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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

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

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
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
Using isoproterenol stress echocardiography to predict the response to carvedilol in patients with dilated cardiomyopathy.
2001 Jun
Beta-blocker trials seem to be in conflict.
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
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.
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:26:21 UTC 2018
Edited
by admin
on Tue Mar 06 10:26:21 UTC 2018
Record UNII
0K47UL67F2
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
TARGET -> AGONIST
BINDER -> LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TARGET -> AGONIST
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PARENT
M2 possess approximately 2.5 times more potency.
PLASMA
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC