U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C24H26N2O4
Molecular Weight 406.4751
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARVEDILOL

SMILES

COc1ccccc1OCCNCC(COc2cccc3c2c4ccccc4[nH]3)O

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
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.

Originator

Curator's Comment:: reference retrieved from http://www.drugfuture.com/chemdata/carvedilol.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COREG

Approved Use

COREG® (carvedilol) is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization. COREG is indicated to reduce cardiovascular mortality in clinically stable patients who have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of ≤40% (with or without symptomatic heart failure). COREG is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.

Launch Date

811036800000
Primary
COREG

Approved Use

COREG® (carvedilol) is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization. COREG is indicated to reduce cardiovascular mortality in clinically stable patients who have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of ≤40% (with or without symptomatic heart failure). COREG is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.

Launch Date

811036800000
Primary
COREG

Approved Use

COREG® (carvedilol) is indicated for the treatment of mild-to-severe chronic heart failure of ischemic or cardiomyopathic origin, usually in addition to diuretics, ACE inhibitors, and digitalis, to increase survival and, also, to reduce the risk of hospitalization. COREG is indicated to reduce cardiovascular mortality in clinically stable patients who have survived the acute phase of a myocardial infarction and have a left ventricular ejection fraction of ≤40% (with or without symptomatic heart failure). COREG is indicated for the management of essential hypertension. It can be used alone or in combination with other antihypertensive agents, especially thiazide-type diuretics.

Launch Date

811036800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
18.4 ng/mL
6.25 mg 2 times / day steady-state, oral
dose: 6.25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CARVEDILOL, (+)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
8.46 ng/mL
6.25 mg 2 times / day steady-state, oral
dose: 6.25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CARVEDILOL, (-)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
26.5 ng/mL
6.25 mg 2 times / day steady-state, oral
dose: 6.25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CARVEDILOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
94.3 ng × h/mL
6.25 mg 2 times / day steady-state, oral
dose: 6.25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CARVEDILOL, (+)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
42.2 ng × h/mL
6.25 mg 2 times / day steady-state, oral
dose: 6.25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CARVEDILOL, (-)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
139 ng × h/mL
6.25 mg 2 times / day steady-state, oral
dose: 6.25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CARVEDILOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
unknown, 41 years
Health Status: unknown
Age Group: 41 years
Sex: M
Sources:
Other AEs: Wheezing...
Other AEs:
Wheezing (1 patient)
Sources:
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 66.7±12.0 years
Health Status: unhealthy
Age Group: 66.7±12.0 years
Sex: M+F
Sources:
375 mg single, oral
Overdose
Dose: 375 mg
Route: oral
Route: single
Dose: 375 mg
Sources:
unhealthy, 84 years
Health Status: unhealthy
Age Group: 84 years
Sex: M
Sources:
Other AEs: Hypotension...
Other AEs:
Hypotension (1 patient)
Sources:
50 mg 1 times / day steady, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Hypotension...
AEs leading to
discontinuation/dose reduction:
Hypotension (0.7%)
Sources:
20 mg 2 times / day multiple, oral
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
unhealthy, adult
Disc. AE: Congestive cardiac failure...
AEs leading to
discontinuation/dose reduction:
Congestive cardiac failure (moderate, 1 patient)
Sources:
25 mg 2 times / day steady, oral
Dose: 25 mg, 2 times / day
Route: oral
Route: steady
Dose: 25 mg, 2 times / day
Sources:
unhealthy, adult
Disc. AE: Dizziness...
AEs leading to
discontinuation/dose reduction:
Dizziness (1.3%)
Sources:
6.25 mg 2 times / day multiple, oral
Dose: 6.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 6.25 mg, 2 times / day
Sources:
unhealthy, adult
Disc. AE: Abdominal distension...
AEs leading to
discontinuation/dose reduction:
Abdominal distension (1 patient)
Sources:
6.25 mg 2 times / day multiple, oral
Dose: 6.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 6.25 mg, 2 times / day
Sources:
unhealthy, adult
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (moderate, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Wheezing 1 patient
300 mg single, oral
Overdose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
unknown, 41 years
Health Status: unknown
Age Group: 41 years
Sex: M
Sources:
Hypotension 1 patient
375 mg single, oral
Overdose
Dose: 375 mg
Route: oral
Route: single
Dose: 375 mg
Sources:
unhealthy, 84 years
Health Status: unhealthy
Age Group: 84 years
Sex: M
Sources:
Hypotension 0.7%
Disc. AE
50 mg 1 times / day steady, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg, 1 times / day
Sources:
unhealthy, adult
Congestive cardiac failure moderate, 1 patient
Disc. AE
20 mg 2 times / day multiple, oral
Dose: 20 mg, 2 times / day
Route: oral
Route: multiple
Dose: 20 mg, 2 times / day
Sources:
unhealthy, adult
Dizziness 1.3%
Disc. AE
25 mg 2 times / day steady, oral
Dose: 25 mg, 2 times / day
Route: oral
Route: steady
Dose: 25 mg, 2 times / day
Sources:
unhealthy, adult
Abdominal distension 1 patient
Disc. AE
6.25 mg 2 times / day multiple, oral
Dose: 6.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 6.25 mg, 2 times / day
Sources:
unhealthy, adult
Rash moderate, 1 patient
Disc. AE
6.25 mg 2 times / day multiple, oral
Dose: 6.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 6.25 mg, 2 times / day
Sources:
unhealthy, adult
PubMed

