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Details

Stereochemistry RACEMIC
Molecular Formula 2C24H26N2O4.H2O.2H3O4P
Molecular Weight 1026.9541
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARVEDILOL PHOSPHATE

SMILES

O.OP(O)(O)=O.OP(O)(O)=O.COC1=CC=CC=C1OCCNCC(O)COC2=CC=CC3=C2C4=C(N3)C=CC=C4.COC5=CC=CC=C5OCCNCC(O)COC6=C7C(NC8=C7C=CC=C8)=CC=C6

InChI

InChIKey=LHNYXTULDSJZRB-UHFFFAOYSA-N
InChI=1S/2C24H26N2O4.2H3O4P.H2O/c2*1-28-21-10-4-5-11-22(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;2*1-5(2,3)4;/h2*2-12,17,25-27H,13-16H2,1H3;2*(H3,1,2,3,4);1H2

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 ( + / - )

Molecular Formula H3O4P
Molecular Weight 97.9952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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 Oct 22 00:17:16 UTC 2019
Edited
by admin
on Tue Oct 22 00:17:16 UTC 2019
Record UNII
EQT531S367
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARVEDILOL PHOSPHATE
ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
SKF 105517D
Code English
CARVEDILOL PHOSPHATE HYDRATE [JAN]
Common Name English
CARVEDILOL DIHYDROGEN PHOSPHATE HEMIHYDRATE
Common Name English
CARVEDILOL PHOSPHATE HEMIHYDRATE
WHO-DD  
Common Name English
CARVEDILOL PHOSPHATE [VANDF]
Common Name English
2-PROPANOL, 1-(9H-CARBAZOL-4-YLOXY)-3-((2-(2-METHOXYPHENOXY)ETHYL)AMINO) , PHOSPHATE (SALT), HYDRATE (2:2:1)
Common Name English
COREG CR
Brand Name English
CARVEDILOL PHOSPHATE HYDRATE
JAN  
Common Name English
CARVEDILOL PHOSPHATE [USAN]
Common Name English
CARVEDILOL PHOSPHATE [ORANGE BOOK]
Common Name English
SKF-105517D
Code English
(2RS)-1-(9H-CARBAZOL-4-YLOXY)-3-((2-(2-METHOXYPHENOXY)ETHYL)AMINO)PROPAN-2-OL PHOSPHATE SALT (1:1) HEMIHYDRATE
Common Name English
SK&F-105517-D
Code English
CARVEDILOL PHOSPHATE HEMIHYDRATE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
Code System Code Type Description
PUBCHEM
11954344
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
PRIMARY
CAS
610309-89-2
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
PRIMARY
RXCUI
668310
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C65292
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
PRIMARY
EVMPD
SUB25804
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
PRIMARY
ChEMBL
CHEMBL723
Created by admin on Tue Oct 22 00:17:16 UTC 2019 , Edited by admin on Tue Oct 22 00:17:16 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY