daily and increase if needed for blood pressure control to 12.5 mg then 25 mg twice daily over intervals of 1 to 2 weeks.
Route of Administration: Oral
In Vitro Use Guide
Compared with the PDGF-stimulated control, DNA synthesis decreased significantly to 60.3% +/- 10.4% and 18.3% +/- 5.9% in the presence of 1 and 10 microM of carvedilol, respectively (P < 0.05, each). Carvedilol significantly inhibited the activity of VSMCs stimulated by ET-1 and ANG-II. The IC50 of carvedilol was 1-10 microM. CsA only inhibited VSMCs significantly in the PDGF-stimulated subgroup. The addition of CsA in the presence of carvedilol did not affect the inhibitory activity of carvedilol. The pattern of inhibition in the combined group was uniform and similar to that of the carvedilol alone group, regardless of the stimulator used.
Name Type Language
CARVEDILOL
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
CARVEDILOL [EP]
Common Name English
CARVEDILOL [VANDF]
Common Name English
CARVEDILOL [USAN]
Common Name English
BM-14.190
Code English
KREDEX
Brand Name English
2-PROPANOL, 1-(9H-CARBAZOL-4-YLOXY)-3-((2-(2-METHOXYPHENOXY)ETHYL)AMINO)-, (+/-)-
Systematic Name English
TALLITON
Common Name English
CARVEDILOL [MI]
Common Name English
CARVEDILOL [ORANGE BOOK]
Common Name English
CORONIS
Common Name English
BM 14.190
Code English
DILATREND
Brand Name English
C07AG02
Code English
CARVEDILOL [MART.]
Common Name English
SKF-105517
Code English
COREG
Brand Name English
1-(CARBAZOL-4-YLOXY)-3-((2-(O-METHOXY-PHENOXY)ETHYL)AMINO)-2-PROPANOL
Common Name English
KORVASAN
Common Name English
CARVEDILOL [HSDB]
Common Name English
DQ-2466
Code English
ARTIST
Brand Name English
DIMITONE
Brand Name English
CARVEDILOL [JAN]
Common Name English
EUCARDIC
Brand Name English
CARVEDILOL [USP-RS]
Common Name English
CARVEDILOL [WHO-DD]
Common Name English
BM-14190
Code English
BM-14-190
Code English
SK&F-105517
Code English
CARVEDILOL [USP]
Common Name English
QUERTO
Brand Name English
(+/-)-1-CARBAZOL-4-YLOXY)-3-((2-(O-METHOXYPHENOXY)ETHYL)AMINO)-2-PROPANOL
Common Name English
CARVEDILOL [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009923
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
NDF-RT N0000175556
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
WHO-ATC C07FX06
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
LIVERTOX 153
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
NDF-RT N0000175553
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
WHO-VATC QC07AG02
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
NDF-RT N0000009924
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
NCI_THESAURUS C29576
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
WHO-ATC C07AG02
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
NDF-RT N0000000099
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL723
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
EPA CompTox
72956-09-3
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
MESH
C043211
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
NCI_THESAURUS
C28906
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
DRUG BANK
DB01136
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
LactMed
72956-09-3
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
JAPANESE REVIEW
ARTIST
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY APPROVED AUGUST 2015
RXCUI
20352
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY RxNorm
EVMPD
SUB06153MIG
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
IUPHAR
551
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
MERCK INDEX
M3143
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY Merck Index
HSDB
72956-09-3
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
WIKIPEDIA
Carvedilol
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
PUBCHEM
2585
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
INN
5333
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY
CAS
72956-09-3
Created by admin on Tue Oct 22 00:17:17 UTC 2019 , Edited by admin on Tue Oct 22 00:17:17 UTC 2019
PRIMARY