PubMed

TitleDatePubMed
Carvedilol prevents remodeling in patients with left ventricular dysfunction after acute myocardial infarction.
1999 Apr
Statins and peripheral neuropathy.
1999 Jan
Carvedilol enhances atrial and brain natriuretic peptide mRNA expression and release in rat heart.
2000
[Clinical efficacy of carvedilol in patients with severe cardiac insufficiency].
2001
50th Annual scientific sessions of the American college of cardiology.
2001 Apr 10
Reducing readmissions for congestive heart failure.
2001 Apr 15
Variceal bleeding and portal hypertension: still a therapeutic challenge?
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
Antiarrhythmic drug carvedilol inhibits HERG potassium channels.
2001 Feb 1
A placebo controlled evaluation of the antifibrillatory effects of carvedilol.
2001 Jan
Sexual activity in hypertensive men treated with valsartan or carvedilol: a crossover study.
2001 Jan
Recovery of the cardiac adrenergic nervous system after long-term beta-blocker therapy in idiopathic dilated cardiomyopathy: assessment by increase in myocardial 123I-metaiodobenzylguanidine uptake.
2001 Jan
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.
2001 Jan
Current role of beta-adrenergic blockers in the treatment of chronic congestive heart failure.
2001 Jan 15
Inhibition of heart mitochondrial lipid peroxidation by non-toxic concentrations of carvedilol and its analog BM-910228.
2001 Jan 15
Effect of carvedilol on atrioventricular conduction in the ischemic heart.
2001 Jan 26
[Effects of carvedilol in rats with induced chronic kidney failure].
2001 Jan-Feb
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
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
Nebivolol, carvedilol and metoprolol do not influence cardiac Ca(2+) sensitivity.
2001 Jun 22
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
Mechanisms of carvedilol action in human congestive heart failure.
2001 May
Carvedilol in the treatment of chronic heart failure.
2001 May
Racial differences in the response to drugs--pointers to genetic differences.
2001 May 3
Current role of beta-adrenergic blockers in the management of chronic heart failure.
2001 May 7
Patents

Sample Use Guides

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 afterintervals 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
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 [VANDF]
Common Name English
CARVEDILOL [USAN]
Common Name English
BM-14.190
Code English
NSC-758694
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
CARVEDILOL [EP MONOGRAPH]
Common Name 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
QUERTO
Brand Name English
(+/-)-1-CARBAZOL-4-YLOXY)-3-((2-(O-METHOXYPHENOXY)ETHYL)AMINO)-2-PROPANOL
Common Name English
CARVEDILOL [INN]
Common Name English
CARVEDILOL [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009923
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
NDF-RT N0000175556
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
WHO-ATC C07FX06
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
LIVERTOX 153
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
NDF-RT N0000175553
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
WHO-VATC QC07AG02
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
NDF-RT N0000009924
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
NCI_THESAURUS C29576
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
WHO-ATC C07AG02
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
NDF-RT N0000000099
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL723
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
EPA CompTox
72956-09-3
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
MESH
C043211
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
NCI_THESAURUS
C28906
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
DRUG BANK
DB01136
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
LACTMED
Carvedilol
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
DRUG CENTRAL
522
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
JAPANESE REVIEW
ARTIST
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY APPROVED AUGUST 2015
RXCUI
20352
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY RxNorm
EVMPD
SUB06153MIG
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
IUPHAR
551
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
MERCK INDEX
M3143
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY Merck Index
FDA UNII
0K47UL67F2
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
HSDB
7044
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
USP_CATALOG
1096622
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
Carvedilol
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
PUBCHEM
2585
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
INN
5333
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY
CAS
72956-09-3
Created by admin on Fri Jun 25 21:01:42 UTC 2021 , Edited by admin on Fri Jun 25 21:01:42 UTC 2021
PRIMARY