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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
Levosimendan.
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
Carvedilol--a new dimension in pediatric heart failure therapy.
2001 Apr
50th Annual scientific sessions of the American college of cardiology.
2001 Apr 10
Reducing readmissions for congestive heart failure.
2001 Apr 15
Detection of low levels of the amorphous phase in crystalline pharmaceutical materials by thermally stimulated current spectrometry.
2001 Jan
[Effects of carvedilol in rats with induced chronic kidney failure].
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
Stereoselective effects of (R)- and (S)-carvedilol in humans.
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
Beta-blockers to reduce mortality in patients with systolic dysfunction: a meta-analysis.
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
Influence of carvedilol on the benefits of physical training in patients with moderate chronic heart failure.
2001 Jun
Carvedilol increases plasma vascular endothelial growth factor (VEGF) in patients with chronic heart failure.
2001 Jun
Plasma brain natriuretic peptide as a novel therapeutic indicator in idiopathic dilated cardiomyopathy during beta-blocker therapy: a potential of hormone-guided treatment.
2001 Jun
Comparative effects of carvedilol and metoprolol on left ventricular ejection fraction in heart failure: results of a meta-analysis.
2001 Jun
Plasma N-terminal pro-brain natriuretic peptide and adrenomedullin: prognostic utility and prediction of benefit from carvedilol in chronic ischemic left ventricular dysfunction. Australia-New Zealand Heart Failure Group.
2001 Jun 1
Protective effect of carvedilol on chenodeoxycholate induction of the permeability transition pore.
2001 Jun 1
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
Determination of carvedilol in human cardiac tissue by high-performance liquid chromatography.
2001 Mar
[Severe heart failure. Carvedilol lowers mortality].
2001 Mar 1
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
Mechanisms of carvedilol action in human congestive heart failure.
2001 May
Overview of the results of recent beta blocker trials.
2001 May
Influence of carvedilol on hospitalizations in heart failure: incidence, resource utilization and costs. U.S. Carvedilol Heart Failure Study Group.
2001 May
Carvedilol in the treatment of chronic heart failure.
2001 May
Carvedilol versus other beta-blockers in heart failure.
2001 May
Myocardial free fatty acid and glucose use after carvedilol treatment in patients with congestive heart failure.
2001 May 22
Racial differences in the response to drugs--pointers to genetic differences.
2001 May 3
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
Separation of carvedilol enantiomers in very small volumes of human plasma by capillary electrophoresis with laser-induced fluorescence.
2001 May 5
Effect of carvedilol on outcome after myocardial infarction in patients with left-ventricular dysfunction: the CAPRICORN randomised trial.
2001 May 5
Current role of beta-adrenergic blockers in the management of chronic heart failure.
2001 May 7
Economic impact of beta blockade in heart failure.
2001 May 7
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 Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
NDF-RT N0000175556
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
LIVERTOX 153
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
NDF-RT N0000175553
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
WHO-VATC QC07AG02
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
NDF-RT N0000009924
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
WHO-ATC C07AG02
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
NDF-RT N0000000099
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
Code System Code Type Description
ChEMBL
CHEMBL723
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
EPA CompTox
72956-09-3
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
MESH
C043211
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
NCI_THESAURUS
C28906
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
DRUG BANK
DB01136
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
LactMed
72956-09-3
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
JAPANESE REVIEW
ARTIST
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY APPROVED AUGUST 2015
RXCUI
20352
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY RxNorm
EVMPD
SUB06153MIG
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
IUPHAR
551
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
MERCK INDEX
M3143
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY Merck Index
HSDB
72956-09-3
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
WIKIPEDIA
Carvedilol
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
PUBCHEM
2585
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY SWITZERF
INN
5333
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY
CAS
72956-09-3
Created by admin on Tue Mar 06 10:26:21 UTC 2018 , Edited by admin on Tue Mar 06 10:26:21 UTC 2018
PRIMARY